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469599

Sigma-Aldrich

Ethyl chlorodifluoroacetate

98%

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About This Item

Linear Formula:
ClCF2CO2C2H5
CAS Number:
383-62-0
Molecular Weight:
158.53
EC Number:
206-850-0
MDL number:
MFCD00013662
UNSPSC Code:
12352100
PubChem Substance ID:
24870471
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.358 (lit.)

bp

96-97.5 °C (lit.)

density

1.252 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C(F)(F)Cl

InChI

1S/C4H5ClF2O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3

InChI key

GVCAWQUJCHZRCB-UHFFFAOYSA-N

General description

Ethyl chlorodifluoroacetate (ECDFA) undergoes Reformatskii reaction with various aldehydes in DMF. It reacts with phenylacetylene to afford ethyl α,α−difluoro-4-phenyl-3-butenoates.

Application

Ethyl chlorodifluoroacetate (ECDFA) may be used as a starting reagent in the synthesis of 3-gem-difluoro-2-ethoxy allylic alcohols.

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H225,H314

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

64.4 °F - closed cup

Flash Point(C)

18 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

JAN Code

469599-100ML:
469599-VAR:
469599-BULK:
469599-25ML:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Fluorine-containing organozinc reagents. IV.: Reformatskii-type reactions of chlorodifluoroacet1c acid derivatives.
Lang RW and Schaub B.
Tetrahedron Letters, 29(24), 2943-2946 (1988)
A theoretical investigation on the kinetics and reactivity of the gas-phase reactions of ethyl chlorodifluoroacetate with OH radical and Cl atom at 298 K.
Mishra BK, et al.
Structural Chemistry, 25(2), 463-470 (2014)
Synthesis of 3-gem-difluoro-2-ethoxy allylic alcohols from ethyl chlorodifluoroacetate.
Begue J-P, et al.
Tetrahedron Letters, 35(3), 6097-6100 (1994)
Wadih Ghattas et al.
The Journal of organic chemistry, 71(22), 8618-8621 (2006-10-27)
An efficient preparation of pure ethyl Z- and E-alpha,alpha-difluoro-4-phenyl-3-butenoate 1a and 1b together with the corresponding acids 2a and 2b is described. The procedures involve stereocontrolled additions of *CF2CO2Et to phenylacetylene or beta-bromostyrene. Compound 1a is easily obtained by addition

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