Reaxys
PubChem
eMolecules
Reactions (138)
Substances (1)
Citations (84)
Structure
Structure/Compound Data Chemical Name: 1,4-bis(2-hydroxyethoxy)benzene Reaxys Registry Number: 514873
CAS Registry Number: 104-38-1 Type of Substance: isocyclic Molecular Formula: C10H14O4
Linear Structure Formula: C10H14O4
Molecular Weight: 198.219 InChI Key: WTPYFJNYAMXZJG-UHFFFAOYSA-N
1
Synthesize | Hide Details Find similar Chemical Names and Synonyms 1,4-bis(2-hydroxyethoxy)benzene, p-bis(2-hydroxyethoxy)benzene Identification Substance Label (12) Label
Reference
14
Twibanire, Jean-D'Amour K.; Paul, Nawal K.; Grindley, T. Bruce
New Journal of Chemistry, 2015 , vol. 39, # 5 p. 4115 - 4127 Title/Abstract Full Text View citing articles Show Details
1d
Zhang, Ben; Zavalij, Peter Y.; Isaacs, Lyle
Organic and Biomolecular Chemistry, 2014 , vol. 12, # 15 p. 2413 - 2422 Title/Abstract Full Text View citing articles Show Details
1
Keefe, Genny E.; Twibanire, Jean-D'Amour K.; Grindley, T. Bruce; Shaver, Michael P.
N° of preparations All Preps | All Reactions
Available Data
N° of ref.
11 prep out of 138 reactions.
Identification Physical Data (21) Spectra (14)
84
Canadian Journal of Chemistry, 2013 , vol. 91, # 6 p. 392 - 397 Title/Abstract Full Text View citing articles Show Details
2a
Ito, Hiroshi; Ishida, Yasuhiro; Saigo, Kazuhiko
Tetrahedron Letters, 2006 , vol. 47, # 18 p. 3095 - 3098 Title/Abstract Full Text View citing articles Show Details
educt to 9
Wong, Wallace W. H.; Curiel, David; Cowley, Andrew R.; Beer, Paul D.
Dalton Transactions, 2005 , # 2 p. 359 - 364 Title/Abstract Full Text View citing articles Show Details
4
Ikeda, Taichi; Asakawa, Masumi; Miyake, Koji; Shimizu, Toshimi
Chemistry Letters, 2004 , vol. 33, # 11 p. 1418 - 1419 Title/Abstract Full Text View citing articles Show Details
4a
Ono, Katsuhiko; Yamada, Satsuki; Ohkita, Masakazu; Saito, Katsuhiro; Tanaka, Shoji; Hanaichi, Takamasa
Chemistry Letters, 2003 , vol. 32, # 6 p. 516 - 517 Title/Abstract Full Text View citing articles Show Details
6
Rajakumar, Perumal; Srinivasan, Kannupal
European Journal of Organic Chemistry, 2003 , # 7 p. 1277 - 1284 Title/Abstract Full Text View citing articles Show Details
2e
Wariishi, Koji; Morishima, Sin-Ichi; Inagaki, Yoshio
Organic Process Research and Development, 2003 , vol. 7, # 1 p. 98 - 100 Title/Abstract Full Text View citing articles Show Details
8
Chambers; Kurrasch-Orbaugh; Parker; Nichols
Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details
8a
Gibson, Harry W.; Nagvekar, Devdatt S.; Delaviz, Yadollah; Bryant, William S.
Canadian Journal of Chemistry, 1998 , vol. 76, # 10 p. 1429 - 1436 Title/Abstract Full Text View citing articles Show Details
BHEB
Asakawa, Masumi; Brown, Christopher L.; Menzer, Stephan; Raymo, Francisco M.; Stoddart, J. Fraser; Williams, David J.
Journal of the American Chemical Society, 1997 , vol. 119, # 11 p. 2614 - 2627 Title/Abstract Full Text View citing articles Show Details
Patent-Specific Data (3) Related Markush Structure (RN)
Location in Patent
Reference
Page/Page column
Merck Patent GmbH; Rudolph, Thomas; Eisenberg, Sylvia
Patent: US2015/118165 A1, 2015 ; Title/Abstract Full Text Show Details
Dai, Shenghong A.; Lin, Hsing-Yo; Wen, Chien-Sheng
Patent: US2008/228010 A1, 2008 ;
18478811
Title/Abstract Full Text Show Details
Claim
Ethicon, Inc.
Patent: US4689424 A1, 1987 ; Title/Abstract Full Text Show Details
Bayer Aktiengesellschaft
Patent: US4739042 A1, 1988 ; Title/Abstract Full Text Show Details
Ciba Specialty Chemicals Corporation
Patent: US6475505 B1, 2002 ; Title/Abstract Full Text Show Details
AorTech Biomaterials Pty Ltd
Patent: EP1000070 B1, 2003 ; Title/Abstract Full Text Show Details
Derivative (1) Comment (Derivative)
Reference
1.4-bis-<2-triphenylmethoxy-ethoxy>-benzene (mp: 200 degree )
Shukis; Tallman
Journal of the American Chemical Society, 1944 , vol. 66, p. 1462
Full Text View citing articles Show Details
Physical Data Melting Point (11) Melting Point
Solvent (Melting Point)
Twibanire, Jean-D'Amour K.; Al-Mughaid, Hussein; Grindley, T. Bruce
Tetrahedron, 2010 , vol. 66, # 50 p. 9602 - 9609 Title/Abstract Full Text View citing articles Show Details
102 - 104 °C
102 - 106 °C
Reference
ethanol water
Lin, Hsing-Yo; Dai, Shenghong A.
Journal of the Chinese Chemical Society, 2010 , vol. 57, # 2 p. 167 - 173 Title/Abstract Full Text View citing articles Show Details
101.5 - 102.3 °C
Pirrung, Michael C.; Nunn, David S.
Tetrahedron, 1996 , vol. 52, # 16 p. 5707 - 5738 Title/Abstract Full Text View citing articles Show Details
103 - 105 °C
Goosen,A.; Mccleland,C.W.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1978 , p. 646 Full Text Show Details
119 - 121 °C
Kalvoda,L.
Collection of Czechoslovak Chemical Communications, 1973 , vol. 38, p. 1679 - 1692 Full Text View citing articles Show Details
108 °C
Sakakibara et al.
Kogyo Kagaku Zasshi, 1970 , vol. 73, p. 1196,1197, 1200 Chem.Abstr., 1970 , vol. 73, # 88523 Full Text Show Details
H2O
104 - 106 °C
Koppers Company, USA
Patent: DE1958725 , 1970 ; Chem.Abstr., vol. 73, # 55802 Full Text Show Details
104 °C
Hoechst AG
Patent: DE1920032 , 1970 ; Full Text Show Details
Mitsui Petrochemical Industries, Ltd.
Patent: JP6927570 , 1967 ; Chem.Abstr., 1970 , vol. 72, # 90052g Full Text Show Details
BASF
Patent: DE1096366 , 1958 ; Chem.Abstr., 1961 , # 21056 Full Text Show Details
104 - 105 °C
103 - 104 °C
toluene
Dyer; Scott
Journal of the American Chemical Society, 1957 , vol. 79, p. 672,674 Full Text Show Details
Shukis; Tallman
Journal of the American Chemical Society, 1944 , vol. 66, p. 1462 Full Text View citing articles Show Details
105 °C
Association (MCS) (7) Partner (Association (MCS))
Solvent (Association (MCS))
Temperature (Association (MCS))
Stability constant of the complex with ...
CBPQT(4+)
acetonitrile
24.9 °C
Castro, Rene; Davidov, Pablo D.; Kumar, Kaipeuchery A.; Marchand, Alan P.; Evanseck, Jeffrey D.; Kaifer, Angel E.
Journal of Physical Organic Chemistry, 1997 , vol. 10, # 5 p. 369 - 382 Title/Abstract Full Text Show Details
UV/VIS spectrum of the complex
CBPQT(4+)
acetonitrile
24.9 °C
Castro, Rene; Davidov, Pablo D.; Kumar, Kaipeuchery A.; Marchand, Alan P.; Evanseck, Jeffrey D.; Kaifer, Angel E.
Journal of Physical Organic Chemistry, 1997 , vol. 10, # 5 p. 369 - 382 Title/Abstract Full Text Show Details
Description (Association (MCS))
Reference
UV/VIS spectrum of the complex
cyclobis(paraquat-1,4-phenylene) tetrakis(hexafluorophosphate)
acetonitrile
24.9 °C
Castro, Rene; Nixon, Kendric R.; Evanseck, Jeffrey D.; Kaifer, Angel E.
Journal of Organic Chemistry, 1996 , vol. 61, # 21 p. 7298 - 7303 Title/Abstract Full Text View citing articles Show Details
Stability constant of the complex with ...
cyclobis(paraquat-1,4-phenylene) tetrakis(hexafluorophosphate)
acetonitrile
24.9 °C
Castro, Rene; Nixon, Kendric R.; Evanseck, Jeffrey D.; Kaifer, Angel E.
Journal of Organic Chemistry, 1996 , vol. 61, # 21 p. 7298 - 7303 Title/Abstract Full Text View citing articles Show Details
Further physical properties of the complex
CBPQT(4+)
Further physical properties of the complex
1,1'-dibenzyl-4,4'-bipyridinium
Further physical properties of the complex
C30H30N4(4+)
Smith, Eliot A.; Lilienthal, Ronald R.; Fonseca, Robert J.; Smith, Diane K. Analytical Chemistry, 1994 , vol. 66, # 19 p. 3013 - 3020 Title/Abstract Full Text View citing articles Show Details
Smith, Eliot A.; Lilienthal, Ronald R.; Fonseca, Robert J.; Smith, Diane K. Analytical Chemistry, 1994 , vol. 66, # 19 p. 3013 - 3020 Title/Abstract Full Text View citing articles Show Details
Smith, Eliot A.; Lilienthal, Ronald R.; Fonseca, Robert J.; Smith, Diane K. Analytical Chemistry, 1994 , vol. 66, # 19 p. 3013 - 3020 Title/Abstract Full Text View citing articles Show Details
Crystal Property Description (1) Colour & Other Properties
Reference
colourless
Twibanire, Jean-D'Amour K.; Al-Mughaid, Hussein; Grindley, T. Bruce
Tetrahedron, 2010 , vol. 66, # 50 p. 9602 - 9609 Title/Abstract Full Text View citing articles Show Details
Solubility (MCS) (1) Solubility
Saturation
11.695 g·l-1
in pure solvent
Temperature (Solubility (MCS))
Solvent (Solubility (MCS))
25 °C
H2O
Reference Molyneux, Philip; Vekavakayanondha, Sudhe
Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, 1986 , vol. 82, p. 291 - 318 Title/Abstract Full Text View citing articles Show Details
Transport Phenomena (MCS) (1) Description (Transport Phenomena (MCS))
Partner (Transport Phenomena (MCS))
Solvent (Transport Phenomena (MCS))
Temperature (Transport Phenomena (MCS))
Viscosity
poly(vinylpirrolidone)
H2O
20 °C
Reference Molyneux, Philip; Vekavakayanondha, Sudhe
Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, 1986 , vol. 82, p. 635 - 662 Title/Abstract Full Text View citing articles Show Details
Spectra NMR Spectroscopy (8) Description (NMR Spectroscopy)
Nucleus (NMR Spectroscopy)
Solvents (NMR Spectroscopy)
Chemical shifts Spectrum
1H
dimethylsulfoxided6
Chemical shifts Spectrum
13C
dimethylsulfoxided6
Chemical shifts Spectrum
1H
dimethylsulfoxided6
Temperature (NMR Spectroscopy)
Frequency (NMR Spectroscopy) 400 MHz
500.1 MHz
Original Text (NMR Spectroscopy)
Location
Comment (NMR Spectroscopy)
Reference
supporting information
Yang, Wanggui; Xia, Ping Fang; Wong, Man Shing
Organic Letters, 2010 , vol. 12, # 18 p. 4018 4021 Title/Abstract Full Text View citing articles Show Details
supporting information
Yang, Wanggui; Xia, Ping Fang; Wong, Man Shing
Organic Letters, 2010 , vol. 12, # 18 p. 4018 4021 Title/Abstract Full Text View citing articles Show Details
supporting information
Twibanire, Jean-D'Amour K.; Al-Mughaid, Hussein; Grindley, T. Bruce
Tetrahedron, 2010 , vol. 66, # 50 p. 9602 -
9609 Title/Abstract Full Text View citing articles Show Details
Chemical shifts Spectrum
13C
dimethylsulfoxided6
125.7 MHz
Chemical shifts
1H
chloroform-d1
200 MHz
Lin, Hsing-Yo; Dai, Shenghong A.
Journal of the Chinese Chemical Society, 2010 , vol. 57, # 2 p. 167 - 173 Title/Abstract Full Text View citing articles Show Details
1H NMR (R=H. a=1. b=1), d=2.04 (s. 2H. OH), 3.79 (t. 4H), 3.95 (t. 4H), 6.84 (s. 4H. aromatics).
1H
Chemical shifts
1H
CDCl3
Chemical shifts
1H
CD3CN
Twibanire, Jean-D'Amour K.; Al-Mughaid, Hussein; Grindley, T. Bruce
Tetrahedron, 2010 , vol. 66, # 50 p. 9602 9609 Title/Abstract Full Text View citing articles Show Details
supporting information
Signals given
Dai, Shenghong A.; Lin, Hsing-Yo; Wen, Chien-Sheng
Patent: US2008/228010 A1, 2008 ; Title/Abstract Full Text Show Details
Pirrung, Michael C.; Nunn, David S.
Tetrahedron, 1996 , vol. 52, # 16 p. 5707 5738 Title/Abstract Full Text View citing articles Show Details
Anelli, Pier Lucio; Ashton, Peter R.; Ballardini, Roberto; Balzani, Vincenzo; Delgado, Milagros; Gandoffi, Maria Teresa; Goodnow, Timothy T.; Kaifer, Angel E.; Philp, Douglas; Pietraszkiewicz, Marek; Prodi, Luca; Reddington, Mark V.; Slawin, Alexandra M.Z.; Spencer, Neil; Fraser Stoddart; Vicent, Cristina; Williams, David J.
Journal of the American Chemical Society, 1992 , vol. 114, # 1 p. 193 - 218 Title/Abstract Full Text View citing articles Show Details
20 °C
IR Spectroscopy (2) Description (IR Spectroscopy)
Solvent (IR Spectroscopy)
Comment (IR Spectroscopy)
Reference
Bands
KBr
3270 - 1050 cm**(-1)
Pirrung, Michael C.; Nunn, David S.
Tetrahedron, 1996 , vol. 52, # 16 p. 5707 - 5738 Title/Abstract Full Text View citing articles Show Details
Sakakibara et al.
Kogyo Kagaku Zasshi, 1970 , vol. 73, p. 1196,1197, 1200 Chem.Abstr., 1970 , vol. 73, # 88523 Full Text Show Details
IR
Mass Spectrometry (2) Description (Mass Spectrometry)
Location
Reference
FAB (Fast atom bombardment) Spectrum
supporting information
Yang, Wanggui; Xia, Ping Fang; Wong, Man Shing
Organic Letters, 2010 , vol. 12, # 18 p. 4018 - 4021 Title/Abstract Full Text View citing articles Show Details
HRMS (High resolution mass spectrometry) MALDI-TOF (Matrix assisted laser desorption ionization - time of flight) Spectrum
supporting information
Yang, Wanggui; Xia, Ping Fang; Wong, Man Shing
Organic Letters, 2010 , vol. 12, # 18 p. 4018 - 4021 Title/Abstract Full Text View citing articles Show Details
UV/VIS Spectroscopy (2) Description (UV/VIS Spectroscopy)
Solvent (UV/VIS Spectroscopy)
Absorption Maxima (UV/VIS)
Ext./Abs. Coefficient
Absorption maxima
methanol
232 nm 288 nm
3162 l·mol-1cm-1 2951 l·mol-1cm-1
Reference Pirrung, Michael C.; Nunn, David S.
Tetrahedron, 1996 , vol. 52, # 16 p. 5707 - 5738 Title/Abstract Full Text View citing articles Show Details
Absorption maxima
H2O
285 nm
2300 l·mol-1cm-1
Molyneux, Philip; Vekavakayanondha, Sudhe
Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, 1986 , vol. 82, p. 291 - 318 Title/Abstract Full Text View citing articles Show Details