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Merck
CN

22880

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
329752357
EC Number:
201-171-6
Beilstein/REAXYS Number:
605439
MDL number:
MFCD00000725
Assay:
≥99.0% (GC)
Form:
liquid

Key Documents

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InChI key

VGCXGMAHQTYDJK-UHFFFAOYSA-N

InChI

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

SMILES string

ClCC(Cl)=O

vapor density

3.9 (vs air)

vapor pressure

60 mmHg ( 41.5 °C)

grade

purum

assay

≥99.0% (GC)

form

liquid

Quality Level

200

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.)

functional group

acyl chloride, chloro

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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.

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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

supp_hazards

EUH014,EUH029

Storage Class

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

ppe

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN9005
BCCN1627
BCCL3954
BCCL2184
BCCK9665

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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
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)
Amination and thiolation of chloroacetyl cellulose through reactive dissolution in N, N-dimethylformamide.
Labafzadeh SR, et al.
Carbohydrate Polymers, 116, 60-66 (2015)
Novel indole syntheses by ring transformation of ?-lactam-condensed 1, 3-benzothiazines into indolo [2, 3-b][1, 4] benzothiazepines and indolo [3, 2-c] isoquinolines.
Fodor L, et al.
Tetrahedron, 68(3), 851-856 (2012)
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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