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

Major Application

pharmaceutical (small molecule)

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