167073-07-6

Basic information

• Product Name: Cyclopropanecarboxylic acid, 2-fluoro-, (1S,2R)-
• Synonyms: Cyclopropanecarboxylic acid, 2-fluoro-, (1S,2R)-;(1S,2R)-2-fluorocyclopropane-1-carboxylic acid
• CAS NO: 167073-07-6
• Molecular Formula: C4H5FO2
• Molecular Weight: 104.0797032
• Mol File: 167073-07-6.mol

Chemical Properties

• Boiling Point: 202.3±33.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• PKA: 4.00±0.11(Predicted)
• CAS DataBase Reference: Cyclopropanecarboxylic acid, 2-fluoro-, (1S,2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarboxylic acid, 2-fluoro-, (1S,2R)-(167073-07-6)
• EPA Substance Registry System: Cyclopropanecarboxylic acid, 2-fluoro-, (1S,2R)-(167073-07-6)

Safety Data

• Hazardous Substances Data: 167073-07-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Cyclopropanecarboxylic acid, 2-fluoro-, (1S,2R)is utilized as a key intermediate in the synthesis of pharmaceutical compounds. Its unique structural features and stereochemistry make it a valuable building block for the development of new drugs with specific therapeutic targets.
Used in Organic Synthesis:
Cyclopropanecarboxylic acid, 2-fluoro-, (1S,2R)serves as a versatile reagent in organic synthesis, enabling the creation of a variety of complex organic molecules. Its fluorinated cyclopropane ring and carboxylic acid functionality can be exploited in various synthetic routes, facilitating the formation of diverse chemical products.
Used in Chemical Industries:
Cyclopropanecarboxylic acid, 2-fluoro-, (1S,2R)may be employed in the chemical industry for the production of specialty chemicals, agrochemicals, and other fine chemicals. Its unique properties and reactivity can contribute to the development of innovative products and processes within these sectors.

Upstream product

• 152237-14-4 tert-butyl 2-fluoro-cyclopropane-1-carboxylate 
• 216872-00-3 (1R,2R)-2-Fluoro-cyclopropanecarboxylic acid propyl ester 
• 188428-48-0 cis-ethyl 2-fluorocyclopropanecarboxylate 
• 127199-12-6 (1S,2S)-2-Fluoro-cyclopropanecarboxylic acid ((R)-1-phenyl-ethyl)-amide 
• 127199-12-6 (1R,2R)-2-Fluoro-cyclopropanecarboxylic acid ((R)-1-phenyl-ethyl)-amide 
• 107-15-3 ethylenediamine 
• 137081-42-6 2-chloro-2-fluorocyclopropane carboxylic acid 
• 152237-14-4 trans-t-butyl-2-fluorocyclopropane-1-carboxylate 
• 152237-14-4 cis-t-butyl-2-fluorocyclopropane-1-carboxylate 
• 154001-42-0 C₄H₅FO₂*C₁₅H₁₇N 
• 216872-25-2 (1S,2S)-2-Fluoro-cyclopropanecarboxylic acid hexyl ester 
• 177564-60-2 (1S,2S)-2-Fluoro-cyclopropanecarboxylic acid pentyl ester 
• 161582-46-3 (1R,2R)-2-Fluoro-cyclopropanecarboxylic acid butyl ester 
• 161582-46-3 (1S,2S)-2-Fluoro-cyclopropanecarboxylic acid butyl ester 

Downstream Products

• 169884-67-7 ((1R,2S)-2-fluorocyclopropyl)methanol 
• 169884-67-7 (rac-(1R,2R)-2-fluorocyclopropyl)methanol 
• 185225-82-5 (±)-cis-2- fluorocyclopropanecarbonyl chloride 
• 1258293-96-7 2,6-dichloro-N-(2-((1S,2S)-2-fluorocyclopropanecarboxamido)pyridin-4-yl)-benzamide 
• 1258293-95-6 2,6-dichloro-N-(2-((1R,2R)-2-fluorocyclopropanecarboxamido)pyridin-4-yl)benzamide 
• 185225-82-5 (1R,2S)-2-fluorocyclopropane carbonyl chloride 
• 185225-82-5 cis-2-fluorocyclopropanoyl chloride 
• 169884-67-7 [(1R,2R)-2-fluorocyclopropyl]methanol 

Relevant articles and documents

Novel process for synthesizing 2 -fluorocyclopropylamine with high selectivity and asymmetric synthesis

A novel highly selective asymmetric synthesis process of 2 -fluorocyclopropylamine (Structural I). The method provided by the invention uses 1 - fluorine -1 - benzene (propylene) sulfonyl methane and chiral epichlorohydrin to construct chiral cyclopropane under basic conditions, and a new synthetic route not only achieves a special cis-trans selectivity, but also has a highly specific stereoselectivity. The synthesis route is efficient, the reaction condition is mild, the method is suitable for large industrial production in a green environment, 2 -fluorocyclopropylamine production cost is greatly reduced.

Novel method for asymmetric synthesis of (1S,2S)-2-fluorocyclopropanecarboxylic acid under catalysis of chiral rhodium catalyst

The invention provides a novel method for asymmetric synthesis of (1S, 2S)-2-fluorocyclopropanecarboxylic acid under catalysis of a chiral rhodium catalyst. The chiral rhodium catalyst not only can catalyze 1-fluoro-1-benzenesulfonyl ethylene and ethyl di

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Novel 2-fluorocyclopropane carboxylic acid synthesis method

The invention discloses a novel 2-fluorocyclopropane carboxylic acid synthesis method. The novel 2-fluorocyclopropane carboxylic acid synthesis method comprises the following steps: 1) enabling 1,1-dichloro-1-fluoroethane and thiophenol to react under the action of alkali to produce a phenyl sulfide intermediate; 2) implementing an oxidizing reaction between the phenyl sulfide intermediate and Oxone; 3) implementing an elimination reaction on an obtained product under the action of alkali to obtain 1-fluorine-1-phenylsulfonyl ethane; 4) implementing an addition reaction on the 1-fluorine-1-phenylsulfonyl ethane and ethyl diazoacetate under the action of a catalyst to obtain a cyclopropane intermediate; 5) implementing an elimination reaction on the cyclopropane intermediate under the action of alkali, and then acidifying to obtain 2-fluorocyclopropane carboxylic acid. The synthetic route is short, the materials are bulk commodities, cheap and easy to get, the Oxone replaces a commonly used mCPBA agent, the process is safely amplified, the reaction yield is increased, the production cost is greatly lowered, and the operation is simple.

Stereoselective synthesis of cis -2-fluorocyclopropanecarboxylic acid

A rhodium-catalyzed cyclopropanation of 1-fluoro-1-(phenylsulfonyl)ethylene and diazo esters is described as an effective method for the stereoselective synthesis of cis-2-fluorocyclopropanecarboxylic acid. This process provides an example of the cyclopro

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.

PROCESS FOR REDUCTIVE DEHALOGENATION

A method ofproducing2-fluorocyclopropane-1-carboxylic acid ester, which comprise by allowing a compound represented by the following formula (1): wherein X represents a chlorine atom, a bromine atom or an iodine atom; and R1 represents an alkyl

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There is disclosed a process process for producing a cyclopropanecarboxylate of formula (1): 1which process comprises reacting cyclopropanecarboxylic acid of formula (2): 2with a monohydroxy compound of formula (3): R6OH??(3),in the presence of a catalyst compound comprising an element of to Group 4 of the Periodic Table of Elements.

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.

Resolution of cis-2-fluorocyclopropanecarboxylic acid by a microbial enantioselective hydrolysis

The important key intermediate of quinolone analogue synthesis, (1S,2S)- 2-fluorocyclopropanecarboxylic acid, was prepared enantioselectively by a microbial resolution. One of the strains with the highest enzymatic specificity was selected from soil and when lyophilized cells were treated with corresponding ester, the remaining (1S,2S)-ester was obtained with high enantiomeric purity (98% e.e.).