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Tosyl chloride

Tosyl chloride Chemical Properties Usage Production method
Tosyl chloride
Tosyl chloride
CAS No.
98-59-9
Chemical Name:
Tosyl chloride
Synonyms
PTSC;TsCl;TOS-CL;Tosylchlorid;TOSYL CHLORIDE;4-Tosyl chloride;p-tosyl chloride;p-toluenesulfonyl;AKOS BBS-00004428;4-toluene sulfonyl
CBNumber:
CB6328607
Molecular Formula:
C7H7ClO2S
Formula Weight:
190.65
MOL File:
98-59-9.mol

Tosyl chloride Properties

Melting point:
65-69 °C(lit.)
Boiling point:
134 °C10 mm Hg(lit.)
Density 
1,006 g/cm3
vapor pressure 
1 mm Hg ( 88 °C)
RTECS 
DB8929000
Flash point:
128 °C
storage temp. 
Store at RT.
solubility 
methylene chloride: 0.2 g/mL, clear
form 
Crystalline Powder
color 
White
Water Solubility 
hydrolyses
Sensitive 
Moisture Sensitive
Merck 
14,9534
BRN 
607898
Stability:
Stable. Substances to be avoided include strong bases and strong oxidizing agents and water. Moisture sensitive.
CAS DataBase Reference
98-59-9(CAS DataBase Reference)
NIST Chemistry Reference
Benzenesulfonyl chloride, 4-methyl-(98-59-9)
EPA Substance Registry System
Benzenesulfonyl chloride, 4-methyl-(98-59-9)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  C,Xi
Risk Statements  34-29-41-38
Safety Statements  26-36/37/39-45-27-39
RIDADR  UN 3261 8/PG 2
WGK Germany  1
9-21
Hazard Note  Corrosive
TSCA  Yes
HazardClass  8
PackingGroup  II
HS Code  29049020
Hazardous Substances Data 98-59-9(Hazardous Substances Data)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H314 Causes severe skin burns and eye damage Skin corrosion/irritation Category 1A, B, C Danger P260,P264, P280, P301+P330+ P331,P303+P361+P353, P363, P304+P340,P310, P321, P305+ P351+P338, P405,P501
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H318 Causes serious eye damage Serious eye damage/eye irritation Category 1 Danger P280, P305+P351+P338, P310
Precautionary statements:
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P303+P361+P353 IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405 Store locked up.

Tosyl chloride price More Price(16)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 240877 p-Toluenesulfonyl chloride ReagentPlus , ≥99% 98-59-9 5g $39.7 2018-11-13 Buy
Sigma-Aldrich 240877 p-Toluenesulfonyl chloride ReagentPlus , ≥99% 98-59-9 100g $144 2018-11-13 Buy
TCI Chemical T0272 p-Toluenesulfonyl Chloride >99.0%(GC) 98-59-9 25g $16 2018-11-22 Buy
TCI Chemical T0272 p-Toluenesulfonyl Chloride >99.0%(GC) 98-59-9 500g $36 2018-11-22 Buy
Alfa Aesar A14547 p-Toluenesulfonyl chloride, 98% 98-59-9 500g $34.9 2018-11-13 Buy

Tosyl chloride Chemical Properties,Uses,Production

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.

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.

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.

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.

Air & Water Reactions

Insoluble in water.

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.

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.

Contact allergens

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

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.]

Tosyl chloride Preparation Products And Raw materials

Raw materials

Preparation Products


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Tosyl chloride Spectrum


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