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295795

Sigma-Aldrich

Ethyl bromodifluoroacetate

98%

Sinonimo/i:

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

Formula condensata:
BrCF2COOCH2CH3
Numero CAS:
667-27-6
Peso molecolare:
202.98
Beilstein:
1906095
Numero CE:
211-567-0
Numero MDL:
MFCD00042069
Codice UNSPSC:
12352100
ID PubChem:
24857811
NACRES:
NA.22

Livello qualitativo

200

Saggio

98%

Indice di rifrazione

n20/D 1.387 (lit.)

P. eboll.

112 °C/700 mmHg (lit.)

Densità

1.583 g/mL at 25 °C (lit.)

Gruppo funzionale

bromo
ester
fluoro

Stringa SMILE

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

InChI

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

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Applicazioni

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

Pittogrammi

FlameCorrosion
GHS02,GHS05

Avvertenze

Danger

Indicazioni di pericolo

H225,H314

Classi di pericolo

Flam. Liq. 2 - Skin Corr. 1B

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

69.8 °F - closed cup

Punto d’infiammabilità (°C)

21 °C - closed cup

Dispositivi di protezione individuale

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificati d'analisi (COA)

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

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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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