124276-34-2

Basic information

• Product Name: 1-(3-CHLOROPHENYL)CYCLOPROPANECARBOXYLIC ACID
• Synonyms: 1-(3-CHLOROPHENYL)CYCLOPROPANECARBOXYLIC ACID;1-(3-CHLOROPHENYL)CYCLOPROPANE-1-CARBOXYLIC ACID;AKOS BBV-004387
• CAS NO: 124276-34-2
• Molecular Formula: C₁₀H₉ClO₂
• Molecular Weight: 196.63
• Product Categories: pharmacetical;Carboxylic Acids;Carboxylic Acids;Ring Systems
• Mol File: 124276-34-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 350.261°C at 760 mmHg
• Flash Point: 165.632°C
• Appearance: /
• Density: 1.404g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: Room temperature.
• PKA: 4.11±0.20(Predicted)
• CAS DataBase Reference: 1-(3-CHLOROPHENYL)CYCLOPROPANECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-CHLOROPHENYL)CYCLOPROPANECARBOXYLIC ACID(124276-34-2)
• EPA Substance Registry System: 1-(3-CHLOROPHENYL)CYCLOPROPANECARBOXYLIC ACID(124276-34-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36-41
• Safety Statements: 26-39
• Hazardous Substances Data: 124276-34-2(Hazardous Substances Data)

Usage

General Description

1-(3-Chlorophenyl)cyclopropanecarboxylic acid is a chemical compound with a molecular formula C10H9ClO2. It is a cyclopropane derivative with a carboxylic acid functional group and a chlorophenyl substitution. 1-(3-Chlorophenyl)cyclopropanecarboxylic acid is used in organic synthesis and pharmaceutical research as a building block for the synthesis of various biologically active molecules. It has potential applications in the development of new drugs and agrochemicals. Additionally, it may also be used as a reagent in chemical reactions and as a precursor for the production of other organic compounds.

InChI:InChI=1/C10H9ClO2/c11-8-3-1-2-7(6-8)10(4-5-10)9(12)13/h1-3,6H,4-5H2,(H,12,13)

Upstream product

• 1529-41-5 3-chloro-benzeneacetonitrile 
• 124276-32-0 1-(3-chloro-phenyl)cyclopropanecarbonitrile 

Downstream Products

• 943118-81-8 methyl 1-(3-chlorophenyl)cyclopropanecarboxylate 
• 98480-33-2 (1-(3-chlorophenyl)cyclopropyl)methanol 
• 1252641-14-7 (4R)-1-{[1-(3-chlorophenyl)cyclopropyl]carbonyl}-4-[(2-chlorophenyl)sulfonyl]-N-(1-cyanocyclopropyl)-L-prolinamide 
• 1252638-93-9 (4R)-1-{[1-(3-chlorophenyl)cyclopropyl]carbonyl}-4-{[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]sulfonyl}-N-(1-cyanocyclopropyl)-L-prolinamide 
• 501698-47-1 1-(3-chlorophenyl)cyclopropanecarbonyl chloride 

Relevant articles and documents

Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes

We herein report an Ir-catalyzed enantioselective C(sp3)-H borylation of cyclopropanecarboxamides using a chiral bidentate boryl ligand for the first time. A variety of substrates with α-quaternary carbon centers could be compatible in this reaction to provide β-borylated products with good to excellent enantioselectivities. We have also demonstrated that the borylated products can be used as versatile precursors engaging in stereospecific transformations of C-B bonds, including the synthesis of a bioactive compound Levomilnacipran.

Discovery of 2-[1-(4-Chlorophenyl)cyclopropyl]-3-hydroxy-8- (trifluoromethyl)quinoline-4-carboxylic acid (PSI-421), a P-selectin inhibitor with improved pharmacokinetic properties and oral efficacy in models of vascular injury

Previously, we reported the discovery of PSI-697 (1a), a C-2 benzyl substituted quinoline salicylic acid-based P-selectin inhibitor. It is active in a variety of animal models of cardiovascular disease. Compound 1a has also been shown to be well tolerated and safe in healthy volunteers at doses of up to 1200 mg in a phase 1 single ascending dose study. However, its oral bioavailability was low. Our goal was to identify a back up compound with equal potency, increased solubility, and increased exposure. We expanded our structure-activity studies in this series by branching at the α position of the C-2 benzyl side chain and through modification of substituents on the carboxylic A-ring of the quinoline. This resulted in discovery of PSI-421 with marked improvement in aqueous solubility and pharmacokinetic properties. This compound has shown oral efficacy in animal models of arterial and venous injury and was selected as a preclinical development compound for potential treatment of such diseases as atherosclerosis and deep vein thrombosis.

Heteroaryl-Pyrazole Derivatives as Cannabinoid CB1 Receptor Antagonists

A heteroaryl-pyrazole compound of formula (I) or a pharmaceutically acceptable salt thereof is effective as a cannabinoid CB1 receptor inverse agonist or antagonist, which is useful for preventing or treating obesity and obesity-related metabolic disorders. The present invention also provides a method for preparing the inventive heteroaryl-pyrasole compounds or a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing same, and a method for preventing or treating obesity and obesity-related metabolic disorders.