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295795

Sigma-Aldrich

Ethyl bromodifluoroacetate

98%

Synonym(s):

2-Bromo-2,2-difluoroacetic acid ethyl ester, Bromodifluoroacetic acid ethyl ester, Ethyl 2-bromo-2,2-difluoroacetate, Ethyl 2-bromo-2,2-difluoroethaneperoxoate, Ethyl difluorobromoacetate

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About This Item

Linear Formula:
BrCF2COOCH2CH3
CAS Number:
667-27-6
Molecular Weight:
202.98
Beilstein:
1906095
EC Number:
211-567-0
MDL number:
MFCD00042069
UNSPSC Code:
12352100
PubChem Substance ID:
24857811
NACRES:
NA.22

Quality Level

200

Assay

98%

refractive index

n20/D 1.387 (lit.)

bp

112 °C/700 mmHg (lit.)

density

1.583 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C(F)(F)Br

InChI

1S/C4H5BrF2O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3

InChI key

IRSJDVYTJUCXRV-UHFFFAOYSA-N

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Related Categories

Application

Ethyl bromodifluoroacetate has been used in the preparation of:
  • substituted ethyl 2′-pyridyldifluoroacetates
  • 4-alkoxymethyl- and 4-aryloxymethyl-3,3-difluoropiperidines
  • α,α-difluoro-β-lactams
  • mono- and difluoromethylated phenanthridine derivatives

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H225 - H314

Hazard Classifications

Flam. Liq. 2 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

69.8 °F - closed cup

Flash Point(C)

21 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

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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Atsushi Tarui et al.
Organic & biomolecular chemistry, 12(33), 6484-6489 (2014-07-16)
A practical and highly enantioselective Reformatsky reaction of ethyl bromodifluoroacetate with imines using a cheap and commercially available amino alcohol ligand is described. A variety of α,α-difluoro-β-lactams were obtained in up to 74% yield with high enantioselectivity in excess of
Riccardo Surmont et al.
The Journal of organic chemistry, 75(3), 929-932 (2010-01-07)
Synthetic strategies toward 4-substituted 3,3-difluoropiperidines were evaluated. 4-Alkoxymethyl- and 4-aryloxymethyl-3,3-difluoropiperidines were synthesized via 1,4-addition of ethyl bromodifluoroacetate to 3-substituted acrylonitriles in the presence of copper powder, followed by borane reduction of the cyano substituent, lactamization, and reduction of the lactam.
Xiaoyang Sun et al.
Organic letters, 16(11), 2938-2941 (2014-05-23)
A practical and unified strategy has been described for the preparation of mono- and difluoromethylated phenanthridine derivatives using a visible-light-promoted alkylation and decarboxylation sequence from biphenyl isocyanides with ethyl bromofluoroacetate (EBFA) or ethyl bromodifluoroacetate (EBDFA). These reactions could be carried
Copper-mediated reaction of 2-halopyridines with ethyl bromodifluoroacetate.
Ashwood MS, et al.
Tetrahedron Letters, 43(50), 9271-9273 (2002)

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