127199-13-7

Basic information

• Product Name: (1R,2R)-2-fluorocyclopropanecarboxylic acid
• Synonyms: (1R,2R)-2-fluorocyclopropanecarboxylic acid;(1R,2R)-(-)-cis-2-Fluorocyclopropanecarboxylic acid;(1R,2R)-2-fluorocyclopropanecarboxylic;(1R,2R)-2-Fluorocyclopropane-1-carboxylic acid;(1R,2R)-2-fluorocyclopropanecarboxylic acid(WXFC0571)
• CAS NO: 127199-13-7
• Molecular Formula: C₄H₅FO₂
• Molecular Weight: 104.0797032
• EINECS: -0
• Product Categories: organic building block
• Mol File: 127199-13-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 202.3±33.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.78±0.20(Predicted)
• CAS DataBase Reference: (1R,2R)-2-fluorocyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-2-fluorocyclopropanecarboxylic acid(127199-13-7)
• EPA Substance Registry System: (1R,2R)-2-fluorocyclopropanecarboxylic acid(127199-13-7)

Safety Data

• Safety Statements: 24/25
• RIDADR: UN1993
• Hazardous Substances Data: 127199-13-7(Hazardous Substances Data)

Usage

General Description

(1R,2R)-2-fluorocyclopropanecarboxylic acid is a small organic compound with the chemical formula C4H5FO2. It is a fluorinated cyclopropane derivative, and its structure consists of a three-membered cyclopropane ring with a carboxylic acid functional group and a fluorine atom attached to one of the carbon atoms in the ring. (1R,2R)-2-fluorocyclopropanecarboxylic acid is used in organic synthesis and drug development as a building block for more complex molecules. Its unique structure and chemical properties make it an important tool for creating new compounds with potential biological and pharmaceutical activities.

InChI:InChI=1S/C4H5FO2/c5-3-1-2(3)4(6)7/h2-3H,1H2,(H,6,7)/t2-,3+/m0/s1

Upstream product

• 161582-46-3 (1R,2R)-2-Fluoro-cyclopropanecarboxylic acid butyl ester 
• 216872-00-3 (1R,2R)-2-Fluoro-cyclopropanecarboxylic acid propyl ester 
• 152237-14-4 tert-butyl 2-fluoro-cyclopropane-1-carboxylate 
• 137081-42-6 2-chloro-2-fluorocyclopropane carboxylic acid 
• 127199-12-6 (1R,2R)-2-Fluoro-cyclopropanecarboxylic acid ((R)-1-phenyl-ethyl)-amide 
• 188428-48-0 cis-ethyl 2-fluorocyclopropanecarboxylate 

Downstream Products

• 127199-12-6 2-Fluoro-cyclopropanecarboxylic acid ((R)-1-phenyl-ethyl)-amide 
• 167073-09-8 tert-butyl N-[(1S,2R)-2-fluorocyclopropyl]carbamate 
• 169884-67-7 (rac-(1R,2S)-2-fluorocyclopropyl)methanol 
• 185225-82-5 cis-2-fluorocyclopropanoyl chloride 
• 169884-67-7 [(1R,2R)-2-fluorocyclopropyl]methanol 
• 185225-82-5 (±)-trans-2-fluorocyclopropanecarbonyl chloride 

Relevant articles and documents

Purification, properties and reactivity of the esterase from Micrococcus sp.

The esterase from Micrococcus sp., which hydrolyzes n-propyl-2- fluorocyclopropanecarboxylate (3) enantioselectively, was highly purified by three types of chromatography. The purified enzyme was inactivated by Hg and diisopropyl fluorophosphate (DFP). It was a monomer with a molecular weight of about 35000. The enzyme exhibits esterase activity towards many aliphatic propyl esters. The enantioselectivity for substrate (3) using purified enzyme did not differ from that of crude enzyme.

PROCESS FOR PRODUCING 1,2-CIS-2-FLUOROCYCLOPROPANE-1-CARBOXYLIC ESTER COMPOUND

Provided is an industrially applicable process for producing 1,2-cis-2-fluorocyclopropane-1-carboxylic ester. A process for producing a compound represented by formula (3): [wherein R 1 represents, for example, a C1-C8 alkyl group], which process includes reacting a compound represented by formula (1) : [wherein X 1 represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom; X 2 represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom; X 1 and X 2 are not simultaneously hydrogen atoms; and R 1 has the same meaning as defined in formula (3)] with a reducing agent represented by formula (2): €?€?€?€?€?€?€?€?M 1 BH m R 2 n (2-1) or M 2 (BH m R 2 n ) 2 €?€?€?€?€?(2-2) [wherein M 1 represents an alkali metal atom; M 2 represents an alkaline earth metal atom or a zinc atom; R 2 represents, for example, a hydrogen atom; m represents an integer from 1 to 4; n represents an integer from 0 to 3; and the sum of m and n is 4] in the presence of an aprotic polar solvent, and a Lewis acid such as a halide of an atom selected from among, for example, boron, magnesium, and aluminum.

(Fluorocyclopropyl)quinolones. 2. Synthesis and stereochemical structure- activity relationships of chiral 7-(7-amino-5-azaspiro[2.4]heptan-5-yl)-1- (2-fluorocyclopropyl)quinolone antibacterial agents

A series of novel chiral 7-(7-amino-5-azaspiro[2.4]heptan-5-yl)-8-chloro- 1-(2-fluorocyclopropyl)-quinolones were synthesized as a continuation of a research project of 1-(2-fluorocyclopropyl)-quinolones by considering stereochemical and physicochemical properties of the molecule. Absolute configurations of the 1-(cis-2-fluorocyclopropyl) moiety and the 7-(7-amino- 5-azaspiro-[2.4]heptan-5-yl) moiety were determined by X-ray crystallographic analysis. Stereochemical structure-activity relationship studies indicated that 1-[(1R,2S)-2-fluorocyclopropyl] and 7-[(7S)-amino-5-azaspiro[2.4]heptan- 5-yl] derivatives are more potent against Gram-positive and Gram-negative bacteria than the other stereoisomers and 7-[(7S)-7-amino-5-azaspiro[2.4]- heptan-5-yl]-8-chloro-1-[(1R,2S)-2-fluorocyclopropyl]quinolone (33) is the most potent of all stereoisomers. Pharmacokinetic profiles and physicochemical properties of the selected compounds were also examined, and it was found that 33 (DU-6859a) possesses moderate lipophilicity and good pharmacokinetic profiles.