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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.)

functional group

bromo
ester
fluoro

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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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

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Certificates of Analysis (COA)

Lot/Batch Number
04511JJ
1400346
03318HJ
07619BJ
U18820

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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
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.
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
Copper-mediated reaction of 2-halopyridines with ethyl bromodifluoroacetate.
Ashwood MS, et al.
Tetrahedron Letters, 43(50), 9271-9273 (2002)

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