Jump to content

Ethyl bromodifluoroacetate

From Wikipedia, the free encyclopedia
Ethyl bromodifluoroacetate
Names
IUPAC name
Ethyl 2-bromo-2,2-difluoroacetate
Systematic IUPAC name
Ethyl 2,2-dibromo-2-fluoro-acetate
Other names
Difluorobromoacetic acid ethyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.517 Edit this at Wikidata
EC Number
  • 211-567-0
UNII
  • InChI=1S/C4H5BrF2O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3
    Key: IRSJDVYTJUCXRV-UHFFFAOYSA-N
  • InChI=1/C4H5Br2FO2/c1-2-9-3(8)4(5,6)7/h2H2,1H3
  • BrC(Br)(F)C(=O)OCC
Properties
F2BrCHCO2CH2CH3
Molar mass 202.983 g·mol−1
Appearance Colorless to slightly yellow liquid
Density 1.583 g/mL
Boiling point 82 °C (180 °F; 355 K) pressure is at 33 torr
Vapor pressure 1.36 mmHg at 25°C
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H225, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ethyl bromodifluoroacetate is an ester with the chemical formula F2BrCH−CO2CH2CH3. It can be used to introduce the CF2 group when synthesising chemical compounds. It is a colorless to yellow liquid. It is an ethyl ester of bromodifluoroacetic acid.

Formation

[edit]

Ethyl fluorosulfonoxydifluoroacetate can react with sodium bromide (NaBr) to produce ethyl bromodifluoroacetate. And this reaction could happen in the solvent sulfolane. The reactions takes 12 hours at 100 °C with a yield of 31%.

Reactions

[edit]

Ethyl bromodifluoroacetate, and other similar compounds containing a CF2 units can be generated using the Reformatsky reagent with aldehydes and ketones. This yields 2,2-difluoro-3-hydroxy esters. Also ethyl bromdifluoroacetate is considered to be a good compound in generation of compounds and for testing with other organic compounds like lactones, imines and other amino acids.[2]

References

[edit]
  1. ^ datasheet, Santa Cruz Biotechnology, 2012
  2. ^ Sato, Kazuyuki; Tamura, Misato; Tamoto, Kei; Omote, Masaaki; Ando, Akira; Kumadaki, Itsumaro (2000). "Michael-type Reaction of Ethyl Bromodifluoroacetate with α,β-Unsaturated Carbonyl Compounds in the Presence of Copper Powder" (PDF). Chemical and Pharmaceutical Bulletin. 48 (7): 1023–1025. doi:10.1248/cpb.48.1023. PMID 10923834.