4-Hydrazinobenzene-1-sulfonamide hydrochloride Chemical Properties

Melting point:

149-152 °C(lit.)

Density 

1.644[at 20℃]

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Methanol (Slightly, Heated), Water (Slightly)

form 

powder to crystal

color 

White to Light yellow to Light orange

Water Solubility 

Soluble in water.

Sensitive 

Hygroscopic

InChI

InChI=1S/C6H9N3O2S.ClH/c7-9-5-1-3-6(4-2-5)12(8,10)11;/h1-4,9H,7H2,(H2,8,10,11);1H

InChIKey

IKEURONJLPUALY-UHFFFAOYSA-N

SMILES

C1(S(=O)(=O)N)C=CC(NN)=CC=1.Cl

LogP

-0.99 at 20℃

CAS DataBase Reference

17852-52-7(CAS DataBase Reference)

EPA Substance Registry System

Benzenesulfonamide, 4-hydrazinyl-, hydrochloride (1:1) (17852-52-7)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

36-24/25

WGK Germany 

3

RTECS 

DA9380000

Hazard Note 

Irritant

HS Code 

29350090

MSDS

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

4-Hydrazinobenzene-1-sulfonamide hydrochloride Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

Intermediate in the production of Celebrex.

Uses

It is a potentially useful intermediate in the production of Celebrex an anti inflammatory drug.

Flammability and Explosibility

Non flammable

Synthesis

The general procedure for the synthesis of p-hydrazinylbenzenesulfonamide hydrochloride from crystalline sulfanilamide was as follows: firstly, 4'-methylacetophenone was reacted with succinic anhydride in the presence of diisopropanolamine (LDA) and tetrahydrofuran (THF) for 1 hr at -78 °C to afford p-tolyl-4,6-dioxohexanoic acid in 66% yield and the product was a white solid. Subsequently, the sulfonamide was reacted with sodium nitrite (NaNO2) and concentrated hydrochloric acid for 30 min at 0-4 °C, followed by the addition of tin(II) chloride (SnCl2), and the reaction was continued for 4 h at 0 °C to produce 4-sulfonylaminophenylhydrazine hydrochloride in 55% yield, the product being a pale yellow solid. Finally, p-tolyl-4,6-dioxohexanoic acid was reacted with 4-sulfonylaminophenylhydrazine hydrochloride in a methanolic solution of triethanolamine (TEA) at room temperature for 16 h to give compound 30c, 3-[1-{p-(p-(sulfonylamino)phenyl}-5-p-tolyl-1H-pyrazol-3-yl]propanoic acid in 76% yield and the product was a yellow solid.

References

[1] Journal of Medicinal Chemistry, 2007, vol. 50, # 18, p. 4444 - 4452
[2] Organic Letters, 2012, vol. 14, # 19, p. 5030 - 5033,4
[3] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 4, p. 913 - 922
[4] Patent: US2007/292352, 2007, A1. Location in patent: Page/Page column 45-46
[5] Patent: US2003/236294, 2003, A1. Location in patent: Page 9

4-Hydrazinobenzene-1-sulfonamide hydrochloride(17852-52-7)Related Product Information

• Hydrazine monohydrochloride
• Sulfanilamide
• Benzenesulfonamide
• Benzoyl hydrazine
• Topotecan hydrochloride
• 4-Methylbenzenesulfonhydrazide
• 1,5-Diphenylcarbazide
• Phenylhydrazine hydrochloride
• 4-AMINOAZOBENZENE HYDROCHLORIDE
• D-Glucosamine hydrochloride
• Celecoxib Trifluro Impurity
• 5-(TRIFLUOROMETHYL)-3-P-TOLYL-1H-PYRAZOLE
• 4-[5-hydroxy-3-(4-methylphenyl)-5-(trifluoromethyl)-4H-pyrazol-1-yl]benzenesulfonamide
• Celecoxib Impurity 6
• Celecoxib iMpurity-G
• Celecoxib IMpurity 1
• Celecoxib Impurity 2
• Celecoxib Impurity