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104493

Sigma-Aldrich

Chloroacetyl chloride

98%

Synonym(s):

Chloroacetic chloride

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About This Item

Linear Formula:
ClCH2COCl
CAS Number:
79-04-9
Molecular Weight:
112.94
Beilstein:
605439
EC Number:
201-171-6
MDL number:
MFCD00000725
UNSPSC Code:
12352100
PubChem Substance ID:
24846647
NACRES:
NA.22

vapor density

3.9 (vs air)

vapor pressure

60 mmHg ( 41.5 °C)

Assay

98%

refractive index

n20/D 1.453 (lit.)

bp

105-106 °C (lit.)

mp

−22 °C (lit.)

density

1.418 g/mL at 25 °C (lit.)

SMILES string

ClCC(Cl)=O

InChI

1S/C2H2Cl2O/c3-1-2(4)5/h1H2

InChI key

VGCXGMAHQTYDJK-UHFFFAOYSA-N

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General description

Chloroacetyl chloride is used as a chlorinating agent, acylating agent, precursor to monochloroketene, and as a building block for cyclization.

Chloroacetyl chloride causes the acylation of cyano-pyrazoline during the synthesis of secondary amine-substituted cyano-pyrazoline derivatives.

Application

Chloroacetyl chloride can be used for chloroacetylation and chemical modification of poly(glycidyl methacrylate). Chloroacetyl chloride was used to study the in vitro metabolism of chloroacetamide herbicides by rat and human liver microsomes. Chloroacetyl chloride was used in the synthesis of some novel quinoline derivatives having antileishmanial activity.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Eye Dam. 1 - Skin Corr. 1A - STOT RE 1

Target Organs

Lungs

Supplementary Hazards

EUH014,EUH029

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

212.0 °F - closed cup

Flash Point(C)

100 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Chloroacetyl Chloride
George AO, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Jin Hee Ahn et al.
Bioorganic & medicinal chemistry letters, 14(17), 4461-4465 (2004-09-11)
A new series of cyano-pyrazoline derivatives with secondary amine at P-2 site was synthesized through achiral and chiral synthetic methods and evaluated for their ability to inhibit dipeptidyl peptidase IV (DP-IV). Compound 5i revealed good in vivo efficacy (ED50: 4.1
S Coleman et al.
Environmental health perspectives, 108(12), 1151-1157 (2001-01-03)
Acetochlor [2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamide], alachlor [N-(methoxymethyl)-2-chloro-N-(2, 6-diethyl-phenyl)acetamide], butachlor [N-(butoxymethyl)-2-chloro-N-(2,6-diethyl-phenyl)acetamide], and metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide] are pre-emergent herbicides used in the production of agricultural crops. These herbicides are carcinogenic in rats: acetochlor and alachlor cause tumors in the nasal turbinates, butachlor causes stomach tumors
Niranjan P Sahu et al.
Bioorganic & medicinal chemistry, 10(6), 1687-1693 (2002-04-09)
Some novel quinoline derivatives were prepared and tested for antileishmanial activity. 2-(2-Methylquinolin-4-ylamino)-N-phenylacetamide (2) was found to be significantly more active than the standard antileishmanial drug sodium antimony gluconate (SAG) in reducing the parasite load both in the spleen and liver
Kenawy el-R et al.
Journal of controlled release : official journal of the Controlled Release Society, 50(1-3), 145-152 (1998-08-01)
Polymers with antibacterial activity have been synthesized by chemical modification of poly(glycidyl methacrylate). The glycidyl methacrylate was polymerized by the free radical polymerization technique. The poly(glycidyl methacrylate) was hydrolyzed and was chloroacetylated using chloroacetyl chloride. The chloroacetylated product was modified
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