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Tosyl chloride
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Tosyl chloride
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Tosyl chloride CAS NO.98-59-9
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Tosyl chloride ( p-Toluenesulfonyl Chloride ) -- CHemwill
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98-59-9 Usage

Contact allergens

Tosyl chloride is used mainly in the preparation of chemical derivatives in the pharmaceutical, plastics, and organic chemical industries.

Production method

Toluene chlorosulfonation production into o-toluenesulfonyl chloride, at the same time p-toluenesulfonyl chloride is also generated. The filter cake was separated from the o-toluenesulfonyl chloride, refined to obtain p-toluenesulfonyl chloride.

Chemical Properties

White to yellow solid

Uses

It can be used for organic synthesis, for example: dyes, saccharin,etc.

General Description

A white to gray powdered solid with a distinctive odor. Insoluble in water and denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation and skin absorption. Used to make other chemicals.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Chemical Properties

White flaky crystal. melting point is 71 ℃. Boiling point is 151.6 ℃ (1.67kPa), 145-146 ℃ (2.0kPa). Soluble in alcohol, ether and benzene, insoluble in water.

Purification Methods

Material that has been standing for a long time contains tosic acid and HCl and has m ca 65-68o. It is purified by dissolving (10g) in the minimum volume of CHCl3 (ca 25mL) filtered, and diluted with five volumes (i.e. 125mL) of pet ether (b 30-60o) to precipitate impurities. The solution is filtered, clarified with charcoal and concentrated to 40mL by evaporation. Further evaporation to a very small volume gives 7g of white crystals which are analytically pure, m 67.5-68.5o. (The insoluble material is largely tosic acid and has m 101-104o.) [Pelletier Chem Ind (London) 1034 1953.] It also crystallises from toluene/pet ether in the cold, from pet ether (b 40-60o) or *benzene. Its solution in diethyl ether has been washed with aqueous 10% NaOH until colourless, then dried (Na2SO4) and crystallised by cooling in powdered Dry-ice. It has also been purified by dissolving in *benzene, washing with aqueous 5% NaOH , then dried with K2CO3 or MgSO4, and distilled under reduced pressure and can be sublimed at high vacuum [Ebel Chem Ber 60 20861927]. [Beilstein 11 IV 375.]

Air & Water Reactions

Insoluble in water.

Tosyl chloride

Toluenesulfonyl chloride is an important intermediate dyes in organic synthesis and raw materials for pesticides, there are three kinds of isomers, namely o-toluenesulfonyl chloride, m-toluenesulfonyl chloride and p-toluenesulfonyl chloride. Relative molecular mass is 190.65. All three stimulate skin and mucous membranes, commonly used is adjacent toluenesulfonyl chloride and p-toluenesulfonyl chloride.
O-toluenesulfonyl chloride, also known as 2-methyl-benzenesulfonyl chloride, 2-toluene-sulfonyl chloride, is colorless oily liquid. The relative density is 1.3383. Melting point is 10.2 ℃. Boiling point is 154 ℃ (4.800 × 103Pa), 126 ℃ (1.333 × 103Pa). The refractive index is 1.5565. It is insoluble in water, soluble in ether, benzene and ethanol.
M-toluenesulfonyl chloride, also known as 3-methyl-benzenesulfonyl chloride, 3-toluenesulfonyl chloride, is colorless oily liquid. Melting point is 11.7 ℃. Boiling point is 146 ℃ (2.933 × 103Pa). It is insoluble in water, soluble in alcohol, ether and benzene.
P-toluenesulfonyl chloride is also known as 4-methyl-benzenesulfonyl chloride, 4-toluenesulfonyl chloride. Precipitation from ether or petroleum ether is triclinic white flaky crystal. The relative density is 1.26. Melting point is 11. 7 ℃. Boiling point is 164 ℃ (4.4 × 103Pa), 151.6 ℃ (2.666 × 103Pa), 145~146 ℃ (2.000 × 103Pa), 134.5 ℃ (1.333 × 103Pa). It is insoluble in water, soluble in alcohol, benzene and ether.
Toluenesulfonyl chloride is called "TsCl", with strong nucleophilicity and substitution reaction with nucleophilic reagent. For example, reaction with the alcohol into the ester:
ROH + TsCl-Py → ROTs + Py + HCl-, reaction with amine and hydrazine respectively to generate the sulfonamide and sulfonyl hydrazide:

The above information were edited and collated by Xiaonan of Chemicalbook.

Usage

1. The goods is an intermediate for disperse dyes, azoic dyes, acid dyes. Also used in the production of drugs homosulfanilamide.
2. Used for the analysis Reagents, but also for organic synthesis, dye preparation and molecule rearrangement in the hormone synthesis.
3. Used for organic synthesis, sulfa drugs and as pesticide intermediates.
InChI:InChI=1/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3

98-59-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma-Aldrich (T35955)  p-Toluenesulfonylchloride  reagent grade, ≥98% 98-59-9 T35955-3KG 1,959.75CNY Detail
Sigma-Aldrich (T35955)  p-Toluenesulfonylchloride  reagent grade, ≥98% 98-59-9 T35955-1KG 932.49CNY Detail
Sigma-Aldrich (T35955)  p-Toluenesulfonylchloride  reagent grade, ≥98% 98-59-9 T35955-250G 375.57CNY Detail
Sigma-Aldrich (240877)  p-Toluenesulfonylchloride  ReagentPlus®, ≥99% 98-59-9 240877-500G 7,031.70CNY Detail
Sigma-Aldrich (240877)  p-Toluenesulfonylchloride  ReagentPlus®, ≥99% 98-59-9 240877-100G 2,033.46CNY Detail
Sigma-Aldrich (240877)  p-Toluenesulfonylchloride  ReagentPlus®, ≥99% 98-59-9 240877-5G 459.81CNY Detail
Alfa Aesar (A14547)  p-Toluenesulfonyl chloride, 98%    98-59-9 5000g 2181.0CNY Detail
Alfa Aesar (A14547)  p-Toluenesulfonyl chloride, 98%    98-59-9 1000g 481.0CNY Detail
Alfa Aesar (A14547)  p-Toluenesulfonyl chloride, 98%    98-59-9 500g 268.0CNY Detail
Alfa Aesar (A14547)  p-Toluenesulfonyl chloride, 98%    98-59-9 250g 147.0CNY Detail
TCI America (T0272)  p-Toluenesulfonyl Chloride  >99.0%(GC) 98-59-9 500g 290.00CNY Detail
TCI America (T0272)  p-Toluenesulfonyl Chloride  >99.0%(GC) 98-59-9 25g 130.00CNY Detail

98-59-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name p-Toluenesulfonyl chloride

1.2 Other means of identification

Product number -
Other names 4-methylbenzenesulfonyl chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:98-59-9 SDS

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