105919-34-4

Usage

Uses

Used in Pharmaceutical Synthesis:
(1S,2S)-2-fluorocyclopropanecarboxylic acid is utilized as a key building block in the synthesis of various pharmaceuticals, particularly those with potential antibacterial or antifungal properties. Its unique structure and fluorination contribute to the development of new drugs with enhanced efficacy and selectivity.
Used in Organic Compound Production:
(1S,2S)-2-fluorocyclopropanecarboxylic acid is also employed in the production of certain organic compounds, where its specific structural features and reactivity can be leveraged to create novel molecules with desired properties.
Used as a Reagent in Chemical Reactions:
(1S,2S)-2-fluorocyclopropanecarboxylic acid serves as a reagent in various chemical reactions, facilitating the synthesis of complex molecules and aiding in the development of new chemical processes.
Used in Chiral Drug Synthesis:
Due to its two stereocenters, (1S,2S)-2-fluorocyclopropanecarboxylic acid is a valuable chiral building block for the synthesis of chiral drugs and bioactive compounds. Its stereochemistry allows for the creation of enantiomerically pure substances, which is crucial for the development of drugs with specific therapeutic effects and reduced side effects.

Upstream product

• 137081-42-6 2-chloro-2-fluorocyclopropane carboxylic acid 
• 152237-14-4 tert-butyl 2-fluoro-cyclopropane-1-carboxylate 

Downstream Products

• 127199-12-6 2-Fluoro-cyclopropanecarboxylic acid ((R)-1-phenyl-ethyl)-amide 
• 185225-82-5 (±)-trans-2-fluorocyclopropanecarbonyl chloride 
• 169884-67-7 (rac-(1R,2S)-2-fluorocyclopropyl)methanol 

Relevant academic research and scientific papers

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.

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.