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D186252

Sigma-Aldrich

N,N-Dimethylsulfamoyl chloride

99%

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Synonym(s):
Dimethylamidosulfonyl chloride, Dimethylaminosulfonyl chloride, Dimethylsulphamoyl chloride, N,N-Dimethylamidosulfonyl chloride, N,N-Dimethylaminosulfonyl chloride, N,N-Dimethylsulfamoyl chloride, N,N-Dimethylsulfamyl chloride
Linear Formula:
(CH3)2NSO2Cl
CAS Number:
13360-57-1
Molecular Weight:
143.59
Beilstein:
741979
EC Number:
236-412-4
MDL number:
MFCD00007425
UNSPSC Code:
12352100
PubChem Substance ID:
24893558
NACRES:
NA.22

Quality Level

200

Assay

99%

form

liquid

refractive index

n20/D 1.452 (lit.)

bp

114 °C/75 mmHg (lit.)

density

1.337 g/mL at 25 °C (lit.)

SMILES string

CN(C)S(Cl)(=O)=O

InChI

1S/C2H6ClNO2S/c1-4(2)7(3,5)6/h1-2H3

InChI key

JFCHSQDLLFJHOA-UHFFFAOYSA-N

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Application

Applications of N,N -dimethylsulfamoyl chloride are:
  • It is widely used in the synthesis of a medicinally important class of compounds, sulfonamides.
  • It is used in the synthesis of aminotetralin derived sulfamides as anticancer agents and acetylcholinesterase inhibitors.
  • It can also be used in the esterification/amidation between carboxylic acids and equimolar amounts of alcohols/amines, as in the synthesis of coumaperine.

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Carc. 1B - Eye Dam. 1 - Skin Corr. 1B

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Acetylcholinesterase and carbonic anhydrase inhibitory properties of novel urea and sulfamide derivatives incorporating dopaminergic 2-aminotetralin scaffolds.
Ozgeris B, et al.
Bioorganic & Medicinal Chemistry, 24(10), 2318-2329 (2016)
Novel and efficient method for esterification, amidation between carboxylic acids and equimolar amounts of alcohols, and amines utilizing Me2NSO2Cl and N, N-dimethylamines; its application to the synthesis of coumaperine, a natural chemopreventive dieneamide.
Wakasugi K, et al.
Tetrahedron, 59(28), 5337-5345 (2003)
Catalytic arylation of sulfamoyl chlorides: A practical synthesis of sulfonamides.
Frost CG, et al.
Synlett, 2002(11), 1928-1930 (2002)
Synthesis and Anticancer Activity of Novel Ureas and Sulfamides Incorporating 1-Aminotetralins.
Ozgeris B, et al.
Archives of Medical Research (2017)

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