98-59-9 Usage
Chemical Description
Tosyl chloride is a colorless liquid that is commonly used as a reagent in organic synthesis to introduce the tosyl (Ts) functional group (-SO2C6H4CH3) into organic molecules.
Chemical Description
Tosyl chloride is used to tosylate the free hydroxyl group of a compound.
Description
Tosyl chloride, also known as p-Toluenesulfonyl chloride, is an organic compound that serves as a versatile reagent and intermediate in various chemical reactions and industries.
Uses
Used in Chemical Synthesis:
Tosyl chloride is used as a precursor in the production of dyes and saccharin, playing a crucial role in the synthesis of these compounds.
Used in Dehydration Processes:
Tosyl chloride acts as a dehydrating agent in the conversion of urea to carbodiimide, facilitating the reaction and enhancing the yield of the desired product.
Used in Organic Chemistry:
Tosyl chloride converts alcohols into the corresponding toluenesulfonate esters, which are important intermediates in organic synthesis and can be used for further reactions.
Used in Paint and Coating Industry:
Tosyl chloride is employed as a flow-promoting agent for paints, improving their application properties and ensuring a smooth and even finish.
Used in Adhesive and Nitrocellulose Production:
Tosyl chloride serves as an adhesive and a component in nitrocellulose production, contributing to the bonding properties and performance of these materials.
Used in Plasticizer Industry:
Tosyl chloride is used as a plasticizer for polyamides, enhancing the flexibility and processability of these polymers.
Used in Antistatic and Gloss Enhancement Applications:
Tosyl chloride functions as an antistatic agent and a gloss enhancer in plastic film preparations, improving the surface properties and reducing the buildup of static charge.
Used in Electroplating Solutions:
Tosyl chloride serves as a basic material in electroplating solutions, contributing to the efficiency and quality of the electroplating process.
Tosyl chloride
Tosyl 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 lookchem.
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.
Preparation
Tosyl chloride is a by-product from the production of ortho-toluenesulfonyl chloride (a precursor for the synthesis of the common food additive and catalyst saccharin), via the chlorosulfonation of toluene:CH3C6H5+ SO2Cl2→ CH3C6H4SO2Cl + HCl
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.
Flammability and Explosibility
Nonflammable
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 98-59-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 8 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 98-59:
(4*9)+(3*8)+(2*5)+(1*9)=79
79 % 10 = 9
So 98-59-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3
98-59-9Relevant articles and documents
Facile synthesis of sulfonyl chlorides
Huang, Jianxing,Widlanski, Theodore S.
, p. 2657 - 2660 (1992)
A method for the synthesis of sulfonyl chlorides and bromides from the corresponding sulfonate salts is described. The method gives good yields of the acid halides under very mild conditions, and is compatible with both acid and base sensitive functionalities.
Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts
Chen, Guang-Le,He, Shi-Hui,Cheng, Liang,Liu, Feng
supporting information, p. 8338 - 8342 (2021/10/25)
We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.
Method for continuously synthesizing P-toluenesulfonyl chloride
-
Paragraph 0089-0150, (2021/11/03)
The method comprises the following steps: toluene, sulfur trioxide, chlorosulfonic acid, an organic base and a solvent are mixed in first static mixers, and then pumped into first microreactors to react. The first Micro-reactor outlet discharged first reaction mixture flows into second static mixer and mixed with sulfur trioxide, chlorosulfonic acid, low carbon chain fatty acid and solvent pumped into second static mixers respectively, and the resulting mixed materials are pumped into second microreactors to react. The second The secondary reaction mixture discharged from the microreactor was cooled, crystallized and isolated to yield p-toluenesulfonyl chloride as a product. To the method, the production efficiency is greatly improved; due to the addition of the sulfone inhibitor, the problems that a large amount of sulfone substances and polysulfonate are easily generated by sulfonation of sulfur trioxide are effectively solved, and hydrogen chloride gas is prevented from being generated.
Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
, (2021/09/20)
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.