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1 substances in Reaxys
2017-10-25 10h:19m:40s (EST)
O
1. Query O
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Reaxys ID 4920 View in Reaxys
I
1/1 CAS Registry Number: 5876-51-7 Chemical Name: 5-iodo-1,3-benzodioxole; 4-iodo-1,2-methylenedioxybenzene; 1-iodo-3,4-(methylenedioxy)benzene; 3,4(methylenedioxy)-1-iodobenzene; 3,4-(methylenedioxy)phenyl iodide; 1-iodo-3,4-methylenedioxybenzene; 3,4-methylenedioxy iodobenzene Linear Structure Formula: (CH2(O)2)(C6H3)I Molecular Formula: C7H5IO2 Molecular Weight: 248.02 Type of Substance: heterocyclic InChI Key: NMMCBIXYIYQHCP-UHFFFAOYSA-N Note:
O O
Substance Label (29) Label References 2
Lee, Changwook; Park, Hye-Kyung; Jeong, Hanbin; Lim, Jaehwa; Lee, An-Jung; Cheon, Keun Young; Kim, Chul-Su; Thomas, Ajesh P.; Bae, Boram; Kim, Nam Doo; Kim, Seong Heon; Suh, Pann-Ghill; Ryu, Ja-Hyoung; Kang, Byoung Heon; Journal of the American Chemical Society; vol. 137; nb. 13; (2015); p. 4358 - 4367, View in Reaxys; Ye, Shengqing; Yang, Weibo; Coon, Timothy; Fanning, Dewey; Neubert, Tim; Stamos, Dean; Yu, Jin-Quan; Chemistry - A European Journal; vol. 22; nb. 14; (2016); p. 4748 - 4752, View in Reaxys; Komeyama, Kimihiro; Ohata, Ryo; Kiguchi, Shinnosuke; Osaka, Itaru; Chemical Communications; vol. 53; nb. 48; (2017); p. 6401 - 6404, View in Reaxys
4
Xia, Shanghua; Gan, Lu; Wang, Kailiang; Li, Zheng; Ma, Dawei; Journal of the American Chemical Society; vol. 138; nb. 41; (2016); p. 13493 - 13496, View in Reaxys; Gao, Jie; Bhunia, Subhajit; Wang, Kailiang; Gan, Lu; Xia, Shanghua; Ma, Dawei; Organic Letters; vol. 19; nb. 11; (2017); p. 2809 - 2812, View in Reaxys
10
Xu, Bin; Gartman, Jackson A.; Tambar, Uttam K.; Tetrahedron; vol. 73; nb. 29; (2017); p. 4150 - 4159, View in Reaxys
1e
Komeyama, Kimihiro; Kiguchi, Shinnosuke; Takaki, Ken; Chemical Communications; vol. 52; nb. 43; (2016); p. 7009 - 7012, View in Reaxys
6g
Suchand, Basuli; Satyanarayana, Gedu; Journal of Organic Chemistry; vol. 81; nb. 15; (2016); p. 6409 6423, View in Reaxys
SI-14
Faizi, Darius J.; Davis, Ashlee J.; Meany, Fiach B.; Blum, Suzanne A.; Angewandte Chemie - International Edition; vol. 55; nb. 46; (2016); p. 14286 - 14290; Angew. Chem.; vol. 128; nb. 46; (2016); p. 14498 14502,5, View in Reaxys
2y
Lu, Ju-You; Wan, Hong; Zhang, Jianwei; Wang, Zhixuan; Li, Yang; Du, Yongmei; Li, Chunying; Liu, Zhao-Tie; Liu, Zhong-Wen; Lu, Jian; Chemistry - A European Journal; vol. 22; nb. 49; (2016); p. 17542 17546, View in Reaxys
2m
Chen, Mao; Ichikawa, Saki; Buchwald, Stephen L.; Angewandte Chemie - International Edition; vol. 54; nb. 1; (2015); p. 263 - 266; Angew. Chem.; vol. 127; nb. 01; (2015); p. 265 - 268,4, View in Reaxys; Chen, Hu; Lei, Min; Hu, Lihong; Tetrahedron; vol. 70; nb. 35; (2014); p. 5626 - 5631, View in Reaxys
8b
Guo, Lei; Zhang, Fengying; Hu, Weimin; Li, Lei; Jia, Yanxing; Chemical Communications; vol. 50; nb. 25; (2014); p. 3299 - 3302, View in Reaxys
9
Sun, Chunrui; Potter, Bowman; Morken, James P.; Journal of the American Chemical Society; vol. 136; nb. 18; (2014); p. 6534 - 6537, View in Reaxys
104
Gutekunst, Will R.; Baran, Phil S.; Journal of Organic Chemistry; vol. 79; nb. 6; (2014); p. 2430 - 2452, View in Reaxys
S4
Kocsis, Laura S.; Brummond, Kay M.; Organic Letters; vol. 16; nb. 16; (2014); p. 4158 - 4161, View in Reaxys
12b
Ma, Ran; Huang, Cheng-Bin; Liu, An-Hua; Li, Xue-Dong; He, Liang-Nian; Catalysis Science and Technology; vol. 4; nb. 12; (2014); p. 4308 - 4312, View in Reaxys
14
Shu, Lianhe; Wang, Ping; Radinov, Roumen; Dominique, Romyr; Wright, James; Alabanza, Lady Mae; Dong, Yan; Organic Process Research and Development; vol. 17; nb. 1; (2013); p. 114 - 119, View in Reaxys
1
Yapuri, Umanadh; Palle, Sadanandam; Gudaparthi, Omprakash; Narahari, Srinivasa Reddy; Rawat, Dhwajbahadur K.; Mukkanti, Khagga; Vantikommu, Jyothi; Tetrahedron Letters; vol. 54; nb. 35; (2013); p. 4732 - 4734, View in Reaxys
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1n
Komeyama, Kimihiro; Kashihara, Tetsuya; Takaki, Ken; Tetrahedron Letters; vol. 54; nb. 42; (2013); p. 5659 - 5662, View in Reaxys
7b
Parella, Ramarao; Gopalakrishnan, Bojan; Babu, Srinivasarao Arulananda; Journal of Organic Chemistry; vol. 78; nb. 23; (2013); p. 11911 - 11934, View in Reaxys
3w
Groll, Klaus; Bluemke, Tobias D.; Unsinn, Andreas; Haas, Diana; Knochel, Paul; Angewandte Chemie, International Edition; vol. 51; nb. 44; (2012); p. 11157 - 11161,5; Angewandte Chemie; vol. 124; nb. 44; (2012); p. 11319 - 11323,5, View in Reaxys
5
He, Huazhong; Zatorska, Danuta; Kim, Joungnam; Aguirre, Julia; Llauger, Laura; She, Yuhong; Wu, Nian; Immormino, Robert M.; Gewirth, Daniel T.; Chiosis, Gabriela; Journal of Medicinal Chemistry; vol. 49; nb. 1; (2006); p. 381 - 390, View in Reaxys
43
Patent; EURO-CELTIQUE S.A.; WO2005/56524; (2005); (A2) English, View in Reaxys
3c', table 1
Yadav; Reddy; Basak; Narsaiah; Advanced Synthesis and Catalysis; vol. 346; nb. 1; (2004); p. 77 - 82, View in Reaxys
7
Mirk, Daniela; Willner, Alexander; Froehlich, Roland; Waldvogel, Siegfried R.; Advanced Synthesis and Catalysis; vol. 346; nb. 6; (2004); p. 675 - 681, View in Reaxys
Tab.1. run 6, pprod.
Krishna Mohan; Narender; Kulkarni; Tetrahedron Letters; vol. 45; nb. 43; (2004); p. 8015 - 8018, View in Reaxys
18
Harrowven, David C; Nunn, Michael I.T; Fenwick, David R; Tetrahedron Letters; vol. 42; nb. 42; (2001); p. 7501 - 7502, View in Reaxys
B5
Conn, Costa; Shimmon, Ronald; Cordaro, Frank; Hargraves, Tracey-Lea; Ibrahim, Peter; Bioorganic and Medicinal Chemistry Letters; vol. 11; nb. 19; (2001); p. 2565 - 2568, View in Reaxys
1c
Garcon; Vassiliou; Cavicchioli; Hartmann; Monteiro; Balme; Journal of Organic Chemistry; vol. 66; nb. 11; (2001); p. 4069 - 4073, View in Reaxys
1i
Bottex; Cavicchioli; Hartmann; Monteiro; Balme; Journal of Organic Chemistry; vol. 66; nb. 1; (2001); p. 175 - 179, View in Reaxys
10d
Witulski, Bernhard; Buschmann, Nicole; Bergstraesser, Uwe; Tetrahedron; vol. 56; nb. 43; (2000); p. 8473 - 8480, View in Reaxys
15
Ikeda, Masazumi; Serry; Bialy, El; Hirose, Ken-Ichi; Kotake, Miho; Sato, Tatsunori; Bayomi, Said M. M.; Shehata, Ihsan A.; Abdelal, Ali M.; Gad, Laila M.; Yakura, Takayuki; Chemical and Pharmaceutical Bulletin; vol. 47; nb. 7; (1999); p. 983 - 987, View in Reaxys
Patent-Specific Data (2) References Patent; Sun Yat-sen University; Wan Yiqian; Ding Xiaomei; Huang Manna; Zhu Xinhai; Yi Zhou; CN106883132; (2017); (A) Chinese, View in Reaxys Patent; TOYAMA CHEMICAL CO., LTD.; EP1860098; (2007); (A1) English, View in Reaxys Druglikeness (1) 1 of 1
LogP
2.579
H Bond Donors
0
H Bond Acceptors
0
Rotatable Bonds
0
TPSA
18.46
Lipinski Number
4
Veber Number
2
Boiling Point (7) Boiling Point [°C]
Pressure (Boiling Point) [Torr]
Comment (Boiling References Point)
76
1
Kurono, Nobuhito; Sugita, Kazuya; Takasugi, Shingo; Tokuda, Masao; Tetrahedron; vol. 55; nb. 19; (1999); p. 6097 - 6108, View in Reaxys
78.5 - 79
0.7
Orito; Hatakeyama; Takeo; Suginome; Synthesis; nb. 10; (1995); p. 1273 - 1277, View in Reaxys
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79 - 82
0.4
Pearson; Postich; Journal of Organic Chemistry; vol. 59; nb. 19; (1994); p. 5662 - 5671, View in Reaxys
116 - 125
10
Dallacker; Adolphen; Justus Liebigs Annalen der Chemie; vol. 691; (1966); p. 138,140, View in Reaxys
98
1
El'zow; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 2739,2762, View in Reaxys
257 - 258
Oel.
Mameli; Boi; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 15 II; (1906); p. 104; Gazzetta Chimica Italiana; vol. 36 II; (1906); p. 380, View in Reaxys
Oel.
Mameli; Boi; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 15 II; (1906); p. 104; Gazzetta Chimica Italiana; vol. 36 II; (1906); p. 380, View in Reaxys
Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]
Temperature (Refractive Index) [°C]
References
1.6335
20
El'zow; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 2739,2762, View in Reaxys
156 - 157
30
589
Density (1) 1 of 1
Density [g·cm-3]
1.959
Reference Temperature [°C]
4
Measurement Temperature [°C]
20
El'zow; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 2739,2762, View in Reaxys Chromatographic Data (1) Chromatographic References data TLC (Thin layer chromatography)
Suchand, Basuli; Satyanarayana, Gedu; Journal of Organic Chemistry; vol. 81; nb. 15; (2016); p. 6409 6423, View in Reaxys
Crystal Property Description (2) Colour & Other Location Properties
References
colourless
supporting information
Chen, Mao; Ichikawa, Saki; Buchwald, Stephen L.; Angewandte Chemie - International Edition; vol. 54; nb. 1; (2015); p. 263 - 266; Angew. Chem.; vol. 127; nb. 01; (2015); p. 265 - 268,4, View in Reaxys
brown
supporting information
Petrone, David A.; Yoon, Hyung; Weinstabl, Harald; Lautens, Mark; Angewandte Chemie - International Edition; vol. 53; nb. 30; (2014); p. 7908 - 7912; Angew. Chem.; vol. 53; nb. 30; (2014); p. 8042 - 8046,5, View in Reaxys
NMR Spectroscopy (13) 1 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Chen, Mao; Ichikawa, Saki; Buchwald, Stephen L.; Angewandte Chemie - International Edition; vol. 54; nb. 1; (2015); p. 263 - 266; Angew. Chem.; vol. 127; nb. 01; (2015); p. 265 - 268,4, View in Reaxys; Lee, Changwook; Park, Hye-Kyung; Jeong, Hanbin; Lim, Jaehwa; Lee, An-Jung; Cheon, Keun Young; Kim, Chul-Su; Thomas, Ajesh P.; Bae, Boram; Kim, Nam Doo; Kim, Seong Heon; Suh, Pann-Ghill; Ryu, Ja-Hyoung; Kang, Byoung Heon; Journal of the American Chemical Society; vol. 137; nb. 13; (2015); p. 4358 - 4367, View in Reaxys
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2 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Location
supporting information
Chen, Mao; Ichikawa, Saki; Buchwald, Stephen L.; Angewandte Chemie - International Edition; vol. 54; nb. 1; (2015); p. 263 - 266; Angew. Chem.; vol. 127; nb. 01; (2015); p. 265 - 268,4, View in Reaxys 3 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]
22.84
Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Petrone, David A.; Yoon, Hyung; Weinstabl, Harald; Lautens, Mark; Angewandte Chemie - International Edition; vol. 53; nb. 30; (2014); p. 7908 - 7912; Angew. Chem.; vol. 53; nb. 30; (2014); p. 8042 - 8046,5, View in Reaxys 4 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]
22.84
Frequency (NMR Spectroscopy) [MHz]
100
Location
supporting information
Petrone, David A.; Yoon, Hyung; Weinstabl, Harald; Lautens, Mark; Angewandte Chemie - International Edition; vol. 53; nb. 30; (2014); p. 7908 - 7912; Angew. Chem.; vol. 53; nb. 30; (2014); p. 8042 - 8046,5, View in Reaxys 5 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
400
He, Huazhong; Zatorska, Danuta; Kim, Joungnam; Aguirre, Julia; Llauger, Laura; She, Yuhong; Wu, Nian; Immormino, Robert M.; Gewirth, Daniel T.; Chiosis, Gabriela; Journal of Medicinal Chemistry; vol. 49; nb. 1; (2006); p. 381 - 390, View in Reaxys 6 of 13
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
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Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
400
He, Huazhong; Zatorska, Danuta; Kim, Joungnam; Aguirre, Julia; Llauger, Laura; She, Yuhong; Wu, Nian; Immormino, Robert M.; Gewirth, Daniel T.; Chiosis, Gabriela; Journal of Medicinal Chemistry; vol. 49; nb. 1; (2006); p. 381 - 390, View in Reaxys 7 of 13
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Yadav; Reddy; Basak; Narsaiah; Advanced Synthesis and Catalysis; vol. 346; nb. 1; (2004); p. 77 - 82, View in Reaxys 8 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Yadav; Reddy; Basak; Narsaiah; Advanced Synthesis and Catalysis; vol. 346; nb. 1; (2004); p. 77 - 82, View in Reaxys 9 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Orito; Hatakeyama; Takeo; Suginome; Synthesis; nb. 10; (1995); p. 1273 - 1277, View in Reaxys 10 of 13
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)
1H-1H
Orito; Hatakeyama; Takeo; Suginome; Synthesis; nb. 10; (1995); p. 1273 - 1277, View in Reaxys 11 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Pearson; Postich; Journal of Organic Chemistry; vol. 59; nb. 19; (1994); p. 5662 - 5671, View in Reaxys 12 of 13
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Pearson; Postich; Journal of Organic Chemistry; vol. 59; nb. 19; (1994); p. 5662 - 5671, View in Reaxys 13 of 13
Description (NMR Spec- Spin-spin coupling constants troscopy)
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Comment (NMR Spectroscopy)
1H-1H
Pearson; Postich; Journal of Organic Chemistry; vol. 59; nb. 19; (1994); p. 5662 - 5671, View in Reaxys IR Spectroscopy (4) 1 of 4
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
neat liquid
Location
supporting information
Chen, Mao; Ichikawa, Saki; Buchwald, Stephen L.; Angewandte Chemie - International Edition; vol. 54; nb. 1; (2015); p. 263 - 266; Angew. Chem.; vol. 127; nb. 01; (2015); p. 265 - 268,4, View in Reaxys 2 of 4
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
neat liquid
Yadav; Reddy; Basak; Narsaiah; Advanced Synthesis and Catalysis; vol. 346; nb. 1; (2004); p. 77 - 82, View in Reaxys 3 of 4
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
neat (no solvent)
Comment (IR Spectroscopy)
2892 - 797 cm**(-1)
Pearson; Postich; Journal of Organic Chemistry; vol. 59; nb. 19; (1994); p. 5662 - 5671, View in Reaxys 4 of 4
Description (IR Spectroscopy)
Spectrum
El'zow; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 2739,2762, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) spectrum; electron impact (EI)
Yadav; Reddy; Basak; Narsaiah; Advanced Synthesis and Catalysis; vol. 346; nb. 1; (2004); p. 77 - 82, View in Reaxys
spectrum
Pearson; Postich; Journal of Organic Chemistry; vol. 59; nb. 19; (1994); p. 5662 - 5671, View in Reaxys
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