127199-14-8

Basic information

• Product Name: (1S,2S)-2-Fluorocyclopropanecarboxylic acid
• Synonyms: Cyclopropanecarboxylic acid, 2-fluoro-, (1S,2S)-;(1S,2S)-2-FLUOROCYCLOPROPANECARBOXYLIC ACID(WX900028);(cis)-2-fluorocyclopropanecarboxylic acid Relative stereochemistry
• CAS NO: 127199-14-8
• Molecular Formula: C₄H₅FO₂
• Molecular Weight: 104.0797032
• Product Categories: organic building block
• Mol File: 127199-14-8.mol
• Article Data: 9

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: (1S,2S)-2-Fluorocyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-2-Fluorocyclopropanecarboxylic acid(127199-14-8)
• EPA Substance Registry System: (1S,2S)-2-Fluorocyclopropanecarboxylic acid(127199-14-8)

Safety Data

• Hazardous Substances Data: 127199-14-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1S,2S)-2-Fluorocyclopropanecarboxylic acid serves as a valuable building block in organic synthesis, enabling the creation of a wide range of biologically active compounds. Its distinct structure allows for the development of novel molecules with specific properties and functions.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (1S,2S)-2-Fluorocyclopropanecarboxylic acid is utilized as a key intermediate for the preparation of various drugs and pharmaceuticals. Its unique configuration and functional groups make it an attractive candidate for the design and synthesis of new medicinal agents with improved therapeutic profiles.
Used in Medicinal Chemistry:
(1S,2S)-2-Fluorocyclopropanecarboxylic acid is a valuable tool in medicinal chemistry, facilitating the development of innovative drugs and pharmaceuticals. Its chiral nature and functional groups contribute to the exploration of novel chemical space and the optimization of drug candidates for enhanced efficacy and selectivity.

Upstream product

• 154001-42-0 C₄H₅FO₂*C₁₅H₁₇N 
• 216872-00-3 (1R,2R)-2-Fluoro-cyclopropanecarboxylic acid propyl ester 
• 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 
• 177564-59-9 (1S,2S)-2-Fluoro-cyclopropanecarboxylic acid propyl ester 
• 177933-51-6 (1S,2S)-2-Fluorocyclopropanecarboxylic Acid Ethyl Ester 
• 188428-48-0 cis-ethyl 2-fluorocyclopropanecarboxylate 
• 127199-12-6 (1S,2S)-2-Fluoro-cyclopropanecarboxylic acid ((R)-1-phenyl-ethyl)-amide 
• 152237-14-4 tert-butyl 2-fluoro-cyclopropane-1-carboxylate 
• 137081-42-6 2-chloro-2-fluorocyclopropane carboxylic acid 

Downstream Products

• 185225-82-5 (1R,2S)-2-fluorocyclopropane carbonyl chloride 
• 127199-16-0 tert-butyl N-<(1R,2S)-2-fluorocyclopropyl>carbamate 
• 169884-67-7 (rac-(1R,2S)-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

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

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.).

(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.

Fluorinated cyclopropanecarboxylic acids and their derivatives

The addition of halofluorocarbenes such as :CF2, :CClF or :CBrF, generated from the appropriate halofluoromethanes with bases, to butadiene or isoprene gives the corresponding l-vinyl substituted halofluorocyclopropanes in moderate to good yield. The vinyl group facilitates the carbene addition and permits a subsequent wide derivatisation. Several transformations including hydroboration, oxidation and Curtius degradation are presented. Furthermore, replacement of the chlorine atom in 2-chloro-2-fluorocyclopropanecarboxylic acid derivatives by hydrogen is achieved catalytically with Raney nickel. This sequence provides a convenient route to mono-fluorine substituted cyclopropane carboxylic acids.