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D152803

Sigma-Aldrich

Dimethylcarbamyl chloride

98%

Synonym(s):

Chloroformic acid dimethyl amide, Dimethylcarbamoyl chloride

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About This Item

Linear Formula:
(CH3)2NCOCl
CAS Number:
79-44-7
Molecular Weight:
107.54
Beilstein:
878197
EC Number:
201-208-6
MDL number:
MFCD00000635
UNSPSC Code:
12352100
PubChem Substance ID:
24893469
NACRES:
NA.22

Quality Level

200

Assay

98%

form

liquid

refractive index

n20/D 1.453 (lit.)

bp

167-168 °C/775 mmHg (lit.)

mp

−33 °C (lit.)

density

1.168 g/mL at 25 °C (lit.)

SMILES string

CN(C)C(Cl)=O

InChI

1S/C3H6ClNO/c1-5(2)3(4)6/h1-2H3

InChI key

YIIMEMSDCNDGTB-UHFFFAOYSA-N

Application

Dimethylcarbamyl chloride can be used to synthesize:
  • Disubstituted carbamates from benzylphenols.
  • 2-Cyanoisonicotinamide by reacting with isonicotinic acid N-oxide and zinc cyanide. This method was adopted to synthesize a novel xanthine oxidoreductase inhibitor.
  • Acetylcholinesterase (AChE) and serotonin transporter (SERT) dual inhibitors.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

179.6 °F - closed cup

Flash Point(C)

82 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK1943
BCCJ9555
BCCJ7780
BCCJ7781
BCCJ1963

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Polypeptides. XII. The Optical Rotation and Configurational Stability of α-Helices1.
Blout E R, et al.
Journal of the American Chemical Society, 79(3), 749-750 (1957)
Zinc cyanide mediated direct α-cyanation of isonicotinic acid N-oxide. Application to the synthesis of FYX-051, a xanthine oxidoreductase inhibitor.
Huo Z, et al.
Tetrahedron Letters, ?49(28), 4369-4371 (2008)
Design and synthesis of dual inhibitors of acetylcholinesterase and serotonin transporter targeting potential agents for Alzheimer's disease.
Kogen H, et al.
Organic Letters, 4(20), 3359-3362 (2002)
A R Sellakumar et al.
Journal of environmental pathology and toxicology, 4(1), 107-115 (1980-08-01)
The comparative carcinogenicity of dimethylcarbamoyl chloride (DMCC) was studies in male, Syrian Golden Hamsters by inhalation. Hamsters were exposed to 1ppm and the exposure periods were 6 hours per day, 5 days per week for the lifetime of the animals.
A Segal et al.
Chemico-biological interactions, 40(2), 209-231 (1982-06-01)
The rodent carcinogens dimethylcarbamyl chloride (DMCC) and diethylcarbamyl chloride (DECC) react with dGuo (pH 7.0-7.5, 37 degrees C, 4 h) to form the O6-acyl derivatives 6-dimethylcarbamyloxy-2'-deoxyguanosine (6-DMC-dGuo) and 6-diethylcarbamyloxy-2'-deoxyguanosine (6-DEC-dGuo), respectively. Reaction of DMCC with dThd under identical conditions yielded
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