N-(3-Aminophenyl)methanesulfamide

N-(3-Aminophenyl)methanesulfamide Property

Melting point:

117-121 °C (lit.)

Boiling point:

361.8±44.0 °C(Predicted)

Density 

1.408±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

9.12±0.10(Predicted)

InChI

InChI=1S/C7H10N2O2S/c1-12(10,11)9-7-4-2-3-6(8)5-7/h2-5,9H,8H2,1H3

InChIKey

UQRRCQRFQGOHAI-UHFFFAOYSA-N

SMILES

CS(NC1=CC=CC(N)=C1)(=O)=O

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29350090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

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.

N-(3-Aminophenyl)methanesulfamide Chemical Properties,Usage,Production

Chemical Properties

Light red solid

Uses

Reactant for:

• Preparation of biologically and pharmacologically active molecules

Synthesis

The general procedure for the synthesis of m-aminomethanesulfonanilide from N-(methylsulfonyl)-3-nitroanilide was as follows: N-(3-nitrophenyl)methanesulfonamide (2.6 g, 12.0 mmol, 1.00 equiv), iron powder (3.38 g, 60.5 mmol, 5.03 equiv) and ammonium chloride (6.48 g, 121 mmol, 10.1 equiv) were dissolved in a solvent mixture of methanol (40 mL) and water (20 mL). The reaction mixture was heated at 70 °C for the reaction. After completion of the reaction, the insoluble material was removed by filtration through diatomaceous earth. The filtrate was concentrated under reduced pressure, diluted with ethyl acetate, washed twice sequentially with saturated saline and the organic phase was dried with anhydrous sodium sulfate. Finally, it was purified by column chromatography (silica gel 115 g, eluent: 20% to 40% ethyl acetate/hexane) to give 1.55 g of orange solid product in 69% yield.

References

[1] Patent: WO2014/6066, 2014, A1. Location in patent: Paragraph 0235
[2] Patent: WO2012/59932, 2012, A1. Location in patent: Page/Page column 149-150
[3] ChemMedChem, 2014, vol. 9, # 5, p. 962 - 972
[4] Patent: US2663732, 1950,