N,N-BIS(2-CHLOROETHYL)-P-TOLUENESULFONAMIDE Chemical Properties

Melting point:

43-50 °C

Boiling point:

409.1±55.0 °C(Predicted)

Density 

1.2228 (rough estimate)

refractive index 

1.6000 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Chloroform

form 

powder to crystal

pka

-8.48±0.70(Predicted)

color 

White to Light yellow

BRN 

2134258

InChIKey

PTVBBIMKLOMGSY-UHFFFAOYSA-N

CAS DataBase Reference

42137-88-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25

HS Code 

29350090

MSDS

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

N,N-BIS(2-CHLOROETHYL)-P-TOLUENESULFONAMIDE Usage And Synthesis

Chemical Properties

GREY TO GREY-BROWN POWDER

Uses

N,N-Bis(2-chloroethyl)-p-toluenesulfonaMide can be used as an intermediate used in the process for preparation of Cetirizine (C281100).

Synthesis

Bis(2-chloroethyl)amine hydrochloride (25.2 g, Tokyo Chemical Industry CO., LTD.) was suspended in dichloromethane (280 mL) and the suspension was cooled to 0 °C. Pyridine (24 mL) and p-toluenesulfonyl chloride (28.3 g) were added sequentially under stirring, followed by stirring the reaction mixture for 4 hours at room temperature. Upon completion of the reaction, saturated aqueous sodium bicarbonate solution was added to the mixture for neutralization, and then the organic phase was extracted with dichloromethane. The organic layer was washed sequentially with 1N aqueous hydrochloric acid and deionized water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product obtained was purified by silica gel column chromatography with the eluent being hexane-ethyl acetate in different ratios (15:1 to 5:1) to afford N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide (30.0 g, 71% yield). The structure of the product was confirmed by 1H-NMR (300 MHz, DMSO-d6): δ 2.41 (3H, s, CH3), 3.45 (4H, t, J = 6.9 Hz, CH2Cl), 3.72 (4H, t, J = 6.9 Hz, CH2N), 7.44 (2H, d, J = 8.2 Hz, ArH), 7.75 (2H, d, J = 8.2 Hz, ArH).

References

[1] Journal of Molecular Structure, 2009, vol. 923, # 1-3, p. 132 - 140
[2] Patent: EP1714961, 2006, A1. Location in patent: Page/Page column 18
[3] Patent: WO2013/175499, 2013, A2. Location in patent: Page/Page column 23
[4] Patent: US2014/179713, 2014, A1. Location in patent: Paragraph 0085
[5] RSC Advances, 2015, vol. 5, # 118, p. 97205 - 97211

N,N-BIS(2-CHLOROETHYL)-P-TOLUENESULFONAMIDE(42137-88-2)Related Product Information

• Bisbiphenyl-4-yl-(4'-broMo-biphenyl-4-yl)-aMine
• N,N-Dimethyl methanesulfonamide
• p-Toluenesulfonamide
• p-Toluenesulfonic acid
• Sulfamide
• N,N-DIMETHYL-P-TOLUENESULFONAMIDE
• Ethyl-p-toluenesulfonamide
• -EthylbenzenesulfonaMide
• N,N-Diethyl-4-methylbenzenesulfonamide
• N-Methyl-p-toluenesulfonamide
• N,N-BIS(2-CHLOROETHYL)-P-TOLUENESULFONAMIDE
• Nornitrogen mustard
• 4-[BIS-(2-CHLORO-ETHYL)-SULFAMOYL]-BENZOIC ACID
• N1,N1-DI(2-CHLOROALLYL)-4-METHYLBENZENE-1-SULFONAMIDE
• AKOS 360