2-PHENYL-ETHANESULFONYL CHLORIDE Chemical Properties

Melting point:

32-33 °C

Boiling point:

121-123 °C(Press: 3 Torr)

Density 

1.323±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

Appearance

White to light yellow <32°C Solid,>33°C Liquid

InChI

InChI=1S/C8H9ClO2S/c9-12(10,11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2

InChIKey

LKFNLHZZPHHFEC-UHFFFAOYSA-N

SMILES

C1(CCS(Cl)(=O)=O)=CC=CC=C1

Safety Information

RIDADR 

1759

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

2-PHENYL-ETHANESULFONYL CHLORIDE Usage And Synthesis

Synthesis

Example 15 Synthesis of 2-phenylethanesulfonyl chloride: N-chlorosuccinimide (534 mg, 4.00 mmol) was dissolved in a 2M HCl-CH3CN mixed solvent (267.4 μL - 1.34 mL, 3v/w volume relative to N-chlorosuccinimide). To this solution, a CH3CN solution (267.4 μL, 0.5 v/w relative to the volume of N-chlorosuccinimide) of 2-phenylethanethiol (134 μL, 1.00 mmol) was slowly added at 10 °C. After 30 min of reaction, ether was added to the reaction mixture, followed by three extractions with brine. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 2-phenylethanesulfonyl chloride (195.5 mg, 95.4% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.43-7.27 (m, 5H), 3.98-3.92 (m, 3H), 3.41-3.35 (m, 1H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 8, p. 1181 - 1184
[2] Patent: US2015/329533, 2015, A1. Location in patent: Paragraph 0147; 0148
[3] Advanced Synthesis and Catalysis, 2015, vol. 357, # 18, p. 3825 - 3830
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3183 - 3203
[5] Journal of the American Chemical Society, 1991, vol. 113, # 6, p. 2259 - 2263

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