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105-39-5 - Ethyl chloroacetate, 99% - Chloroacetic acid ethyl ester - A15554 - Alfa Aesar

A15554 Ethyl chloroacetate, 99%

CAS Number
105-39-5
Synonyms
Chloroacetic acid ethyl ester

Size Price ($) Quantity Availability
100g 16.29
500g 31.83
2500g 70.02
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Ethyl chloroacetate, 99%

MDL
MFCD00000932
EINECS
203-294-0

Chemical Properties

Formula
C4H7ClO2
Formula Weight
122.55
Melting point
-26°
Boiling Point
142-144°
Flash Point
54°(149°F)
Density
1.159
Refractive Index
1.4210
Solubility
Soluble in water 20 g/L (20°C).

Applications

Ethyl chloroacetate is a reagent used in the preparation of 5 member heterocycles. It is used as pharmaceutical and organic intermediate. It is used as a solvent for organic synthesis.

Notes

Incompatible with acids, bases, oxidizing agents, reducing agents.

Literature References

J Q Liu, T Kurihara; M Miyagi; S Tsunasawa; M Nishihara; N Esaki; K Soda. Paracatalytic inactivation of L-2-haloacid dehalogenase from Pseudomonas sp. YL by hydroxylamine. Evidence for the formation of an ester intermediate. Journal of Biological Chemistry. 1997, 272 (6), 3363-3368.

Andrew J Moad; Lee J Klein; Dennis G Peters; Jonathan A Karty; James P Reilly. Catalytic reduction of ethyl chloroacetate by cobalt(I) salophen electrogenerated at vitreous carbon cathodes. Journal of Electroanalytical Chemistry. 2002, 531, (2), 163-169.

For examples of use in the Darzens reaction with carbonyl compounds to give glycidic esters, see: Org. Synth. Coll., 3, 727 (1955); 4, 459 (1963); reviews: Org. React., 5, 413 (1949); Chem. Rev., 55, 283 (1955). In the presence of base, glycidic esters rearrange to ɑ-substituted aldehydes: Org. Synth. Coll., 3, 733 (1955):

For a theoretical study of a proposed cyclic transition state in the Darzens reaction, see: J. Org. Chem., 61, 6723 (1996).

Undergoes phase-transfer catalyzed carbene-like addition to activated alkenes to give cyclopropane derivatives: Synth. Commun., 22, 1651 (1992):

Compare (±)-2-Chloropropionic acid, A12860, for a similar reaction.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H311-H331-H226-H400

Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Flammable liquid and vapour. Very toxic to aquatic life.

Precautionary Statements: P210-P261-P273-P280-P301+P310-P303+P361+P353-P361-P304+P340-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,3783
Beilstein
506455
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2915.40
TSCA
Yes
RTECS
AF9110000

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