Ethyl bromodifluoroacetate

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
CAS Number	667-27-6[1] ;
3D model (JSmol)	Interactive image;
ChemSpider	62789;
ECHA InfoCard	100.010.517
EC Number	211-567-0;
PubChem CID	69585;
UNII	2QFZ6JJ5YH ;
CompTox Dashboard (EPA)	DTXSID40216845 ;
	InChI 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;
	SMILES BrC(Br)(F)C(=O)OCC;
Properties
Chemical formula	C4H5BrF2O2
Molar mass	202.983 g·mol−1
Appearance	clear 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:
Pictograms
Signal word	Danger
Hazard statements	H225, H314
Precautionary statements	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). Infobox references

Ethyl bromodifluoroacetate is an ester that can be used to introduce the CF₂ group when synthesising chemical compounds. It is a clear to yellow liquid. It is an ester of bromodifluoroacetic acid and ethyl alcohol.

Formation

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

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

datasheet, Santa Cruz Biotechnology, 2012
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.

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[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.