CHEMICAL NAME: P-Toluene Sulfony Chloride (PTSC)
CHEMICAL FORMULA: C7H7ClO2S
PROPERTY: P-Toluene Sulfony Chloride White crystalline
USE: Intermediates in the synthesis of drugs, dyestuff and auxiliaries.
PACKING: 25kg plastic woven bag, or 50kg fiber drum.
|Free acid ≤||0.1%|
|o-Toluene Sulfonyl Chloride ≤||0.1%|
(sulfonyl transfer reagent; O-sulfonylation of alcohols for conversion to chlorides or intermolecular and intramolecular displacements, vicinal diols for epoxidation, 1,3-diols for oxetane formation, carboxylic acids for esterification or decarboxylation, oximes for Beckmann rearrangements or fragmentations and Neber rearrangements, hydroxamic acids for Lossen rearrangements, nitrones for rearrangements, conversion of N-cyclopropylhydroxylamines to β-lactams; N-sulfonylation of aliphatic amines for subsequent deamination or displacement, aromatic amines for protection; C-sulfonylation of alkenes and silylalkynes; dehydration of ureas, formamides, and amides)
Alternate Names: tosyl chloride.
Physical Data: mp 67–69 °C; bp 146 °C/15 mmHg.
Solubility: insol H2O; freely sol ethanol, benzene, chloroform, ether.
Form Supplied in: white solid, widely available.
Purification: upon prolonged standing the material develops impurities of p-toluenesulfonic acid and HCl. Tosyl chloride is purified by dissolving 10 g in a minimum volume of CHCl3 (ca. 25 mL), filtering, and diluting with five volumes (ca. 125 mL) of petroleum ether (bp 30–60 °C) to precipitate impurities (mostly tosic acid, mp 101–104 °C). The solution is filtered, clarified with charcoal, and concentrated to ca. 40 mL by evaporation. Further evaporation to a very small volume gives 7 g of pure white crystals (mp 67.5–68.5 °C).
Tosyl chloride may also be recrystallized from petroleum ether, from benzene, or from toluene/petroleum ether (bp 40–60 °C) in the cold. Tosyl chloride in diethyl ether can be washed with aqueous 10% NaOH until colorless, then dried with Na2SO4 and crystallized by cooling in powdered dry ice. It can also be purified by dissolving in benzene, washing with aqueous 5% NaOH, drying with K2CO3 or MgSO4, and distilling under reduced pressure.
Handling, Storage, and Precautions: freshly purified tosyl chloride should be used for best results. Tosyl chloride is a moisture-sensitive, corrosive lachrymator.
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