2,2-Difluorocyclopropanecarboxylic acid
CAS Number 107873-03-0
Chemistry Building Blocks, Fluorinated Building Blocks, Materials, Monomers, Non-Heterocyclic Building Blocks
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
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 | Tm = 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.