p-Toluenesulfonyl chloride

• Catalog No.: A14547
• CAS Number: 98-59-9
• M. F.: C7H7ClO2S
• M. W.: 190.64728
• Purity: 98%

SYNONYMS

• Title: 对甲苯磺酰氯
• IUPAC name: 4-methylbenzene-1-sulfonyl chloride
• IUPAC Traditional name: P-toluenesulfonyl chloride
• Synonyms: 4-Methylbenzenesulfonyl chloride; Tosyl chloride

DATABASE IDS

• MDL Number: MFCD00007450
• Merck Index: 149534
• Beilstein Number: 607898
• EC Number: 202-684-8
• CAS Number: 98-59-9

PROPERTIES

• Density: 1.35
• Flash Point: 128°C(262°F)
• Melting Point: 67-70°C
• Solubility: Soluble in alcohol, benzene, and ether. Insoluble in water
• Boiling Point: 146°C/15mm
• GHS Hazard statements: H314-H318
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
• Risk Statements: 34
• RTECS: DB8929000
• Safety Statements: 26-36/37/39-45-60
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN3261
• Packing Group: II
• Purity: 98%

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).