(4-Nitrophenyl)methanesulfonyl chloride Chemical Properties

Melting point:

91-92°C

Boiling point:

396.4±25.0 °C(Predicted)

Density 

1.570±0.06 g/cm3(Predicted)

storage temp. 

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

Appearance

Yellow to brown Solid

Water Solubility 

Reacts with water.

Sensitive 

Moisture Sensitive

CAS DataBase Reference

4025-75-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xn

Risk Statements 

14-29-34-22

Safety Statements 

22-26-30-36/37/39-45

RIDADR 

UN3261

HazardClass 

8

PackingGroup 

II

HS Code 

2904990090

(4-Nitrophenyl)methanesulfonyl chloride Usage And Synthesis

Uses

4-Nitrobenzylsulfonyl Chloride is used for preparation of HIV-1 Tat protein via native chemical ligation between a peptide thioester and a peptide containing (mercapto)leucine at N-terminus followed by desulfurization.

Synthesis

The general procedure for the synthesis of (4-nitrophenyl)methanesulfonyl chloride from 4-nitrophenylaminosulfate methyl ester hydrochloride is as follows: 1. the alkyl halide (or sulfate) (5 mmol) was heated with thiourea (0.381 g, 5 mmol) in ethanol (5 mL) at reflux for 1 hour. 2. Upon completion of the reaction, the solvent was removed under vacuum and the residue was washed with ether (3 x 5 mL) to afford the corresponding S-alkyl isothiourea salt as a white solid in near quantitative yield. 3. Without further purification, the resulting S-alkylisothiourea salt was transferred to a three-necked round-bottomed flask equipped with a thermometer and a charging funnel and placed in an ice bath. 4. Water (0.45 mL) and acetonitrile (10 mL) were added to the flask to form a vigorously stirred mixture. 5. A solution of tert-butyl hypochlorite (t-BuOCl, 2.86 mL) in acetonitrile (5 mL) was added slowly and dropwise while maintaining an internal temperature of 0-20°C. The solution was then mixed with water (0.45 mL) and acetonitrile (10 mL). 6. After the dropwise addition was completed, the reaction mixture was continued to be stirred for 30 minutes. 7. Upon completion of the reaction, the solvent was removed under vacuum and ether (15 mL) was added to dissolve the residue. 8. The ether layer was washed with water (2 x 10 mL) and dried with anhydrous sodium sulfate (Na2SO4). 9. 9. After drying, the ether solution is concentrated in vacuum to give high purity (4-nitrophenyl)methanesulfonyl chloride. 10. The product can be further purified by recrystallization from a mixed petroleum ether-ethyl acetate solvent.

References

[1] Synthesis (Germany), 2015, vol. 47, # 20, p. 3186 - 3190
[2] Synlett, 2013, vol. 24, # 16, p. 2165 - 2169
[3] Synthesis (Germany), 2014, vol. 46, # 2, p. 225 - 229

(4-Nitrophenyl)methanesulfonyl chloride(4025-75-6)Related Product Information

• Benzyl chloride
• Oxalyl chloride
• Sulfuryl chloride
• Tosyl chloride
• Ammonium chloride
• Choline chloride
• 1-Chloro-3-nitrobenzene
• Benzenesulfonyl chloride
• Zinc chloride
• Thionyl chloride
• Sodium chloride
• Calcium chloride
• 4-Nitrobenzenesulfonyl chloride
• 2-Nitrobenzenesulfenyl chloride
• Potassium chloride
• Sumatriptan-d6
• GR 49336
• SUMATRIPTAN-D6 SUCCINATE