N,N-Dimethylsulfamide

N,N-Dimethylsulfamide Property

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)

form 

Solid

pka

11.41±0.60(Predicted)

color 

White to Off-White

CAS DataBase Reference

3984-14-3(CAS DataBase Reference)

EPA Substance Registry System

Sulfamide, N,N-dimethyl- (3984-14-3)

Safety

Safety Statements 

24/25

HS Code 

2935.90.9500

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

N,N-Dimethylsulfamide Chemical Properties,Usage,Production

Chemical Properties

White Solid

Uses

N,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

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