benzenesulfonyl chloride

• ChemBase ID: 77969
• Molecular Formular: C6H5ClO2S
• Molecular Mass: 176.6207
• Monoisotopic Mass: 175.96987808
• SMILES: S(=O)(=O)(c1ccccc1)Cl
• Canonical SMILES: ClS(=O)(=O)c1ccccc1
• InChI: InChI=1S/C6H5ClO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H
• InChIKey: CSKNSYBAZOQPLR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzenesulfonyl chloride
• IUPAC Traditional name: benzenesulfonyl chloride
• Synonyms: Benzenesulfonyl chloride; Benzenesulfochloride; Benzenesulfonyl Chloride; Benzenesulphonyl chloride 99%; 苯磺酰氯

Database IDs

• CAS Number: 98-09-9
• EC Number: 202-636-6
• MDL Number: MFCD00007426
• Beilstein Number: 606926
• Merck Index: 141072
• PubChem SID: 162042808; 24846801; 24846802
• PubChem CID: 7369

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.9195489
• LogD (pH = 7.4): 1.9195489
• Log P: 1.9195489
• Molar Refractivity: 40.2522 cm^3
• Polarizability: 16.404224 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 13-15 °C(lit.); 13-15°C; 14-15°C
• Boiling Point: 251-252 °C(lit.); 251-252°C; 252°C
• Flash Point: 132 °C; 132°C; 132°C(270°F); 269.6 °F
• Density: 1.377; 1.384; 1.384 g/mL at 25 °C(lit.)
• Refractive Index: 1.5525; n20/D 1.551; n20/D 1.551(lit.); n20/D 1.552
• Vapor Pressure: 0.04 mmHg ( 20 °C)

Safety Information

• Storage Warning: Corrosive/Lachrymatory/Moisture Sensitive/Store under Argon; Moisture Sensitive
• RTECS: DB8750000
• European Hazard Symbols: Corrosive (C); X
• UN Number: 2225; UN2225
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3; III
• Risk Statements: 20/22-34-42/43; 22-34
• Safety Statements: 23-26-36/37/39-45; 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H314-H317-H332-H334; H314-H318-H302
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P261-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2225 8/PG 3

Product Information

• Purity: ≥97.0% (AT); ≥99.0% (AT); 96%; 98%; 99%
• Grade: for HPLC derivatization; purum
• Cation Traces: Al: ≤0.5 mg/kg; Ba: ≤0.1 mg/kg; Bi: ≤0.1 mg/kg; Ca: ≤0.5 mg/kg; Cd: ≤0.05 mg/kg; Co: ≤0.02 mg/kg; Cr: ≤0.02 mg/kg; Cu: ≤0.02 mg/kg; Fe: ≤0.1 mg/kg; K: ≤0.5 mg/kg; Li: ≤0.1 mg/kg; Mg: ≤0.1 mg/kg; Mn: ≤0.02 mg/kg; Mo: ≤0.1 mg/kg; Na: ≤0.5 mg/kg; Ni: ≤0.02 mg/kg; Pb: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: ≤0.1 mg/kg
• Linear Formula: C6H5SO2Cl

DETAILS

Sigma Aldrich - 108138

Application
Useful reagent for preparing α-disulfones.1
Packaging
1 kg in glass bottle
5, 100, 500 g in glass bottle

Sigma Aldrich - 108111

Packaging
1, 3 kg in glass bottle
25 g in glass bottle

REFERENCES

• Reacts with ?-hydroxy esters in pyridine to give ?-lactones which, at higher temperatures eliminate CO₂ in a stereospecific alkene synthesis: J. Am. Chem. Soc., 94, 2000 (1972); J. Org. Chem., 39, 1322, 1650 (1974):
  
• Alternatively, MgBr₂ induces a ring-opening reaction leading to ?-unsaturated acids. See, e.g.: Synth. Commun., 19, 2243 (1989).