4-tert-Butylbenzenesulfonamide Chemical Properties

Melting point:

136-138°C

Boiling point:

337.2±35.0 °C(Predicted)

Density 

1.152±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Sparingly)

form 

Solid

pka

10.22±0.10(Predicted)

color 

White to Off-White

InChIKey

KYDZEZNYRFJCSA-UHFFFAOYSA-N

CAS DataBase Reference

6292-59-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22

Safety Statements 

22-36/37/39

Hazard Note 

Irritant

HS Code 

29350090

4-tert-Butylbenzenesulfonamide Usage And Synthesis

Chemical Properties

White solid

Uses

4-tert-Butylbenzenesulfonamide is an intermediate as well as a degradation impurity of the endothelin receptor antagonist Bosentan (B675900).

Synthesis

A solution of 4-(tert-butyl)benzenesulfonyl chloride (2.30 g, 10.0 mmol) in dichloromethane (100 mL) was added to a 500 mL round bottom flask at 0 °C, followed by the slow addition of concentrated ammonia (50 mL, 100 mmol, 10 equiv). The reaction mixture was gradually warmed to room temperature and stirred continuously for 20 hours. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure and the resulting slurry was filtered through a Brinell funnel to afford 1.60 g (75% yield) of 4-(tert-butyl)benzenesulfonamide (Compound A) as a white solid.

References

[1] Chemische Berichte, 1993, vol. 126, # 7, p. 1713 - 1722
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 21, p. 3355 - 3368
[3] Patent: US2004/39033, 2004, A1. Location in patent: Page/Page column 16; 64
[4] European Journal of Medicinal Chemistry, 2004, vol. 39, # 10, p. 835 - 847
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 16, p. 4397 - 4406

4-tert-Butylbenzenesulfonamide(6292-59-7)Related Product Information

• N-n-Butyl benzene sulfonamide
• 4-tert-Butylbenzoyl chloride
• Methyl 4-tert-butylbenzoate
• tert-Butyl methyl ether
• Benzenesulfonamide
• Sulfanilamide
• 3-Aminobenzenesulfonamide
• 4-tert-Butylphenol
• tert-Butanol
• 4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide
• 4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine
• BenzenesulfonaMide, N,N'-[1,2-ethanediylbis[oxy[5-(2-Methoxyphenoxy)[2,2'-bipyriMidine]-6,4-diyl]]]bis[4-(1,1-diMethylethyl)-
• BenzenesulfonaMide, N-[1,6-dihydro-5-(2-Methoxyphenoxy)-6-oxo[2,2'-bipyriMidin]-4-yl]-4-(1,1-diMethylethyl)-
• Bosentan Related Compound 4
• Bosentan Related Compound 5
• Bosentan Impurity 15 HCl
• 2-Bromo-N-tert-butylbenzenesulfonamide
• Recombinant Human Telomerase