3-PHENYLBENZENESULFONYL CHLORIDE

3-PHENYLBENZENESULFONYL CHLORIDE Property

Melting point:

38-40 °C

Boiling point:

397.8±21.0 °C(Predicted)

Density 

1.320±0.06 g/cm3(Predicted)

storage temp. 

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

form 

viscous liquid

color 

Clear, yellow

Safety

Hazard Codes 

C,Xi

Risk Statements 

36

Safety Statements 

26

RIDADR 

UN3261

Hazard Note 

Corrosive

HazardClass 

8

HS Code 

2904990090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

3-PHENYLBENZENESULFONYL CHLORIDE Chemical Properties,Usage,Production

Synthesis

[1,1'-Biphenyl]-3-yl(benzyl)thiolane (450 mg, 1.63 mmol) was used as a raw material to synthesize [1,1'-biphenyl]-3-sulfonyl chloride according to General Method J. The synthesis was carried out by using a mixture of acetic acid/water (3:1, v/v; 0.1 mmol/mL) and N-chlorobutanediyl chloride (3:1, v/v; 0.1 mmol/mL). The procedure was as follows: the raw material was dissolved in a mixed solvent of acetic acid/water (3:1, v/v; 0.1 mmol/mL) at room temperature, and N-chlorosuccinimide (NCS, 6 equiv) was added. The reaction mixture was stirred at the same temperature for 3-6 h. The reaction progress was monitored by HPLC. After completion of the reaction, the solvent was removed by concentration under reduced pressure, saturated aqueous sodium bicarbonate was added and extracted with ethyl acetate (EtOAc). The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the crude product was concentrated under reduced pressure and purified by Combifiash silica gel column chromatography (100% hexane as eluent) to afford [1,1'-biphenyl]-3-sulfonyl chloride 250 mg (5.9% yield) as a colorless solid. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.28-8.24 (m, 1H), 8.05-8.01 (m, 1H), 7.98-7.95 (m, 1H), 7.74-7.68 (m, 1H), 7.66-7.61 (m, 2H), 7.56-7.49 (m, 2H), 7.49- 7.43 (m, 1H).

References

[1] ChemMedChem, 2016, vol. 11, # 23, p. 2607 - 2620
[2] Patent: WO2018/52903, 2018, A1. Location in patent: Page/Page column 22-23; 58