113111-32-3

Basic information

• Product Name: 1,2-Cyclopropanedicarboxylic acid, 1-(4-methylphenyl)-
• Synonyms: 1,2-Cyclopropanedicarboxylic acid, 1-(4-methylphenyl)-;cis-1-(p-tolyl)-1,2-cyclopropanedicarboxylic acid;1-(p-Tolyl)cyclopropane-1,2-dicarboxylic acid
• CAS NO: 113111-32-3
• Molecular Formula: C₁₂H₁₂O₄
• Molecular Weight: 220.22
• Mol File: 113111-32-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 409.342°C at 760 mmHg
• Flash Point: 215.518°C
• Appearance: /
• Density: 1.406g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.623
• CAS DataBase Reference: 1,2-Cyclopropanedicarboxylic acid, 1-(4-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Cyclopropanedicarboxylic acid, 1-(4-methylphenyl)-(113111-32-3)
• EPA Substance Registry System: 1,2-Cyclopropanedicarboxylic acid, 1-(4-methylphenyl)-(113111-32-3)

Safety Data

• Hazardous Substances Data: 113111-32-3(Hazardous Substances Data)

Usage

General Description

1,2-Cyclopropanedicarboxylic acid, 1-(4-methylphenyl)- is a chemical compound that contains a cyclopropane ring and a carboxylic acid functional group. It is also known by the molecular formula C11H10O4. 1,2-Cyclopropanedicarboxylic acid, 1-(4-methylphenyl)- is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals. Its unique structural properties, including the presence of a cyclopropane ring and a substituted phenyl group, make it a valuable intermediate in organic chemistry. Additionally, it has been studied for its potential pharmacological properties, including its potential use as an anticonvulsant and as an anti-inflammatory agent.

InChI:InChI=1/C12H12O4/c1-7-2-4-8(5-3-7)12(11(15)16)6-9(12)10(13)14/h2-5,9H,6H2,1H3,(H,13,14)(H,15,16)

Upstream product

• 60162-33-6 chloro-p-tolyl-acetic acid methyl ester 
• 292638-85-8 acrylic acid methyl ester 
• 77053-52-2 methyl bromo(4-methylphenyl)acetate 
• 66504-76-5 (1R,2S)-1-p-Tolyl-cyclopropane-1,2-dicarboxylic acid dimethyl ester 

Downstream Products

• 66504-75-4 1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexane hydrochloride 
• 66504-87-8 (+/-)-1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexan-2,4-dione 
• 66504-84-5 (1R,5S)-1-p-Tolyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione 
• 66504-77-6 (1S,5R)-1-p-Tolyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione 
• 113111-37-8 1-(4-Dibromomethyl-phenyl)-3-methyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione 
• 113111-36-7 1-<4-(bromomethyl)phenyl>-3-azabicyclo<3.1.0>hexane-2,4-dione 
• 113111-38-9 1-<4-(hydroxymethyl)phenyl>-3-azabicyclo<3.1.0>hexane-2,4-dione 
• 113111-39-0 1-(4-formylphenyl)-3-azabicyclo<3.1.0>hexane-2,4-dione 
• 113111-35-6 3-Methyl-1-p-tolyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione 
• 66504-83-4 (1R,2S)-(+)-1-(4-methylphenyl)-1,2-cyclopropanedicarboxylic acid 
• 66504-85-6 (1S,2R)-(-)-1-(4-methylphenyl)-1,2-cyclopropanedicarboxylic acid 

Relevant articles and documents

Polymorphs of bicifadine hydrochloride

A new polymorphic crystalline form of bicifadine hydrochloride, designated form B, which is more thermodynamically stable than the previously known polymorphic form of bicifadine hydrochloride, designated as form A, methods for preparing said crystalline

1-Aryl-3-azabicyclohexanes, a New Series of Nonnarcotic Analgesic Agents

A series of 1-aryl-3-azabicyclohexanes was synthesized by hydride reduction of 1-arylcyclopropanedicarboximides.Hydroxyphenyl analogues 20, 22, and 24 were prepared by EtSNa-DMF ether cleavage of the corresponding methoxyphenyl analogues 2m, 2n, and 23, respectively, with the secondary amines 20 and 22 going through the N-formyl intermediates 19 and 21.The p-ethoxy analogue 26 was obtained by O-ethylation of 19, followed by base hydrolysis of the amide 25.The greatest analgesic potency in mouse writhing and rat paw-pain assays was observed for para-substituted compounds.Bicifadine, 1-(4-methylphenyl)-3-azabicyclohexane (2b), was the most potent member of the series and is presently undergoing clinical trials in man.Analgesic activity of 2b is limited to the (+) enantiomer 2v, which has the 1R,5S absolute configuration as determined by single-crystal X-ray analysis.The N-methyl analogue (27d) of 2b showed significant analgesic potency, whereas the N-allyl (27a), N-(cyclopropylmethyl) (27b), and N-(n-hexyl) (27c) analogues were inactive.Bicifadine (2b) showed a nonnarcotic profile different from analogous azabicycloalkane and 3-phenylpyrrolidine analgesics.

Azabicyclohexanes

Substituted 3-azabicyclo[3.1.0]hexanes, acid addition salts, method of use and method of preparation are described. The compounds have anxiolytic and analgesic activity.