2-Fluorobenzonitrile by Asch

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2 substances in Reaxys

2017-09-30 13h:32m:16s (EST)

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Search as: As drawn, No mixtures, No charges, No radicals

1/17

2017-09-30 13:53:58

Reaxys ID 2042184 View in Reaxys

1/2 CAS Registry Number: 394-47-8 Chemical Name: 2- fluorobenzonitrile; o-fluorobenzonitrile Linear Structure Formula: NCC6H4F Molecular Formula: C7H4FN Molecular Weight: 121.114 Type of Substance: isocyclic InChI Key: GDHXJNRAJRCGMX-UHFFFAOYSA-N Note:

F N

Substance Label (83) Label References 2m

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10-F

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III

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11l

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Shi, Shicheng; Szostak, Michal; Organic Letters; vol. 19; nb. 12; (2017); p. 3095 - 3098, View in Reaxys

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Sivakami; Babu, S. Ganesh; Dhanuskodi; Karvembu; RSC Advances; vol. 5; nb. 12; (2015); p. 8571 8578, View in Reaxys

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1: 1a

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Ryan, Sarah J.; Schimler, Sydonie D.; Bland, Douglas C.; Sanford, Melanie S.; Organic Letters; vol. 17; nb. 8; (2015); p. 1866 - 1869, View in Reaxys

Table 3, Entry 16

Xu, Zhicheng; Xiao, Yunqing; Ding, Hong; Cao, Changsheng; Li, Haitao; Pang, Guangsheng; Shi, Yanhui; Synthesis (Germany); vol. 47; nb. 11; (2015); p. 1560 - 1566; Art.No: SS-2014-F0771-OP, View in Reaxys

a10

Lin, Hong-Yan; Li, Zi-Kang; Bai, Li-Fei; Baloch, Shahla Karim; Wang, Fang; Qiu, Han-Yue; Wang, Xue; Qi, Jin-Liang; Yang, Raong-Wu; Wang, Xiao-Ming; Yang, Yong-Hua; Biochemical Pharmacology; vol. 96; nb. 2; (2015); p. 93 - 106, View in Reaxys

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14g

Bagley, Mark C.; Dwyer, Jessica E.; Molina, Maria D. Beltran; Rand, Alexander W.; Rand, Hayley L.; Tomkinson, Nicholas C. O.; Organic and Biomolecular Chemistry; vol. 13; nb. 24; (2015); p. 6814 - 6824, View in Reaxys

17e

Guan, Qi; Feng, Dongjie; Bai, Zhaoshi; Cui, Yuanhang; Zuo, Daiying; Zhai, Min'An; Jiang, Xuewei; Zhou, Wenbo; Bao, Kai; Wu, Yingliang; Zhang, Weige; MedChemComm; vol. 6; nb. 8; (2015); p. 1484 1493, View in Reaxys

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Lauria, Antonino; Alfio, Alessia; Bonsignore, Riccardo; Gentile, Carla; Martorana, Annamaria; Gennaro, Giuseppe; Barone, Giampaolo; Terenzi, Alessio; Almerico, Anna Maria; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 15; (2014); p. 3291 - 3297, View in Reaxys

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Yin, Wenzhu; Liu, Rui; He, Guangke; Lv, Wangjie; Zhu, Hongjun; RSC Advances; vol. 4; nb. 71; (2014); p. 37773 - 37778, View in Reaxys

20g

Jones-Mensah, Ebenezer; Magolan, Jakob; Tetrahedron Letters; vol. 55; nb. 38; (2014); p. 5323 - 5326, View in Reaxys

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Procopiou, Panayiotis A.; Barrett, John W.; Barton, Nicholas P.; Begg, Malcolm; Clapham, David; Copley, Royston C. B.; Ford, Alison J.; Graves, Rebecca H.; Hall, David A.; Hancock, Ashley P.; Hill, Alan P.; Hobbs, Heather; Hodgson, Simon T.; Jumeaux, Coline; Lacroix, Yannick M. L.; Miah, Afjal H.; Morriss, Karen M. L.; Needham, Deborah; Sheriff, Emma B.; Slack, Robert J.; Smith, Claire E.; Sollis, Steven L.; Staton, Hugo; Journal of Medicinal Chemistry; vol. 56; nb. 5; (2013); p. 1946 - 1960, View in Reaxys

1{2}

Bryan, Marian C.; Hein, Christopher D.; Gao, Hua; Xia, Xiaoyang; Eastwood, Heather; Bruenner, Bernd A.; Louie, Steven W.; Doherty, Elizabeth M.; ACS Combinatorial Science; vol. 15; nb. 9; (2013); p. 503 511, View in Reaxys

X-1

Patent; FUJIFILM Corporation; EP2460799; (2012); (A1) English, View in Reaxys

Chen, Xinzhi; Zhou, Shaodong; Qian, Chao; He, Chaohong; Research on Chemical Intermediates; vol. 38; nb. 7; (2012); p. 1619 - 1628, View in Reaxys

10b

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4.31

Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; DAHMANN, Georg; FIEGEN, Dennis; HANDSCHUH, Sandra; KLICIC, Jasna; LINZ, Guenter; SCHAENZLE, Gerhard; SCHNAPP, Andreas; EAST, Stephen P.; MAZANETZ, Michael Philip; SCOTT, John; WALKER, Edward; WO2011/92128; (2011); (A1) English, View in Reaxys

1, R1=2-CN

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Sato, Ippei; Morihira, Koichiro; Inami, Hiroshi; Kubota, Hirokazu; Morokata, Tatsuaki; Suzuki, Keiko; Iura, Yosuke; Nitta, Aiko; Imaoka, Takayuki; Takahashi, Toshiya; Takeuchi, Makoto; Ohta, Mitsuaki; Tsukamoto, Shin-ichi; Bioorganic and Medicinal Chemistry; vol. 16; nb. 18; (2008); p. 8607 - 8618, View in Reaxys

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10c

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substrate to XIIIa

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table 2, line 4

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sub., Tab.1, entry 3

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educt to 4/9

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tab. 1,entry 6,fluo- Grecian, Scott A.; Hadida, Sabine; Warren, Stephen D.; Tetrahedron Letters; vol. 46; nb. 27; (2005); p. ride 4683 - 4685, View in Reaxys 10

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2-FC6H4CN

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4 (R=H)

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2-CN-C6H4F

Varala, Ravi; Ramu; Alam, M. Mujahid; Adapa, Srinivas R.; Synlett; nb. 10; (2004); p. 1747 - 1750, View in Reaxys

2-F-PhCN

Voronkov, Michael V.; Gontcharov, Alexander V.; Wang, Zhi-Min; Richardson, Paul F.; Kolb, Hartmuth C.; Tetrahedron; vol. 60; nb. 41; (2004); p. 9043 - 9048, View in Reaxys

175

Patent; Neurogen Corporation; US6723743; (2004); (B1) English, View in Reaxys

9 (R1=2-F)

Claiborne, Christopher F.; McCauley, John A.; Libby, Brian E.; Curtis, Neil R.; Diggle, Helen J.; Kulagowski, Janusz J.; Michelson, Stuart R.; Anderson, Kenneth D.; Claremon, David A.; Freidinger, Roger M.; Bednar, Rodney A.; Mosser, Scott D.; Gaul, Stanley L.; Connolly, Thomas M.; Condra, Cindra L.; Bednar, Bohumil; Stump, Gary L.; Lynch, Joseph J.; Macaulay, Alison; Wafford, Keith A.; Koblan, Kenneth S.; Liverton, Nigel J.; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 4; (2003); p. 697 700, View in Reaxys

substrate, tab 2 row 3

Rogers, John F.; Green, Daniel M.; Tetrahedron Letters; vol. 43; nb. 19; (2002); p. 3585 - 3587, View in Reaxys

Sub., Table, run 12

Takamizawa; Wakasa; Fuchikami; Synlett; nb. 10; (2001); p. 1623 - 1625, View in Reaxys

Table 1, RCN row 15

Merchant, Kevin J.; Tetrahedron Letters; vol. 41; nb. 19; (2000); p. 3747 - 3749, View in Reaxys

precursor of 3a

Brown; Foubister; Ratcliffe; Tetrahedron Letters; vol. 40; nb. 6; (1999); p. 1219 - 1222, View in Reaxys

Suzuki, Tomoo; Oka, Mitsuru; Maeda, Kouji; Furusawa, Kenichi; Uesaka, Hiroshi; Kataoka, Tadashi; Chemical and Pharmaceutical Bulletin; vol. 47; nb. 1; (1999); p. 28 - 36, View in Reaxys

Table 1, entry 6

Woiwode, Thomas F.; Rose, Christoph; Wandless, Thomas J.; Journal of Organic Chemistry; vol. 63; nb. 25; (1998); p. 9594 - 9596, View in Reaxys

Patent-Specific Data (16) Prophetic ComLocation in Patent References pound Patent; Nanjing University of Science and Technology; Zou, Xiaoyuan; Wang, Na'na; Li, Feng; (10 pag.); CN104744288; (2017); (B) Chinese, View in Reaxys Patent; Zhejiang University of Technology; Zhang Guofu; Xie Xiaoqiang; Ding Chengrong; Xing Yunzhe; (6 pag.); CN106748860; (2017); (A) Chinese, View in Reaxys Patent; Yichun; Zhu, Qiming; Yuan, Qinghe; Chen, Ye; (18 pag.); CN105541702; (2016); (A) Chinese, View in Reaxys Patent; Nanjing University of Technology; Guo, Cheng; Gong, Xubin; Wu, Lou; Li, Qing; Wang, Jianjiang; (11 pag.); CN105777579; (2016); (A) Chinese, View in Reaxys Page/Page column

Patent; Woltering, Thomas; US2013/12494; (2013); (A1) English, View in Reaxys; Patent; H. Lundbeck A/S; Khanzhin, Nikolay; Simonsen, Klaus Bæk; Nielsen, Søren Møller; Juhl, Karsten; US2013/190499; (2013); (A1) English, View in Reaxys Patent; Nippon Soda Co., Ltd.; US2012/289702; (2012); (A1) English, View in Reaxys Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; DAHMANN, Georg; FIEGEN, Dennis; HANDSCHUH, Sandra; KLICIC, Jasna; LINZ, Guenter; SCHAENZLE, Gerhard; SCHNAPP, Andreas; EAST, Stephen P.; MAZANETZ, Michael Philip; SCOTT, John; WALKER, Edward; WO2011/92128; (2011); (A1) English, View in Reaxys Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1555257; (2005); (A1) English, View in Reaxys

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Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/14602; (2005); (A1) English, View in Reaxys Patent; Bayer Chemicals AG; EP1389608; (2004); (A1) German, View in Reaxys Patent; Coleman, Darrell Stephen; Jagdmann, Gunnar Erik; Johnson, Kirk Willis; Johnson, Michael Parvin; Large, Thomas Hallett; Monn, James Allen; Schoepp, Darryle Darwin; Barda, David Anthony; Britton, Thomas Charles; Dressman, Bruce Anthony; Henry, Steven Scott; Hornback, William Joseph; Tizzano, Joseph Patrick; Fichtner, Michael William; US2004/6114; (2004); (A1) English, View in Reaxys Patent; Nippon Shokubai Co., Ltd.; US6392084; (2002); (B1) English, View in Reaxys Patent; Merck and Co., Inc.; US6339090; (2002); (B1) English, View in Reaxys Patent; Pfizer Limited; PFIZER INC.; EP1184372; (2002); (A1) English, View in Reaxys prophetic product

prophetic product

Patent; Sandoz, Inc.; US4113727; (1978); (A1) English, View in Reaxys; Patent; Mitsui Chemicals, Inc.; US6242654; (2001); (B1) English, View in Reaxys; Patent; MALLINCKRODT SPECIALTY CHEMICALS COMPANY; EP253838; (1991); (B1) English, View in Reaxys; Patent; MALLINCKRODT SPECIALTY CHEMICALS COMPANY; EP253837; (1991); (B1) English, View in Reaxys; Patent; Mallinckrodt, Inc.; US4849552; (1989); (A1) English, View in Reaxys; Patent; MALLINCKRODT SPECIALTY CHEMICALS COMPANY; EP252964; (1991); (B1) English, View in Reaxys Claim

Patent; ENICHEM SYNTHESIS S.p.A.; EP441004; (1991); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.906

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

23.79

Lipinski Number

Veber Number

Boiling Point (5) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

62 - 64.5

2.5

Rosevear, Judi; Wilshire, John F. K.; Australian Journal of Chemistry; vol. 44; nb. 8; (1991); p. 1097 - 1114, View in Reaxys

90 - 92

Spagnolo et al.; Journal of the Chemical Society [Section] B: Physical Organic; (1971); p. 2006, View in Reaxys

88 - 90

Ishikawa; Inoue; Yuki Gosei Kagaku Kyokaishi; vol. 27; (1969); p. 993,996; Chem.Abstr.; vol. 72; nb. 21417, View in Reaxys

103

Finger et al.; Chemical Communications (London); (1965); p. 430,431, View in Reaxys

Borsche; Wagner-Roemmich; Justus Liebigs Annalen der Chemie; vol. 546; (1941); p. 273,275, View in Reaxys

Density (1) 1 of 1

Density [g·cm-3]

1.1335

Measurement Temperature [°C]

24.99

Liu, Hongli; Kido, Satoko; Kamiyama, Tadashi; Fujisawa, Masao; Kimura, Takayoshi; Journal of Thermal Analysis and Calorimetry; vol. 102; nb. 3; (2010); p. 1123 - 1133, View in Reaxys Association (MCS) (2) 1 of 2

Description (Association Enthalpy of association (MCS)) Temperature (Association (MCS)) [°C]

24.99

Partner (Association (MCS))

m-Fluorobenzonitrile

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Liu, Hongli; Kido, Satoko; Kamiyama, Tadashi; Fujisawa, Masao; Kimura, Takayoshi; Journal of Thermal Analysis and Calorimetry; vol. 102; nb. 3; (2010); p. 1123 - 1133, View in Reaxys 2 of 2

Description (Association Further physical properties of the complex (MCS)) Partner (Association (MCS))

1.4-dibromobenzene

Asahi, Yoshinori; Hirota, Noboru; Bulletin of the Chemical Society of Japan; vol. 55; nb. 5; (1982); p. 1379 - 1386, View in Reaxys; Nagaoka, Shin-ichi; Harrigan, Edward T.; Noda, Masayo; Hirota, Noboru; Higuchi, Jiro; Bulletin of the Chemical Society of Japan; vol. 59; nb. 2; (1986); p. 355 - 362, View in Reaxys Chromatographic Data (2) Chromatographic Original string data

Location

References

GC (Gas chroma- GCMS analysis, Page/Page coltography) where the product umn 36 peak was observed at 7.10 min.

Patent; DOW AGROSCIENCES LLC; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; SANFORD, Melanie; RYAN, Sarah; SCHIMLER, Sydonie; CHENG, Yang; BLAND, Douglas; (47 pag.); WO2017/24167; (2017); (A1) English, View in Reaxys

GC (Gas chromatography)

supporting information

Nagaki, Aiichiro; Uesugi, Yuki; Kim, Heejin; Yoshida, Jun-Ichi; Chemistry - An Asian Journal; vol. 8; nb. 4; (2013); p. 705 - 708, View in Reaxys; Kiss, Arpad; Hell, Zoltan; Synthetic Communications; vol. 43; nb. 13; (2013); p. 1778 - 1786, View in Reaxys

Crystal Property Description (3) Colour & Other Location Properties

References

colourless

supporting information

colourless

Xi, Guoqin; Han, Xiuling; Lu, Xiyan; Advanced Synthesis and Catalysis; vol. 354; nb. 14-15; (2012); p. 2701 - 2705,5, View in Reaxys; Feng, Qiang; Song, Qiuling; Advanced Synthesis and Catalysis; vol. 356; nb. 8; (2014); p. 1697 - 1702, View in Reaxys; Qi, Chaorong; Hu, Xiaohan; He, Haitao; Synlett; vol. 27; nb. 13; (2016); p. 1979 - 1982; Art.No: ST-2016-W0122-L, View in Reaxys; Shi, Shicheng; Szostak, Michal; Organic Letters; vol. 19; nb. 12; (2017); p. 3095 - 3098, View in Reaxys Xu, Zhicheng; Xiao, Yunqing; Ding, Hong; Cao, Changsheng; Li, Haitao; Pang, Guangsheng; Shi, Yanhui; Synthesis (Germany); vol. 47; nb. 11; (2015); p. 1560 1566; Art.No: SS-2014-F0771-OP, View in Reaxys

yellow

supporting information

Kiss, Arpad; Hell, Zoltan; Synthetic Communications; vol. 43; nb. 13; (2013); p. 1778 1786, View in Reaxys

Electrochemical Behaviour (1) Description (Elec- References trochemical Behaviour) Electrochemical properties

Houser et al.; Journal of the American Chemical Society; vol. 95; (1973); p. 6033,6034,6035, View in Reaxys

Electrochemical Characteristics (1) 1 of 1

Description (Electrochemical Characteristics)

cyclovoltammetry

Solvent (Electrochemical Characteristics)

N,N-dimethyl-formamide

Temperature (Electrochemical Characteristics) [°C]

21.84

Location

supporting information

Comment (Electrochem- Saturated calomel electrode (SCE); potential diagram; 0.1 M Et4NClO4 ical Characteristics) Peshkov, Roman Yu.; Panteleeva, Elena V.; Shchegoleva, Lyudmila N.; Bagryanskaya, Irina Yu.; Rybalova, Tatyana V.; Vasilieva, Nadezhda V.; Shteingarts, Vitalij D.; European Journal of Organic Chemistry; vol. 2015; nb. 20; (2015); p. 4524 - 4531, View in Reaxys Enthalpy of Combustion (1)

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Comment (Enthalpy of Combustion)

References

Enthalpy of combustion given

Ribeiro Da Silva, Manuel A. V.; Monte, Manuel J. S.; Rocha, Ines M.; Cimas, Alvaro; Journal of Organic Chemistry; vol. 77; nb. 9; (2012); p. 4312 - 4322, View in Reaxys

Enthalpy of Formation (1) Comment (EnReferences thalpy of Formation) Enthalpy of formation given

Ribeiro Da Silva, Manuel A. V.; Monte, Manuel J. S.; Rocha, Ines M.; Cimas, Alvaro; Journal of Organic Chemistry; vol. 77; nb. 9; (2012); p. 4312 - 4322, View in Reaxys

Further Information (2) Description (Fur- References ther Information) Further information

Roark; Smith; Journal of Physical Chemistry; vol. 73; (1969); p. 1046, View in Reaxys

Further information

Finger et al.; Chemical Communications (London); (1965); p. 430,431, View in Reaxys

Molecular Deformation (1) Description (MoReferences lecular Deformation) Force constants

Kumar; Rao; Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy; vol. 53 A; nb. 12; (1997); p. 2023 - 2032, View in Reaxys

Vapour Pressure (6) Vapour Pressure Temperature (Va[Torr] pour Pressure) [°C]

Location

References

0.238749

13.84

supporting information

Ribeiro Da Silva, Manuel A. V.; Monte, Manuel J. S.; Rocha, Ines M.; Cimas, Alvaro; Journal of Organic Chemistry; vol. 77; nb. 9; (2012); p. 4312 - 4322, View in Reaxys

0.277678

15.85

supporting information

Ribeiro Da Silva, Manuel A. V.; Monte, Manuel J. S.; Rocha, Ines M.; Cimas, Alvaro; Journal of Organic Chemistry; vol. 77; nb. 9; (2012); p. 4312 - 4322, View in Reaxys

0.322232

17.84

supporting information

Ribeiro Da Silva, Manuel A. V.; Monte, Manuel J. S.; Rocha, Ines M.; Cimas, Alvaro; Journal of Organic Chemistry; vol. 77; nb. 9; (2012); p. 4312 - 4322, View in Reaxys

0.373087

19.85

supporting information

Ribeiro Da Silva, Manuel A. V.; Monte, Manuel J. S.; Rocha, Ines M.; Cimas, Alvaro; Journal of Organic Chemistry; vol. 77; nb. 9; (2012); p. 4312 - 4322, View in Reaxys

0.430918

21.82

supporting information

Ribeiro Da Silva, Manuel A. V.; Monte, Manuel J. S.; Rocha, Ines M.; Cimas, Alvaro; Journal of Organic Chemistry; vol. 77; nb. 9; (2012); p. 4312 - 4322, View in Reaxys

0.49625

23.83

supporting information

Ribeiro Da Silva, Manuel A. V.; Monte, Manuel J. S.; Rocha, Ines M.; Cimas, Alvaro; Journal of Organic Chemistry; vol. 77; nb. 9; (2012); p. 4312 - 4322, View in Reaxys

NMR Spectroscopy (25) 1 of 25

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Location

supporting information

Niu, Baoqiang; Lu, Fei; Zhang, Hong-Yu; Zhang, Yuecheng; Zhao, Jiquan; Chemistry Letters; vol. 46; nb. 3; (2017); p. 330 - 333, View in Reaxys

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2 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

19F

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Shi, Shicheng; Szostak, Michal; Organic Letters; vol. 19; nb. 12; (2017); p. 3095 - 3098, View in Reaxys 4 of 25

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

19F

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Shi, Shicheng; Szostak, Michal; Organic Letters; vol. 19; nb. 12; (2017); p. 3095 - 3098, View in Reaxys 5 of 25

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

19F

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

471

Location

supporting information

Shi, Shicheng; Szostak, Michal; Organic Letters; vol. 19; nb. 12; (2017); p. 3095 - 3098, View in Reaxys 6 of 25

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Feng, Qiang; Song, Qiuling; Advanced Synthesis and Catalysis; vol. 356; nb. 8; (2014); p. 1697 - 1702, View in Reaxys; Xu, Zhicheng; Xiao, Yunqing; Ding, Hong; Cao, Changsheng; Li, Haitao; Pang, Guangsheng; Shi, Yanhui; Synthesis (Germany); vol. 47; nb. 11; (2015); p. 1560 - 1566; Art.No: SS-2014-F0771-OP,

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View in Reaxys; Qi, Chaorong; Hu, Xiaohan; He, Haitao; Synlett; vol. 27; nb. 13; (2016); p. 1979 - 1982; Art.No: ST-2016-W0122-L, View in Reaxys 7 of 25

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

19F

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Qi, Chaorong; Hu, Xiaohan; He, Haitao; Synlett; vol. 27; nb. 13; (2016); p. 1979 - 1982; Art.No: ST-2016-W0122L, View in Reaxys 8 of 25

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

19F

Solvents (NMR Spectro- dichloromethane-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

377

Location

supporting information

Ryan, Sarah J.; Schimler, Sydonie D.; Bland, Douglas C.; Sanford, Melanie S.; Organic Letters; vol. 17; nb. 8; (2015); p. 1866 - 1869, View in Reaxys 10 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Kiss, Arpad; Hell, Zoltan; Synthetic Communications; vol. 43; nb. 13; (2013); p. 1778 - 1786, View in Reaxys 11 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

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Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Kiss, Arpad; Hell, Zoltan; Synthetic Communications; vol. 43; nb. 13; (2013); p. 1778 - 1786, View in Reaxys 12 of 25

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Rajender Reddy; Uma Maheswari; Venkateshwar; Prashanthi; Lakshmi Kantam; Tetrahedron Letters; vol. 50; nb. 18; (2009); p. 2050 - 2053, View in Reaxys 13 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

19F

Gutowsky et al.; Journal of the American Chemical Society; vol. 74; (1952); p. 4809,4811, View in Reaxys; Sun, Haoran; DiMagno, Stephen G.; Angewandte Chemie - International Edition; vol. 45; nb. 17; (2006); p. 2720 - 2725, View in Reaxys 14 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Lauterbur; Annals of the New York Academy of Sciences; vol. 70; (1958); p. 841,853, View in Reaxys; Sun, Haoran; DiMagno, Stephen G.; Angewandte Chemie - International Edition; vol. 45; nb. 17; (2006); p. 2720 - 2725, View in Reaxys 15 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Sun, Haoran; DiMagno, Stephen G.; Angewandte Chemie - International Edition; vol. 45; nb. 17; (2006); p. 2720 2725, View in Reaxys 16 of 25

Nucleus (NMR Spectroscopy)

13C

Coupling Nuclei

19F

Sun, Haoran; DiMagno, Stephen G.; Angewandte Chemie - International Edition; vol. 45; nb. 17; (2006); p. 2720 2725, View in Reaxys 17 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

Zecek, Petr; Dransfeld, Alk; Exner, Otto; Schraml, Jan; Magnetic Resonance in Chemistry; vol. 44; nb. 12; (2006); p. 1073 - 1080, View in Reaxys

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18 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Rae, Ian D.; Weigold, Josephine A.; De Kowalewski, Dora G.; Biekofsky, Rodolfo R.; Contreras, Ruben H.; Magnetic Resonance in Chemistry; vol. 34; nb. 3; (1996); p. 181 - 184, View in Reaxys 19 of 25

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

19F-13C.

Rae, Ian D.; Weigold, Josephine A.; De Kowalewski, Dora G.; Biekofsky, Rodolfo R.; Contreras, Ruben H.; Magnetic Resonance in Chemistry; vol. 34; nb. 3; (1996); p. 181 - 184, View in Reaxys 20 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

19F

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Fifolt, Michael J.; Sojka, Stanley A.; Wolfe, Roger A.; Hojnicki, Daniel S.; Bieron, Joseph F.; Dinan, Frank J.; Journal of Organic Chemistry; vol. 54; nb. 13; (1989); p. 3019 - 3023, View in Reaxys 21 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

19F

Solvents (NMR Spectro- acetone-d6 scopy) Fifolt, Michael J.; Sojka, Stanley A.; Wolfe, Roger A.; Hojnicki, Daniel S.; Bieron, Joseph F.; Dinan, Frank J.; Journal of Organic Chemistry; vol. 54; nb. 13; (1989); p. 3019 - 3023, View in Reaxys 22 of 25

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

19F

Solvents (NMR Spectro- CHCl3 scopy) Zweig, Arnold; Fischer, Robert G.; Lancaster, John E.; Journal of Organic Chemistry; vol. 45; nb. 18; (1980); p. 3597 - 3603, View in Reaxys 23 of 25

Description (NMR Spec- NMR troscopy) Foust; Ford; Journal of the American Chemical Society; vol. 94; (1972); p. 5686,5688, View in Reaxys; Singh; Singh; Journal of Magnetic Resonance (1969-1992); vol. 16; (1974); p. 110,114, View in Reaxys

24 of 25

Description (NMR Spec- Chemical shifts troscopy) Comment (NMR Spectroscopy)

13C-NMR chem. shifts

Smith; Deavenport; Journal of Magnetic Resonance (1969-1992); vol. 7; (1972); p. 364, View in Reaxys 25 of 25

Description (NMR Spec- Chemical shifts troscopy) Roark; Smith; Journal of Physical Chemistry; vol. 73; (1969); p. 1046, View in Reaxys

IR Spectroscopy (6)

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1 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

Qi, Chaorong; Hu, Xiaohan; He, Haitao; Synlett; vol. 27; nb. 13; (2016); p. 1979 - 1982; Art.No: ST-2016-W0122L, View in Reaxys 2 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3120 - 455 cm**(-1)

Kumar; Rao; Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy; vol. 53 A; nb. 12; (1997); p. 2023 - 2032, View in Reaxys 4 of 6

Description (IR Spectroscopy)

Deady et al.; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 31; (1975); p. 1671,1672, View in Reaxys; Green; Harrison; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 32; (1976); p. 1279,1284,1285, View in Reaxys 5 of 6

Description (IR Spectroscopy)

Bands

Deady et al.; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 31; (1975); p. 1671,1672, View in Reaxys 6 of 6

Description (IR Spectroscopy)

Spectrum

Katritzky et al.; Journal of the American Chemical Society; vol. 91; (1969); p. 628, View in Reaxys Mass Spectrometry (5) Description (Mass Location Spectrometry)

Comment (Mass Spectrometry)

References

gas chromatogra- supporting inforphy mass specmation trometry (GCMS); spectrum

Kiss, Arpad; Hell, Zoltan; Synthetic Communications; vol. 43; nb. 13; (2013); p. 1778 - 1786, View in Reaxys; Schimler, Sydonie D.; Cismesia, Megan A.; Hanley, Patrick S.; Froese, Robert D.J.; Jansma, Matthew J.; Bland, Douglas C.; Sanford, Melanie S.; Journal of the American Chemical Society; vol. 139; nb. 4; (2017); p. 1452 - 1455, View in Reaxys

electron impact (EI); spectrum

Qi, Chaorong; Hu, Xiaohan; He, Haitao; Synlett; vol. 27; nb. 13; (2016); p. 1979 - 1982; Art.No: ST-2016-W0122-L, View in Reaxys

supporting information

gas chromatography mass spectrometry (GCMS); spectrum Spectrum

GCMS (Gas chromatography mass spectrometry)

mol peak

Rajender Reddy; Uma Maheswari; Venkateshwar; Prashanthi; Lakshmi Kantam; Tetrahedron Letters; vol. 50; nb. 18; (2009); p. 2050 - 2053, View in Reaxys

Molecular peak

Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1555257; (2005); (A1) English, View in Reaxys

UV/VIS Spectroscopy (3)

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1 of 3

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

dichloromethane

Ribeiro Da Silva, Manuel A. V.; Monte, Manuel J. S.; Rocha, Ines M.; Cimas, Alvaro; Journal of Organic Chemistry; vol. 77; nb. 9; (2012); p. 4312 - 4322, View in Reaxys 2 of 3

Description (UV/VIS Spectroscopy)

Spectrum

Findley et al.; Journal of the American Chemical Society; vol. 101; (1979); p. 4511,4514, View in Reaxys; Lui; McGlynn; Journal of Luminescence; vol. 9; (1974); p. 449,450,454,455, View in Reaxys 3 of 3

Description (UV/VIS Spectroscopy)

UV/VIS

Hill et al.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1977); p. 1262,1266, View in Reaxys; Carsey et al.; Journal of the American Chemical Society; vol. 101; (1979); p. 4502,4505-4506, View in Reaxys; Singh; Indian Journal of Physics (1926-1976); vol. 42; (1968); p. 571, View in Reaxys ESR Spectroscopy (4) 1 of 4

Description (ESR Spectroscopy)

Signals

Solvents (ESR Spectroscopy)

ethanol

Temperature (ESR Spectroscopy) [°C]

-196.2

Wagner, Peter J.; May, Mary L.; Journal of Physical Chemistry; vol. 95; nb. 25; (1991); p. 10317 - 10321, View in Reaxys 2 of 4

Description (ESR Spectroscopy)

ESR-hyperfine coupling constants

Comment (ESR Spectroscopy)

1H, 19F.

Asahi, Yoshinori; Hirota, Noboru; Bulletin of the Chemical Society of Japan; vol. 55; nb. 5; (1982); p. 1379 - 1386, View in Reaxys 3 of 4

Description (ESR Spectroscopy)

Signals

Asahi, Yoshinori; Hirota, Noboru; Bulletin of the Chemical Society of Japan; vol. 55; nb. 5; (1982); p. 1379 - 1386, View in Reaxys 4 of 4

Description (ESR Spectroscopy)

ESR

Buick et al.; Journal of the Chemical Society [Section] A: Inorganic, Physical, Theoretical; (1969); p. 666, View in Reaxys; Greatorex et al.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1973); p. 1762,1764, View in Reaxys; Wagner; May; Chemical Physics Letters; vol. 39; (1976); p. 350, View in Reaxys Raman Spectroscopy (2) Description (Ram- References an Spectroscopy) Bands

Kumar; Rao; Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy; vol. 53 A; nb. 12; (1997); p. 2023 - 2032, View in Reaxys

Raman

Green; Harrison; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 32; (1976); p. 1279,1284,1285, View in Reaxys

Luminescence Spectroscopy (2) Description (LuReferences minescence Spectroscopy) Luminescence lifetime

Carsey et al.; Journal of the American Chemical Society; vol. 101; (1979); p. 4502,4505-4506, View in Reaxys; Lui; McGlynn; Journal of Luminescence; vol. 9; (1974); p. 449,450,454,455, View in Reaxys

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Luminescence

Findley et al.; Journal of the American Chemical Society; vol. 101; (1979); p. 4511,4514, View in Reaxys; Lui; McGlynn; Journal of Luminescence; vol. 9; (1974); p. 449,450,454,455, View in Reaxys

Fluorescence Spectroscopy (1) Description (Fluo- References rescence Spectroscopy) Fluorescence

Carsey et al.; Journal of the American Chemical Society; vol. 101; (1979); p. 4502,4505-4506, View in Reaxys

Phosphorescence Spectroscopy (1) Description References (Phosphorescence Spectroscopy) Phosphorescence Carsey et al.; Journal of the American Chemical Society; vol. 101; (1979); p. 4502,4505-4506, View in Reaxys Other Spectroscopic Methods (1) Description (Oth- References er Spectroscopic Methods) Photoelectron spectrum

Palmer, Michael H.; Moyes, William; Spiers, Martin; Journal of Molecular Structure; vol. 62; (1980); p. 165 - 188, View in Reaxys

Use (1) Use Pattern

References

Intermediates for Patent; Nippon Shokubai Co., Ltd.; US6392084; (2002); (B1) English, View in Reaxys the synthesis of agricultural chemicals, medicines, and dyes Medchem (1) 1 of 1

Target Mutant/Chimera Details

Indoleamine 2,3-dioxygenase 1 [Human]:Wild

Substance Action on Target

Inhibitor

Target Species (Bioactivity)

Human

Target Subunit Proteins

Indoleamine 2,3-dioxygenase 1 [Human]

Target Transfection

Transfected

Bioassay Category

In Vitro (Efficacy)

Biological Species/NCBI Escherichia coli M15 ID Substance RN

2042184View in Reaxys

Substance Dose

50 - 100 nM

Measurement Parameter

IC50

Unit

Quantitative value

Measurement pX

7.25

Target, Subunit, Species Indoleamine 2,3-dioxygenase 1 [Human]

Reaxys ID 6858373 View in Reaxys

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Chemical Name: [18F]-2-fluorobenzonitrile Linear Structure Formula: C7H4 (18)FN Molecular Formula: C7H4FN Molecular Weight: 120.115 Type of Substance: isocyclic InChI Key: GDHXJNRAJRCGMX-COJKEBBMSA-N Note:

18F

Substance Label (1) Label References <2-18F>C6H4CN

Attina, Marina; Cacace, Fulvio; Wolf, A. P.; Journal of the Chemical Society, Chemical Communications; nb. 3; (1983); p. 108 - 109, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.906

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

23.79

Lipinski Number

Veber Number

Chromatographic Data (1) Chromatographic References data HPLC (High performance liquid chromatography)

Chun, Joong-Hyun; Telu, Sanjay; Lu, Shuiyu; Pike, Victor W.; Organic and Biomolecular Chemistry; vol. 11; nb. 31; (2013); p. 5094 - 5099, View in Reaxys

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