4-methylbenzene-1-sulfonyl chloride

• ChemBase ID: 70354
• Molecular Formular: C7H7ClO2S
• Molecular Mass: 190.64728
• Monoisotopic Mass: 189.98552814
• SMILES: c1(ccc(cc1)C)S(=O)(=O)Cl
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)Cl
• InChI: InChI=1S/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3
• InChIKey: YYROPELSRYBVMQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methylbenzene-1-sulfonyl chloride
• IUPAC Traditional name: P-toluenesulfonyl chloride
• Synonyms: p-toluenesulfonyl chloride; p-TsCe; TsCl; 4-Toluenesulfonyl chloride; 4-Methylbenzenesulfonyl chloride; Tosyl chloride; p-TOLUENESULFONYL CHLORIDE; p-Toluenesulfonyl chloride; 4-Methylbenzenesulphonyl chloride; 4-Methylbenzene-1-sulfonyl chloride; 4-Methylbenzenesulfonyl chloride; 4-甲苯磺酰氯; 对甲苯磺酰氯

Database IDs

• CAS Number: 98-59-9
• EC Number: 202-684-8
• MDL Number: MFCD00007450
• Beilstein Number: 607898
• Merck Index: 149534
• PubChem SID: 24889256; 24889257; 24900152; 162036074; 24854440
• PubChem CID: 7397
• Chemspider ID: 7119
• Wikipedia Title: 4-Toluenesulfonyl_chloride

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.4329703
• LogD (pH = 7.4): 2.4329703
• Log P: 2.4329703
• Molar Refractivity: 45.2934 cm^3
• Polarizability: 18.15714 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: hydrolysis in water; methylene chloride: soluble0.2 g/mL, clear; Soluble in alcohol, benzene, and ether. Insoluble in water
• Apperance: White solid
• Melting Point: 65-69 °C; 65-69 °C(lit.); 66-69 °C; 67.4 °C; 67.4°C; 67-70°C; 67-70°C
• Boiling Point: 134 °C at 10 mmHg; 134 °C/10 mmHg(lit.); 134.5 °C at 10 mmHg; 151.6 °C at 20 mmHg; 146°C/15mm; 146°C/15mm
• Flash Point: 128 °C (closed cup); 128 °C; 128°C; 128°C(262°F); 262.4 °F
• Density: 1.33 g/ml; 1.35
• Vapor Pressure: 1 mmHg ( 88 °C); 1 mmHg at 88 °C

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate, Store Under Nitrogen
• Storage Warning: Corrosive/Moisture Sensitive/Store under Argon; IRRITANT; Moisture Sensitive
• RTECS: DB8929000
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: 1759; 3261; UN3261
• German water hazard class: 1
• Hazard Class: 8
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 34; 38-41; R:34
• Safety Statements: 26-36/37/39-45-60; 26-39; S:26-27/28-36/37/39-46-64
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: false; 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• Main Hazard: releases acid
• NFPA704:
  

  1

  3

  0
• GHS Hazard statements: H314-H318; H315-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: ≥97.0% (AT); ≥98%; ≥99%; ≥99.0% (AT); 95+%; 98%
• Grade: puriss.; purum; reagent grade; ReagentPlus®
• Linear Formula: CH3C6H4SO2Cl

DETAILS

MP Biomedicals - 05218665

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02152653

Crystalline

Sigma Aldrich - T35955

Packaging
1 kg in poly bottle
1 kg packaged in glass bottles; 3 kg packaged in open-head poly drums
3 kg in poly drum

Sigma Aldrich - 240877

Packaging
100 g in poly bottle
5 g in glass bottle
500 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• For a detailed study of the optimum conditions for the tosylation of primary and secondary alcohols in pyridine, see: J. Org. Chem., 51, 2386 (1986). For use of 1,4-Diazabicyclo[2.2.2]octane, A14003, as an alternative to pyridine in the tosylation of alcohols, see: Synthesis, 1433 (1997). In the presence of a carboxylic acid, the ester is formed in high yield: J. Am. Chem. Soc., 77, 6214 (1955); 79, 2146 (1957). Esterification of an unprotected amino acid can be effected by heating the tosylate salt with tosyl chloride in an alcohol solvent: J. Org. Chem., 48, 121 (1983).
• In the presence of strong bases, 1,2-diols can be converted to epoxides: Synthesis, 706 (1977); 983 (1985); Synth. Commun., 23, 285 (1993), and 1,3-diols to oxetanes: Synthesis, 550 (1981).
• N-Tosylation has been used to block the imidazole nucleus in histidine: Bull. Chem. Soc. Jpn., 42, 1466 (1969); 47, 3146 (1974), and arginine residues: Experientia, 24, 661 (1968), during peptide synthesis. Cleavage can be effected with HF. See Appendix 6.
• Dehydrating agent, e.g. for conversion of ureas to carbodiimides: Org. Synth. Coll., 5, 555 (1973); Synthesis, 520 (1987).