| Identification | More | [Name]
N,N-BIS(2-CHLOROETHYL)-P-TOLUENESULFONAMIDE | [CAS]
42137-88-2 | [Synonyms]
LABOTEST-BB LT00455209
N,N-BIS(2-CHLOROETHYL)-4-METHYLBENZENESULFONAMIDE
N,N-BIS(2-CHLOROETHYL)-P-TOLUENESULFONAMIDE
N,N-BIS(2-CHLOROETHYL)-P-TOLUENESULPHONAMIDE
N,N-BIS(B-CHLOROETHYL)-P-TOLUENESULFONAMIDE
N-N-BIS(BETA-CHLOROETHYL)-P-TOLUENESULFONAMIDE
Benzenesulfonamide, N,N-bis(2-chloroethyl)-4-methyl-
N,N-Bis(-chloroethyl)-p-toluenesulfonamide
N,N-Bis-(2-chloroethyl)-p-toluenesulfonamide, tech., 90% | [EINECS(EC#)]
255-677-7 | [Molecular Formula]
C11H15Cl2NO2S | [MDL Number]
MFCD00018944 | [Molecular Weight]
296.21 | [MOL File]
42137-88-2.mol |
| Chemical Properties | Back Directory | [Appearance]
GREY TO GREY-BROWN POWDER | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [HS Code ]
29350090 |
| Hazard Information | Back Directory | [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 |
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