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p-Toluenesulfonyl chloride is used as a precursor in the production of dyes and saccharin. It acts as a dehydrating agent in the conversion of urea to carbodiimide and converts alcohols into the corresponding toluenesulfonate esters. It is also employed as a flow-promoting agent for paints, an adhesive, nitrocellulose, coating material and as a plasticizer for polyamides. Furthermore, it serves as an antistatic agent, as a gloss enhancer in plastic film preparations and as a basic material of electroplating solutions.
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).
Cooley, T. A.; Riley, S.; Biros, S. M.; Staples, R. J.; Ngassa, F. N. Crystal structure of 2, 4-dinitrophenyl 4-methylbenzenesulfonate: a new polymorph. Nano lett. 2015, 71 (9), 1085-1088.
Jiang, X.; Yu, G. W.; Li, Z. G.; Chu, S. P.; Wang, S. P. Synthesis and characterisation of phosphazene derivatives containing dioxybiphenyl and 4-sulfanylquinazoline groups. J. Chem. Res., Synop. 2015, 39 (3), 162-165.
Hazard Statements: H290-H315-H317-H318
May be corrosive to metals. Causes skin irritation. May cause an allergic skin reaction. Causes serious eye damage.
Precautionary Statements: P234-P261-P264b-P272-P280-P302+P352-P305+P351+P338-P310-P333+P313-P362-P390-P501c
Keep only in original container. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. If skin irritation or rash occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. Absorb spillage to prevent material damage. Dispose of contents/ container to an approved waste disposal plant