1,1'-(1,3-Phenylene)bis(1H-pyrrole-2,5-dione)

Page 1

Reaxys

PubChem

eMolecules

Reactions (13)

Substances (1)

Structure

Citations (37)

N° of preparations All Preps | All Reactions

Structure/Compound Data Chemical Name: N,N'-(1,3-phenylene)dimaleimide Reaxys Registry Number: 249503

CAS Registry Number: 3006-93-7 Type of Substance: heterocyclic Molecular Formula: C14H8N2O4

Linear Structure Formula: C14H8N2O4

Molecular Weight: 268.229 InChI Key: IPJGAEWUPXWFPL-UHFFFAOYSA-N

1

3 prep out of 13 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms N,N'-(1,3-phenylene)dimaleimide, N,N-(1,3-phenylene)dimaleimide, N,N'-m-phenylenedimaleimide, 1,1'-m-phenylene-bis-pyrrole-2,5-dione, 1,1'-mPhenylen-bis-pyrrol-2,5-dion, 1,1'-(1,3-phenylene)bis-1H-pyrrole-2,5-dione, N,N'-meta-phenylene-bis-maleimide Identification Substance Label (1) Label

Reference

IV

Vereshchagina; Timosheva; Chachkov

Russian Journal of Organic Chemistry, 2013 , vol. 49, # 10 p. 1482 - 1485 Zh. Org. Khim., 2013 , vol. 49, # 10 p. 1503 - 1506,4 Title/Abstract Full Text View citing articles Show Details

Patent-Specific Data (3) Prophetic Compound

Related Markush Structure (RN)

Location in Patent

Reference

Available Data

N° of ref.

Identification Physical Data (21) Spectra (5) Bioactivity (6) Other Data (3)

37


prophetic product

27956613

Paragraph 0017

PUGH, Coleen; THE UNIVERSITY OF AKRON; WATT, Paula; MEHTA, Brinda

Patent: WO2015/35156 A1, 2015 ; Title/Abstract Full Text Show Details

Claim

DAI Nippon Printing Co., Ltd.; Isao Karube

Patent: US6627397 B1, 2003 ; Title/Abstract Full Text Show Details

Ciba-Geigy Corporation

Patent: US4371719 A1, 1983 ;

prophetic product

Title/Abstract Full Text Show Details

Rhone-Poulenc Specialites Chimiques

Patent: US4788295 A1, 1988 ; Title/Abstract Full Text Show Details

Physical Data Melting Point (13) Melting Point

Solvent (Melting Point)

Reference

201.85 °C

Biran, V. V.; Zlotnikov, I. I.; Kudina, E. F.; Lisovskii, V. V.

J. Appl. Chem. USSR (Engl. Transl.), 1990 , vol. 63, # 11.2 p. 2515 - 2519,2328 - 2331 Title/Abstract Full Text Show Details

198 - 200 °C

Khabenko, A. V.; Kalinchikov, V. E.; Marinyuk, L. I.; Rakhmanova, T. V.; Dolmatov, S. A.

J. Appl. Chem. USSR (Engl. Transl.), 1984 , vol. 57, # 8 p. 1827 - 1830,1691 - 1694 Title/Abstract Full Text Show Details

208 °C

E.I. du Pont Patent: FR2350349DE2719903 , 19771977 ; Chem.Abstr., vol. 88, # 62007 Full Text Show Details

203 °C

Put; Schryver

Journal of the American Chemical Society, 1973 , vol. 95, p. 137,139,140 Full Text View citing articles Show Details

203 - 204 °C

Chernysheva et al.

Patent: SU240701 , 1972 ; Ref. Zh., Khim., 1973 , vol. 9, # N134P Full Text Show Details

198.5 °C

Dzamukashvili et al.

Doklady Physical Chemistry, 1972 , vol. 203, p. 242 Full Text Show Details

204 °C

Rhone-Poulenc

Patent: DE2040094 , 1971 ; Chem.Abstr., vol. 74, # 111591 Full Text Show Details

201 - 202 °C

Lific et al.

Metody Polucheniya Khimicheskikh Reaktivov i Preparatov, 1970 , vol. 22, p. 118,119-122 Chem.Abstr., vol. 77, # 34229m Chem. Zentralbl., Ref.Zh.Khim. <1971> Nr.11 Zh204 Full Text Show Details

198 - 199 °C

Iwakura,Y. et al.

Bulletin of the Chemical Society of Japan, 1968 , vol. 41, # 7 p. 1648 - 1653 Full Text View citing articles Show Details

Du Pont de Nemours and Co.

Patent: US2444536 , 1946 ; Full Text Show Details

202.4 - 205.2 °C

du Pont

Patent: US3127414 , 1962 ; Chem.Abstr., vol. 60, # 14444 Full Text Show Details

202 °C

Kovacic; Hein


Rubber Chemistry and Technology, 1962 , vol. 35, p. 520 Full Text Show Details

202 °C

toluene ethanol

Kovacic; Hein

Journal of the American Chemical Society, 1959 , vol. 81, p. 1187,1189 Full Text Show Details

202 °C

aq. dioxane

Kovacic; Hein

Journal of the American Chemical Society, 1959 , vol. 81, p. 1187,1189 Full Text Show Details

Association (MCS) (3) Description (Association (MCS))

Partner (Association (MCS))

Solvent (Association (MCS))

Temperature (Association (MCS))

Reference Adigezalov, N. R.; Kiselev, V. D.; Konovalov, A. I.

Journal of Organic Chemistry USSR (English Translation), 1991 , vol. 27, # 8 p. 1558 - 1562 Zhurnal Organicheskoi Khimii, 1991 , vol. 27, # 8 p. 1774 - 1779 Title/Abstract Full Text Show Details

UV/VIS spectrum of the complex

Hexamethylbenzene

UV/VIS spectrum of the complex

Hexamethylbenzene

dioxane

Enthalpy of association

Gallium trichloride

benzene

Adigezalov, N. R.; Kiselev, V. D.; Konovalov, A. I.

Journal of Organic Chemistry USSR (English Translation), 1989 , vol. 25, # 3.1 p. 486 - 490 Zhurnal Organicheskoi Khimii, 1989 , vol. 25, # 3 p. 542 - 547 Title/Abstract Full Text Show Details

25 °C

Kiselev, V. D.; Adigezalov, N. R.; Akhmedov, I. M.; Konovalov, A. I.

Journal of Organic Chemistry USSR (English Translation), 1989 , vol. 25, # 3.1 p. 491 - 495 Zhurnal Organicheskoi Khimii, 1989 , vol. 25, # 3 p. 548 - 552 Title/Abstract Full Text Show Details

Crystal Property Description (1) Colour & Other Properties

Reference

gelb

Du Pont de Nemours and Co.

Patent: US2444536 , 1946 ; Full Text Show Details

Kovacic; Hein

Journal of the American Chemical Society, 1959 , vol. 81, p. 1187,1189 Full Text Show Details

Electrical Moment (1) Description (Electrical Moment)

Moment (Electrical Moment)

Method (Electrical Moment)

Dipole moment

2.21 D

Other methods

Reference Vereshchagina; Timosheva; Chachkov

Russian Journal of Organic Chemistry, 2013 , vol. 49, # 10 p. 1482 1485 Zh. Org. Khim., 2013 , vol. 49, # 10 p. 1503 - 1506,4 Title/Abstract Full Text View citing articles Show Details

Electron Binding (1) Description (Electron Binding)

Reference

Electron affinity

Adigezalov, N. R.; Kiselev, V. D.; Konovalov, A. I.

Journal of Organic Chemistry USSR (English Translation), 1989 , vol. 25, # 3.1 p. 486 - 490 Zhurnal Organicheskoi Khimii, 1989 , vol. 25, # 3 p. 542 - 547 Title/Abstract Full Text Show Details

Further Information (1) Description (Further Information)

Reference

Further information

Feast et al.

Organic Mass Spectrometry, 1970 , vol. 3, p. 507,510 Full Text Show Details


Transport Phenomena (MCS) (1) Description (Transport Phenomena (MCS))

Partner (Transport Phenomena (MCS))

Temperature (Transport Phenomena (MCS))

Viscosity

epoxy acrylate oligomer

35 - 50 °C

Reference Kalinina; Vasil'eva; Migunova; Ivanov

Russian Journal of Applied Chemistry, 1997 , vol. 70, # 4 p. 643 - 646 Title/Abstract Full Text View citing articles Show Details

Spectra NMR Spectroscopy (1) Description (NMR Spectroscopy)

Reference

NMR

Put; Schryver

Journal of the American Chemical Society, 1973 , vol. 95, p. 137,139,140 Full Text View citing articles Show Details

IR Spectroscopy (3) Description (IR Spectroscopy)

Solvent (IR Spectroscopy)

Comment (IR Spectroscopy)

Spectrum

KBr

3500 - 500 cm**(-1)

Reference Biran, V. V.; Zlotnikov, I. I.; Kudina, E. F.; Lisovskii, V. V.

J. Appl. Chem. USSR (Engl. Transl.), 1990 , vol. 63, # 11.2 p. 2515 2519,2328 - 2331 Title/Abstract Full Text Show Details

IR

Put; Schryver

Journal of the American Chemical Society, 1973 , vol. 95, p. 137,139,140 Full Text View citing articles Show Details

Spectrum

Dzamukashvili et al.

Doklady Physical Chemistry, 1972 , vol. 203, p. 242 Full Text Show Details

Mass Spectrometry (1) Reference Feast et al.

Organic Mass Spectrometry, 1970 , vol. 3, p. 507,510 Full Text Show Details

Bioactivity Pharmacological Data (6) 1 of 6

Comment (Pharmacological Data)

Bioactivities present

Reference

E. I. Du Pont de Nemours and Company Patent: US4154737 A1, 1979 ; Title/Abstract Full Text Show Details

Ciba-Geigy Corporation

Patent: US4371719 A1, 1983 ; Title/Abstract Full Text Show Details

Rhone-Poulenc Specialites Chimiques

Patent: US4788295 A1, 1988 ; Title/Abstract Full Text Show Details

Iwakura,Y. et al.

Bulletin of the Chemical Society of Japan, 1968 , vol. 41, # 7 p. 1648 - 1653 Full Text View citing articles Show Details

DAI Nippon Printing Co., Ltd.; Isao Karube

Patent: US6627397 B1, 2003 ; Title/Abstract Full Text Show Details

KANE BIOTECH INC.


Patent: WO2005/94579 A1, 2005 ; Title/Abstract Full Text Show Details

Du Pont de Nemours and Co.

Patent: US2444536 , 1946 ; Full Text Show Details

Kovacic; Hein

Journal of the American Chemical Society, 1959 , vol. 81, p. 1187,1189 Full Text Show Details

Put; Schryver

Journal of the American Chemical Society, 1973 , vol. 95, p. 137,139,140 Full Text View citing articles Show Details

Feast et al.

Organic Mass Spectrometry, 1970 , vol. 3, p. 507,510 Full Text Show Details

Lific et al.

Metody Polucheniya Khimicheskikh Reaktivov i Preparatov, 1970 , vol. 22, p. 118,119-122 Chem.Abstr., vol. 77, # 34229m Chem. Zentralbl., Ref.Zh.Khim. <1971> Nr.11 Zh204 Full Text Show Details

Dzamukashvili et al.

Doklady Physical Chemistry, 1972 , vol. 203, p. 242 Full Text Show Details

Kovacic; Hein

Rubber Chemistry and Technology, 1962 , vol. 35, p. 520 Full Text Show Details

Harris; Norris

Journal of Heterocyclic Chemistry, 1972 , vol. 9, p. 1251 Full Text Show Details

E.I. du Pont Patent: FR2350349DE2719903 , 19771977 ; Chem.Abstr., vol. 88, # 62007 Full Text Show Details Rhone-Poulenc Patent: DE2040094 , 1971 ; Chem.Abstr., vol. 74, # 111591 Full Text Show Details Iwakura et al. Bulletin of the Chemical Society of Japan, 1965 , vol. 38, p. 335 Full Text Show Details du Pont Patent: US3127414 , 1962 ; Chem.Abstr., vol. 60, # 14444 Full Text Show Details Chernysheva et al. Patent: SU240701 , 1972 ; Ref. Zh., Khim., 1973 , vol. 9, # N134P Full Text Show Details De Schryver et al. Angewandte Chemie, 1969 , vol. 81, p. 224 Full Text Show Details 2 of 6

Comment (Pharmacological Data)

Bioactivities present

Reference

Adigezalov, N. R.; Kiselev, V. D.; Konovalov, A. I.

Journal of Organic Chemistry USSR (English Translation), 1989 , vol. 25, # 3.1 p. 486 - 490 Zhurnal Organicheskoi Khimii, 1989 , vol. 25, # 3 p. 542 - 547 Title/Abstract Full Text Show Details

Kiselev, V. D.; Adigezalov, N. R.; Akhmedov, I. M.; Konovalov, A. I.

Journal of Organic Chemistry USSR (English Translation), 1989 , vol. 25, # 3.1 p. 491 - 495 Zhurnal Organicheskoi Khimii, 1989 , vol. 25, # 3 p. 548 - 552 Title/Abstract Full Text Show Details

Adigezalov, N. R.; Kiselev, V. D.; Konovalov, A. I.

Journal of Organic Chemistry USSR (English Translation), 1989 , vol. 25, # 6.1 p. 1033 - 1039 Zhurnal Organicheskoi Khimii, 1989 , vol. 25, # 6 p. 1147 - 1153 Title/Abstract Full Text Show Details

Biran, V. V.; Zlotnikov, I. I.; Kudina, E. F.; Lisovskii, V. V.

J. Appl. Chem. USSR (Engl. Transl.), 1990 , vol. 63, # 11.2 p. 2515 - 2519,2328 - 2331 Title/Abstract Full Text Show Details Cella, James A. Journal of Organic Chemistry, 1988 , vol. 53, # 9 p. 2099 - 2103 Title/Abstract Full Text View citing articles Show Details Adigezalov, N. R.; Kiselev, V. D.; Konovalov, A. I. Journal of Organic Chemistry USSR (English Translation), 1991 , vol. 27, # 8 p. 1558 - 1562 Zhurnal Organicheskoi Khimii, 1991 , vol. 27, # 8 p. 1774 - 1779 Title/Abstract Full Text Show Details Pastor, Stephen D.; Hessell, Edward T. Journal of Organic Chemistry, 1988 , vol. 53, # 24 p. 5776 - 5779 Title/Abstract Full Text View citing articles Show Details Tarasova, O. A.; Amosova, S. V.; Trofimov, B. A. J. Appl. Chem. USSR (Engl. Transl.), 1983 , vol. 56, # 12 p. 2761 - 2763,2575 - 2576 Title/Abstract Full Text Show Details Khabenko, A. V.; Kalinchikov, V. E.; Marinyuk, L. I.; Rakhmanova, T. V.; Dolmatov, S. A.


J. Appl. Chem. USSR (Engl. Transl.), 1984 , vol. 57, # 8 p. 1827 - 1830,1691 - 1694 Title/Abstract Full Text Show Details Kalinina; Vasil'eva; Migunova; Ivanov Russian Journal of Applied Chemistry, 1997 , vol. 70, # 4 p. 643 - 646 Title/Abstract Full Text View citing articles Show Details Itahara Synthesis, 1997 , # 11 p. 1252 - 1254 Title/Abstract Full Text View citing articles Show Details Cheng; Gan; Shi; Wei Journal of Organic Chemistry, 2001 , vol. 66, # 19 p. 6369 - 6374 Title/Abstract Full Text View citing articles Show Details Rhein Chemie Rheinau GmbH Patent: US5994561 A1, 1999 ; Title/Abstract Full Text Show Details

Matuszak, Nicolas; Muccioli, Giulio G.; Labar, Geoffray; Lambert, Didier M.

Journal of Medicinal Chemistry, 2009 , vol. 52, # 23 p. 7410 - 7420 Title/Abstract Full Text View citing articles Show Details

Gole, Bappaditya; Bar, Arun Kumar; Mallick, Arijit; Banerjee, Rahul; Mukherjee, Partha Sarathi

Chemical Communications, 2013 , vol. 49, # 67 p. 7439 - 7441 Title/Abstract Full Text View citing articles Show Details

Vereshchagina; Timosheva; Chachkov

Russian Journal of Organic Chemistry, 2013 , vol. 49, # 10 p. 1482 - 1485 Zh. Org. Khim., 2013 , vol. 49, # 10 p. 1503 - 1506,4 Title/Abstract Full Text View citing articles Show Details

PUGH, Coleen; THE UNIVERSITY OF AKRON; WATT, Paula; MEHTA, Brinda

Patent: WO2015/35156 A1, 2015 ; Title/Abstract Full Text Show Details

3 of 6

4 of 6

5 of 6

Effect (Pharmacological Data)

monoglyceride lipase activity; inhibition of

Species or TestSystem (Pharmacological Data)

monoglyceride lipase of human

Further Details (Pharmacological Data)

inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

2.03 μmol/l

Reference

Matuszak, Nicolas; Muccioli, Giulio G.; Labar, Geoffray; Lambert, Didier M.

Journal of Medicinal Chemistry, 2009 , vol. 52, # 23 p. 7410 - 7420 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

monoglyceride lipase activity; inhibition of

Species or TestSystem (Pharmacological Data)

monoglyceride lipase of human

Results

molecular target: monoglyceride lipase

Reference

Matuszak, Nicolas; Muccioli, Giulio G.; Labar, Geoffray; Lambert, Didier M.

Journal of Medicinal Chemistry, 2009 , vol. 52, # 23 p. 7410 - 7420 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

fatty acid amide hydrolase activity; inhibition of

Species or TestSystem (Pharmacological Data)

fatty acid amide hydrolase of human

Results

molecular target: fatty acid amide hydrolase

Reference

Matuszak, Nicolas; Muccioli, Giulio G.; Labar, Geoffray; Lambert, Didier M.

Journal of Medicinal Chemistry, 2009 , vol. 52, # 23 p. 7410 - 7420 Title/Abstract Full Text View citing articles Show Details


6 of 6

Effect (Pharmacological Data)

fatty acid amide hydrolase activity; inhibition of

Species or TestSystem (Pharmacological Data)

fatty acid amide hydrolase of human

Further Details (Pharmacological Data)

inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

37.2 μmol/l

Reference

Matuszak, Nicolas; Muccioli, Giulio G.; Labar, Geoffray; Lambert, Didier M.

Journal of Medicinal Chemistry, 2009 , vol. 52, # 23 p. 7410 - 7420 Title/Abstract Full Text View citing articles Show Details

Other Data Use (2) Use Pattern

Reference

antibacterial, in mixture with a cationic polypeptide, an iron-sequestering glycoprotein or a quaternary ammonium compound

KANE BIOTECH INC.

Patent: WO2005/94579 A1, 2005 ; Title/Abstract Full Text Show Details

KANE BIOTECH INC.

Patent: WO2005/94579 A1, 2005 ;

thiol-specific reagent for inhibiting bacterial biofilms on devices

Title/Abstract Full Text Show Details

Quantum Chemical Calculations (1) Calculated Properties

Method (Quantum Chemical Calculations)

Reference

Dipole moment, dipole moment derivative Atom distances, angles

Ab initio calcns. (LCAO, GO SCF, DIM, SAMO, X-à, HartreeFock)

Vereshchagina; Timosheva; Chachkov

Russian Journal of Organic Chemistry, 2013 , vol. 49, # 10 p. 1482 1485 Zh. Org. Khim., 2013 , vol. 49, # 10 p. 1503 - 1506,4 Title/Abstract Full Text View citing articles Show Details


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