| Identification | More | [Name]
alpha-Bromo-p-toluenesulphonyl chloride | [CAS]
66176-39-4 | [Synonyms]
4-(BROMOMETHYL)BENZENE-1-SULFONYL CHLORIDE
4-(BROMOMETHYL)BENZENESULFONYL CHLORIDE
4-(BROMOMETHYL)BENZENESULPHONYL CHLORIDE
4-(BROMOMETHYLENE)BENZENESULFONYL CHLORIDE
ALPHA-BROMO-P-TOLUENESULPHONYL CHLORIDE
BUTTPARK 94\04-08
alpha-Bromo-p-toluenesulfonylchloride
à-bromo-p-toluenesulfonyl chloride
α-bromo-p-toluenesulfonyl chloride
4-(Bromomethyl)benzenesulphonyl chloride 98%
4-(BROMOMETHYL)BENZENESULFONYL CHLORIDE 95% | [EINECS(EC#)]
627-352-3 | [Molecular Formula]
C7H6BrClO2S | [MDL Number]
MFCD00156129 | [Molecular Weight]
269.54 | [MOL File]
66176-39-4.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to light yellow crystalline powder | [Melting point ]
71-75 °C(lit.) | [Boiling point ]
160-170 °C | [density ]
1.6944 (estimate) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
Crystalline Powder | [color ]
Off-white to light yellow | [Sensitive ]
Moisture Sensitive | [BRN ]
2364328 | [CAS DataBase Reference]
66176-39-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [Hazard Note ]
Corrosive | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29049090 |
| Hazard Information | Back Directory | [Chemical Properties]
off-white to light yellow crystalline powder | [Uses]
4-(Bromomethyl)benzenesulfonyl chloride may be used to synthesize:
- 4-bromomethyl-N-(6-methoxy-quinolin-8-yl)-benzenesulfonamide
- benzene-sulfonamide derivatives, which are potent Chemokine Receptor Type 4 (CXCR4) inhibitors
- imidazole derivatives having antifungal activity
| [Synthesis]
General procedure for the synthesis of 4-bromomethylbenzenesulfonyl chloride from p-toluenesulfonyl chloride: to a stirred solution of p-toluenesulfonyl chloride (20 g, 104.9 mmol) in carbon tetrachloride (500 mL) was added sequentially N-bromosuccinimide (20.6 g, 115.7 mmol) and benzoyl peroxide (2.54 g, 10.84 mmol) at room temperature. The reaction mixture was refluxed for 10 hours and then filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure to give a yellow oil. The oily substance was recrystallized using hexane as eluent to give 4-bromomethylbenzenesulfonyl chloride (20.6 g, 65% yield) as a final white solid. | [References]
[1] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 5, p. 1487 - 1493
[2] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204
[3] Journal of the American Chemical Society, 1957, vol. 79, p. 4232
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 9, p. 2437 - 2451
[5] Patent: US5318980, 1994, A |
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