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295795

Sigma-Aldrich

Ethyl bromodifluoroacetate

98%

Linear Formula:
BrCF2COOCH2CH3
CAS Number:
Molecular Weight:
202.98
Beilstein:
1906095
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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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

Packaging

5 g in glass bottle

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

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

Certificate of Analysis

Certificate of Origin

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

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