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Product Code B2561-1g
Price £90 ex. VAT

A gem-fluorinated cyclopropanecarboxylic acid building block

Used as a synthesis intermediate for APIs

Specifications | MSDS | Literature and Reviews

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

Multiple functional groups

For facile synthesis

Fluorinated building block

Fluorinated cyclopropane building block

For organic synthesis, medicinal chemistry and biochemistry research

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High purity 107873-03-0

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

2,2-Difluorocyclopropanecarboxylic acid chemical structure, CAS 107873-03-0.
2,2-Difluorocyclopropanecarboxylic acid chemical structure, CAS 107873-03-0

Product Details

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

MSDS Documentation

2,2-Difluorocyclopropanecarboxylic acid MSDS Sheet2,2-Difluorocyclopropanecarboxylic acid MSDS Sheet

Literature and Reviews

  1. 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.
  2. 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.
  3. 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.
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