2-Nitrobenzenesulfonamide Chemical Properties

Melting point:

190-192 °C (lit.)

Boiling point:

418.8±47.0 °C(Predicted)

Density 

1.505 (estimate)

refractive index 

1.6490 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO, Methanol (Slightly, Heated, Sonicated)

form 

solid

pka

9.24±0.60(Predicted)

color 

Off-White to Brown

Water Solubility 

Slightly soluble in water.

BRN 

2214215

InChI

InChI=1S/C6H6N2O4S/c7-13(11,12)6-4-2-1-3-5(6)8(9)10/h1-4H,(H2,7,11,12)

InChIKey

GNDKYAWHEKZHPJ-UHFFFAOYSA-N

SMILES

C1(S(N)(=O)=O)=CC=CC=C1[N+]([O-])=O

CAS DataBase Reference

5455-59-4(CAS DataBase Reference)

NIST Chemistry Reference

2-Nitrobenzenesulfonamide(5455-59-4)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-20/21/22

Safety Statements 

36/37/39-26-22-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29350090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Nitrobenzenesulfonamide Usage And Synthesis

Chemical Properties

yellow to light brown crystalline powder

Uses

2-Nitro-benzenesulfonamide is a carbonic anhydrase inhibitor.

Synthesis

The general procedure for the synthesis of 2-nitrobenzenesulfonamide from o-nitrobenzenesulfonyl chloride was as follows: 120.0 g of 2-nitrobenzenesulfonyl chloride (Compound 1, 0.78 mol) was dissolved in 280 mL of tetrahydrofuran (THF) with 360.0 g of ammonium acetate (4.7 mol), heated to reflux and stirred overnight. After completion of the reaction, the solid product was collected by filtration and processed by vacuum drying to afford 86.0 g of 2-nitrobenzenesulfonamide (compound 2) as a yellow solid in 80% yield.

References

[1] Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 9088 - 9095
[2] Patent: CN104761514, 2016, B. Location in patent: Paragraph 0023-0025
[3] Patent: JP2005/314398, 2005, A. Location in patent: Page/Page column 25
[4] Justus Liebigs Annalen der Chemie, 1875, vol. 177, p. 62
[5] Magnetic Resonance in Chemistry, 1987, vol. 25, p. 189 - 193

2-Nitrobenzenesulfonamide(5455-59-4)Related Product Information

• Benzenesulfonamide
• 2-Nitrobenzenesulfenyl chloride
• Sulfamide
• 4-Nitrobenzoic acid
• Sodium 3-nitrobenzenesulphonate
• 1,3-Dinitrobenzene
• Sulfanilamide
• Nitrobenzene
• 2-Nitrochlorobenzene
• 2-NITROPHENOL-4-SULFOMETHYL AMIDE
• N-CYCLOHEXYL 3-NITROBENZENESULFONAMIDE
• N-BUTYL 3-NITROBENZENESULFONAMIDE
• N-Cyclopropyl 4-Nitrophenylsulfonamide
• N-METHYL 3-NITROBENZENESULFONAMIDE
• 4-CHLORO-N,N-DIETHYL-3-NITROBENZENESULFONAMIDE
• N-T-BUTYL 3-NITROBENZENESULFONAMIDE
• N-ISOPROPYL 3-NITROBENZENESULFONAMIDE
• 4-Nitrobenzenesulfonamide