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N,N-Dimethylsulfamide

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N,N-Dimethylsulfamide Basic information
Product Name:N,N-Dimethylsulfamide
Synonyms:dimethylsulfamide;N,N-DIMETHYLSULFAMIDE;N,N-DIMETHYLSULFAMOYLAMIDE;[methyl(sulfamoyl)amino]methane;EOS-60610;N.N-DiMethylsu;N,N-Dimethylsulfamide>;Sulfamide, N,N-dimethyl-
CAS:3984-14-3
MF:C2H8N2O2S
MW:124.16
EINECS:
Product Categories:Aliphatics;Amines;Sulfur & Selenium Compounds;API intermediates;CHIRAL CHEMICALS;sulfonyl compound
Mol File:3984-14-3.mol
N,N-Dimethylsulfamide Structure
N,N-Dimethylsulfamide Chemical Properties
Melting point 95-96
Boiling point 216.9±23.0 °C(Predicted)
density 1.327±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
pka11.41±0.60(Predicted)
form Solid
color White to Off-White
CAS DataBase Reference3984-14-3(CAS DataBase Reference)
EPA Substance Registry SystemSulfamide, N,N-dimethyl- (3984-14-3)
Safety Information
Safety Statements 24/25
HS Code 2935.90.9500
MSDS Information
N,N-Dimethylsulfamide Usage And Synthesis
Chemical PropertiesWhite Solid
UsesN,N-Dimethylsulfamide is a byproduct of Tolylfluanide (T536730) fungicide decomposition found in some waters. Upon ozonization it becomes a precursor for carcinogenic Nitrosodimethylamine (N525625). Otherwise N,N-Dimethylsulfamide is a versatile reactant used in various syntheses such as preparation of N-sulfonylbenzaldimines in copper-catalyzed aza-Friedel-Crafts reactions with 1-methylindole.
Synthesis
Dimethylsulfamoyl chloride

13360-57-1

N,N-Dimethylsulfamide

3984-14-3

General procedure for the synthesis of N,N-dimethylsulfonamide from N,N-dimethylaminosulfonyl chloride: N,N-dimethylaminosulfonyl chloride (6.96 mmol, 0.748 mL) was reacted with a methanol solution of 7 N ammonia (104 mmol, 14.92 mL) in a sealed autoclave at 60°C for 16 hours. After completion of the reaction, the solvent was removed from the reaction mixture by evaporation. The resulting solid was suspended in dichloromethane (DCM), filtered and washed with DCM. Subsequently, it was dried under reduced pressure to afford N,N-dimethylsulfonamide (850 mg, yield: 98%), which could be used in subsequent steps without further purification. The product was characterized by 1H NMR (300 MHz, DMSO-d6) with chemical shifts of δ 7.40 (2H, s), 2.38 (6H, s).

References[1] Patent: WO2013/149997, 2013, A1. Location in patent: Page/Page column 146; 147
[2] Patent: WO2013/102826, 2013, A1. Location in patent: Page/Page column 84
[3] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1980, vol. 19, # 10, p. 935 - 937
[4] Tetrahedron Letters, 2009, vol. 50, # 19, p. 2232 - 2235
[5] Chemische Berichte, 1950, vol. 83, p. 551,554
N,N-Dimethylsulfamide Preparation Products And Raw materials
Raw materialsDimethylsulfamoyl chloride-->Methanol-->Ammonia
Tag:N,N-Dimethylsulfamide(3984-14-3) Related Product Information
Cyclopropanesulfonamide Benzenesulfonamide TRIFLUOROMETHANESULFONYL FLUORIDE Dimethyl sulfone Ethanesulfonamide Methanesulfonamide 3-Aminobenzenesulfonamide Poly(dimethylsiloxane) p-Toluenesulfonamide N,N-Dimethylbenzylsulfamide Sulfanilamide N,N-Dimethylformamide Burgess reagent DICHLOFLUANID Bentazone N,N,N',N'-TETRAETHYLSULFAMIDE 2-(N,N-Dimethylsulphamoyl)phenylboronic acid N,N,N',N'-TETRAMETHYLSULFONAMIDE