2,2-Difluorocyclopropanecarboxylic acid

CAS Number 107873-03-0

Chemistry Building Blocks, Fluorinated Building Blocks, Monomers, Non-Heterocyclic Building Blocks

2,2-Difluorocyclopropanecarboxylic acid MSDS

2,2-Difluorocyclopropanecarboxylic acid CAS 107873-03-0

A gem-fluorinated cyclopropanecarboxylic acid building block

Used as a synthesis intermediate for APIs

Overview
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2,2-Difluorocyclopropanecarboxylic acid (CAS number 107873-03-0) is a 3-membered ring substituted with two fluorines and a carboxylic acid. The inductive effect introduced by the gem-difluorination enhances the acidity of 2,2-difluorocyclopropanecarboxylic acid, compared to the non-fluorinated species. The carboxylic acid allows 2,2-difluorocyclopropanecarboxylic acid to be attached to molecular scaffolds through esterification. It can also undergo functional group conversion to form acyl halide, isocyanate and amine, for varied reactivities.

An unexpected ring-opening has been discovered while 2,2-difluorocyclopropanecarboxylic acid reacts with arenes in Friedel-Crafts reaction. It is proposed that the formation of the acylium ion destabilises the strained 3-membered ring leading to the ring-opening reaction.

Multiple functional groups

For facile synthesis

Fluorinated cyclopropane building block

For organic synthesis, medicinal chemistry and biochemistry research

Worldwide shipping

Quick and reliable shipping

High purity

>97% High purity

General Information

CAS Number	107873-03-0
Chemical Formula	C₄H₄F₂O₂
Full Name	2,2-Difluorocyclopropanecarboxylic acid
Molecular Weight	122.07 g/mol
Synonyms	2,2-Difluorocyclopropane-1-carboxylic Acid
Classification / Family	Fluorinated building blocks, Carboxylic acid building blocks, APIs

Chemical Structure

Product Details

Purity	97%
Melting Point	T_m = 60 °C – 65 °C
Appearance	Off-white powder

MSDS Documentation

2,2-Difluorocyclopropanecarboxylic acid MSDS Sheet

Literature and Reviews

Dual inhibition of TYK2 and JAK1 for the treatment of autoimmune diseases: discovery of ((S)-2,2-difluorocyclopropyl)((1R,5S)-3-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl)methanone (PF-06700841), A. Fensome et al., J. Med. Chem., 61(19), 8597–8612(2018); DOI: 10.1021/acs.jmedchem.8b00917.
Effect of gem-difluorination on the key physicochemical properties relevant to medicinal chemistry: the case of functionalized cycloalkanes, S. Holovach et al., Chem. Eur. J., 28(19), e202200331(2022); DOI: 10.1002/chem.202200331.
Friedel-Crafts reactions of 2,2-difluorocyclopropanecarbonyl chloride: unexpected ring-opening chemistry, W. Dolbier et al., J. Org. Chem., 76(9), 3450–3456(2011); DOI: 10.1021/jo200423y.
Synthesis of gem-difluoromethylene building blocks through regioselective allylation of gem-difluorocyclopropanes, D. Munemori et al., Org. Lett., 16(10), 2638–2641(2014); DOI: 10.1021/ol500803r.
The preparation and properties of 1,1-difluorocyclopropane derivatives, K. Adekenova et al., Beilstein J. Org. Chem., 17, 245–272(2021); DOI: 10.3762/bjoc.17.25.

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