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Sigma-Aldrich

Difluoroacetic acid

98%

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Synonym(s):
1,1-Difluoroacetic acid, 2,2-Difluoroacetic acid
Linear Formula:
F2CHCO2H
CAS Number:
381-73-7
Molecular Weight:
96.03
Beilstein:
1098588
EC Number:
206-839-0
MDL number:
MFCD00004220
UNSPSC Code:
12352106
PubChem Substance ID:
24848539
NACRES:
NA.22

Quality Level

200

Assay

98%

form

liquid

refractive index

n20/D 1.344 (lit.)

bp

132-134 °C (lit.)

mp

−1 °C (lit.)

density

1.526 g/mL at 25 °C (lit.)

SMILES string

OC(=O)C(F)F

InChI

1S/C2H2F2O2/c3-1(4)2(5)6/h1H,(H,5,6)

InChI key

PBWZKZYHONABLN-UHFFFAOYSA-N

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General description

Difluoroaceticacid is a monocarboxylic acid and an organofluorine compound. Difluoroaceticacid is easy-to-handle reagent, useful for obtaining difluoromethyl substituents. Difluoroacetic acid can be used asdifluoromethylating reagent for the direct C−H difluoromethylation ofheteroaromatic compounds.

Application

Used in the preparation of 2-difluoromethylbenzimidazoles, -oxazoles and -thiazoles from ortho-substituted anilines mediated by triphenylphoshine.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H332,H412

Hazard Classifications

Acute Tox. 4 Inhalation - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1A

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Gaëlle Blond et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 8(13), 2917-2922 (2002-12-20)
Ethers of trifluoroacetaldehyde hemiaminals can undergo dehydrofluorination under basic conditions to provide ethers of difluoroketene hemiaminals. The latter behave as equivalents of difluoroacetamide or difluoroacetate anions towards various electrophiles, yielding a range of difluoromethylcarbonyl products.
Hoffman B M Lantum et al.
Toxicological sciences : an official journal of the Society of Toxicology, 70(2), 261-268 (2002-11-21)
Dichloroacetic acid (DCA), chlorofluoroacetic acid (CFA), and difluoroacetic acid (DFA) are inhibitors of pyruvate dehydrogenase kinase. DCA is used for the clinical management of congenital lactic acidosis. Glutathione transferase zeta (GSTZ1-1) catalyzes the biotransformation of DCA and CFA, and DCA
J M Dalstein et al.
Comptes rendus des seances de la Societe de biologie et de ses filiales, 174(5), 821-825 (1980-01-01)
In the anesthetized rat, the intraperitoneal injection of 40 mg/kg sodium difluoroacetate (DFA), an activator of the pyruvate dehydrogenase, counteracted the hyperlactatemia induced by a high dose of phenformin (40 mg/kg) injected concomitantly. In the normal conscious dog, the administration
J N Commandeur et al.
Biochemical pharmacology, 37(23), 4495-4504 (1988-12-01)
The biotransformation and the hepato- and nephrotoxicity of the mercapturic acids (N-acetyl-1-cysteine S-conjugates) of three structurally related 2,2-difluoroethylenes were investigated in vivo in the rat. All mercapturic acids appeared to cause nephrotoxicity, without any measureable effect on the liver. The
Difluoroacetic acid as a new reagent for direct C- H difluoromethylation of heteroaromatic compounds
Tung TT, et al.
Chemistry?A European Journal , 23(72), 18125-18128 (2017)
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