515179-19-8

Basic information

• Product Name: (1R,2S)-2-(4-fluorophenyl)cyclopropane-1-carboxylic acid
• CAS NO: 515179-19-8
• Molecular Weight: 180.179
• Mol File: 515179-19-8.mol
• Article Data: 26

Chemical Properties

• CAS DataBase Reference: (1R,2S)-2-(4-fluorophenyl)cyclopropane-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-2-(4-fluorophenyl)cyclopropane-1-carboxylic acid(515179-19-8)
• EPA Substance Registry System: (1R,2S)-2-(4-fluorophenyl)cyclopropane-1-carboxylic acid(515179-19-8)

Safety Data

• Hazardous Substances Data: 515179-19-8(Hazardous Substances Data)

Usage

Description

(1R,2S)-2-(4-fluorophenyl)cyclopropane-1-carboxylic acid is a chiral chemical compound characterized by a cyclopropane ring structure and a carboxylic acid functional group. The presence of the 4-fluorophenyl group endows it with potential for interaction with biological targets, making it a promising candidate for pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
(1R,2S)-2-(4-fluorophenyl)cyclopropane-1-carboxylic acid is used as a building block for the synthesis of pharmaceuticals due to its unique structural and stereochemical properties. Its ability to interact with biological targets makes it a valuable component in the development of new drugs.
Used in Analytical Chemistry:
(1R,2S)-2-(4-fluorophenyl)cyclopropane-1-carboxylic acid is used as a reference standard in analytical chemistry. Its distinct stereochemistry allows for precise measurements and comparisons in various chemical analyses, ensuring accurate results in research and quality control processes.

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 405-99-2 para-fluorostyrene 
• 893751-08-1 trans-methyl 2-(4-fluorophenyl)cyclopropanecarboxylate 
• 214360-58-4 2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1759-53-1 cyclopropanecarboxylic acid 
• 352-34-1 4-fluoro-1-iodobenzene 
• 243665-10-3 (E)-3-(4-fluorophenyl)-N-methoxy-N-methylacrylamide 
• 893751-08-1 methyl 2-(4-fluorophenyl)cyclopropane-1-carboxylate 
• 459-32-5 (E)-4-fluorocinnamic acid 
• 96426-60-7 methyl (2E)-3-(4-fluorophenyl)-2-propenoate 
• 113903-98-3 tert-butyl 4-fluorocinnamate 
• 459-57-4 4-fluorobenzaldehyde 
• 459-32-5 4-fluorocinnamic acid 
• 301861-15-4 (+/-)-cis-2-(4-fluorophenyl)cyclopropanecarbonitrile 

Downstream Products

• 161711-27-9 (1R,2R)-2-(4-fluorophenyl)cyclopropanecarboxylic acid 
• 1414775-42-0 (1R,2R)-2-(4-fluorophenyl)cyclopropanecarboxylic acid [(R)-cyclopropyl-(3-ethanesulfonylphenyl)methyl](6-trifluoromethylpyridin-3-ylmethyl)amide 
• 1414775-44-2 (1R,2R)-2-(4-fluorophenyl)cyclopropanecarboxylic acid [(S)-cyclopropyl-(3-ethanesulfonylphenyl)methyl](6-trifluoromethylpyridin-3-ylmethyl)amide 
• 515179-19-8 (+)-(1S,2S)-2-(4-fluorophenyl)cyclopropanecarboxylic acid 
• 1314323-96-0 (1R,2S)-tert-butyl 2-(4-fluorophenyl)cyclopropylcarbamate 
• 113516-71-5 (1R,2S)-2-(4-fluorophenyl)cyclopropan-1-amine 
• 1609030-98-9 2-(4-fluorophenyl)-N-(2-(2-methyl-1H-indol-1-yl)ethyl)cyclopropane-1-carboxamide 

Relevant articles and documents

Co(II)-salen catalyzed stereoselective cyclopropanation of fluorinated styrenes

Three cis-selective Co(II)-salen complexes have been developed for the asymmetric cyclopropanation of para-fluorinated styrenes with ethyl diazoacetate. Increasing the steric reach of the C2-symmetric ligand side chains improved the enantiomeric ratio of the reaction from 28:1 to 66:1. The methodology was exemplified by the gram-scale synthesis of a lead compound for the treatment of castration-resistant prostate cancer (CRPC), as well as a structurally related analog.

PdII-Catalyzed Enantioselective C(sp3)?H Activation/Cross-Coupling Reactions of Free Carboxylic Acids

PdII-catalyzed enantioselective C(sp3)?H cross-coupling of free carboxylic acids with organoborons has been realized using either mono-protected amino acid (MPAA) ligands or mono-protected aminoethyl amine (MPAAM) ligands. A diverse range of aryl- and vinyl-boron reagents can be used as coupling partners to provide chiral carboxylic acids. This reaction provides an alternative approach to the enantioselective synthesis of cyclopropanecarboxylic acids and cyclobutanecarboxylic acids containing α-chiral tertiary and quaternary stereocenters. The utility of this reaction was further demonstrated by converting the carboxylic acid into cyclopropyl amine without loss of optical activity.

Synthesis and in vitro evaluation of novel N-cycloalkylcarbamates as potential cholinesterase inhibitors

Abstract: This present paper describes the preparation and characterization of a series of O-substituted N-cycloalkylcarbamate derivatives. These compounds were tested as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). All studied carbamates exhibited moderate inhibitory activity of both cholinesterases with values of IC50 in the range of 36.1–78.6?μM for AChE and 9.8–215.4?μM for BChE, respectively. These values are comparable with those values of inhibition obtained with the established drug rivastigmine. The cytotoxicity of all carbamates was evaluated using standard in vitro test with Jurkat cells. Many of the studied carbamates can be considered as promising compounds for potential medicinal applications with regard to their inhibitory activity as well as negligible cytotoxicity.