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Sigma-Aldrich

Chloroacetyl chloride

purum, ≥99.0% (GC)

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:
329752357
NACRES:
NA.22

vapor density

3.9 (vs air)

Quality Level

200

vapor pressure

60 mmHg ( 41.5 °C)

grade

purum

Assay

≥99.0% (GC)

form

liquid

refractive index

n20/D 1.453 (lit.)
n20/D 1.453

bp

105-106 °C (lit.)

mp

−22 °C (lit.)

solubility

water: insoluble

density

1.419 g/mL at 20 °C
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 an aliphatic acid chloride.

Application

Chloroacetyl chloride may be used to prepare:
  • 2-chloro-N-(pyridine-2-yl)acetamide via N-acylation of pyridin-2-amine
  • chloroacetyl cellulose by reacting with cellulose in N,N-dimethylformamide
  • azetobenzothiazine derivatives by reacting with 1,3-benzothiazines in the presence of a base in refluxing toluene
  • 2-chloro-1-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-ethanones by reacting with 3,5-diaryl-4,5-dihydropyrazoles
  • chloroacetyl isatins by reacting with isatins under microwave conditions
It acts as a linker during the grafting of pyrimethanil with chitosan.
Chloroacetyl chloride was used in the synthesis of N-hydrazino acetyl-sulphonamides.

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL3954
BCCL2184
BCCK9665
BCCK6014
BCCG2826

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Synthesis and Anticancer Activity of Isatin-Based Pyrazolines and Thiazolidines Conjugates.
Havrylyuk D, et al.
Arch. Pharm. (Weinheim), 344(8), 514-522 (2011)
Application of microwave induced Delepine reaction to the facile one pot synthesis of 7-substituted 1, 3-dihydro-2h-[1, 4]-benzodiazepin-2-one-5-methyl carboxylates from the corresponding 1-chloroacetyl isatins.
Sharma P, et al.
International Journal of Chemical Sciences, 8(1) (2010)
Oana Maria Parasca et al.
Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi, 117(1), 238-243 (2014-02-11)
Infections caused by bacterial species are common in immunocompromised patients and carry significant treatment costs and mortality. The emerging resistance of microorganisms to some synthetic antimicrobial agents makes it necessary to continue the research for new antimicrobial drugs. To design
Amination and thiolation of chloroacetyl cellulose through reactive dissolution in N, N-dimethylformamide.
Labafzadeh SR, et al.
Carbohydrate Polymers, 116, 60-66 (2015)
A Facial Protocol for the Synthesis of Benzofuran Derivatives by the Reaction of o-Hydroxy Aryl Ketone, Amine and Chloroacetyl Chloride.
Xia S, et al.
Bull. Korean Chem. Soc., 35(6), 1743-1743 (2014)
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