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22880

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

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
BCCG2826
BCCG0544
BCCF1454
BCCD9626
BCCC6266

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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)
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)
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)
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)
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