ChemicalBook > Product Catalog > Organic Chemistry > Hydrocarbons and derivatives > Hydrocarbon sulfonate > Tosyl chloride
Basic information Tosyl chloride Chemical Properties Usage Production method Safety Related Supplier
Tosyl chloride Chemical 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 Reference98-59-9(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzenesulfonyl chloride, 4-methyl-(98-59-9)
- EPA Substance Registry Systemp-Toluenesulfonyl chloride (98-59-9)
- 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
- F 9-21
- Hazard Note Corrosive
- TSCA Yes
- HazardClass 8
- PackingGroup II
- HS Code 29049020
- Hazardous Substances Data98-59-9(Hazardous Substances Data)
- ToxicityLD50 orally in Rabbit: 4680 mg/kg
Tosyl chloride Usage And Synthesis
- Tosyl chlorideToluenesulfonyl 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 PropertiesWhite 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.
- Usage1. 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 methodToluene 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 PropertiesWhite to yellow solid
- UsesIt can be used for organic synthesis, for example: dyes, saccharin,etc.
- UsesTosyl chloride is mainly used in the preparation of chemical derivatives in the pharmaceutical, plastics and organic chemical industries.
- General DescriptionA 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 ReactionsInsoluble in water.
- Health HazardTOXIC; 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 HazardNon-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 allergensTosyl chloride is used mainly in the preparation of chemical derivatives in the pharmaceutical, plastics, and organic chemical industries.
- Purification MethodsMaterial 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
- Preparation Products1,5-Diazabicyclo[4.3.0]non-5-eneBENZYL GLYCIDYL ETHER5-Methyl-L-tryptophanBoc-L-beta-Homoproline1-(3-Dimethylaminopropyl)-3-ethylcarbodiimideAMITRAZ METABOLITE HYDROCHLORIDEMethyl 3-amino-4-phenylthiophene-2-carboxylateNORMEPERIDINE2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE(4S)-4-hydroxy-3-methyl-2-prop-2-ynyl-cyclopent-2-en-1-oneBenzo-15-crown-54-phenyl-1-(p-tolylsulphonyl)piperidine-4-carboxylic acid (3R)-(+)-3-(DIMETHYLAMINO)PYRROLIDINETracid Brilliant Red BTracid Brilliant Red 10bN,N'-BIS(ETHYLENE)-P-TOLUENESULFONAMIDE1-[(4-METHYLPHENYL)SULFONYL]-1H-INDOLE-3-CARBALDEHYDELevamisoleACID YELLOW 76 (C.I. 18850)1-IsoquinolinecarbonitrileN-Ethyl-p-toluenesulfonamideMethyl p-toluenesulfonateAcid Red 111P-TOLUENESULFONIC ACID N-OCTADECYL ESTERFAST RED B SALTACID ORANGE 63CHLORDIMEFORMAcid Orange 67N-Methyl-N-nitrosotoluene-4-sulphonamideN,N-BIS(2-CHLOROETHYL)-P-TOLUENESULFONAMIDE1-[(4-Methylphenyl)sulfonyl]-1H-imidazole2-CHLOROETHYL P-TOLUENESULFONATEEthyl p-toluenesulfonateACID RED 114Dodecyl 4-methylbenzenesulfonate4-Methylbenzenesulfonhydrazide2-Fluoroethyl 4-methylbenzenesulfonate4-MethylphenylsulfonylureaN-(p-Tolylsulphonyl)-L-glutamic acidBENPROPERINE
- Raw materialsTolueneChlorosulfonic acidBenzenesulfonyl chlorideO-TOLUENESULFONYL CHLORIDE
- N-Ethyl-p-toluenesulfonamide Tosyl chloride Sulfuryl chloride Benzyl chloride Methylene Chloride CHLORIDE STANDARD Ammonium chloride Toluene alpha-Toluenesulfonyl chloride p-Toluenesulfonamide METHYLSTYRENE Tosylmethyl isocyanide 4-Methylbenzenesulfonhydrazide 4-Nitrobenzenesulfonyl chloride 4-Methoxybenzenesulfonyl chloride 4-Chlorobenzenesulfonyl chloride Benzenesulfonyl chloride Sodium chloride
- Company Name:Nantong volan chemical co. LTD Gold
- Products Intro:CAS:98-59-9
- Company Name:Mei Lan Industrial (Shanghai) Co., Ltd. Gold
- Products Intro:Product Name:Tosyl chloride
- Company Name:Heze Kingvolt Chemical Co., Ltd Gold
- Tel:+86-15157335533 13505737768
- Products Intro:Product Name:P-Toluene Sulfonyl Chloride; PTSC; P-Toluenesulfonyl Chloride; Tosyl Chloride; Para Toluene Sulfonyl Chloride; P-Toluene Sulphonyl Chloride
- Company Name:Shanghai Aladdin Bio-Chem Technology Co.,LTD Gold
- Tel:400-620-6333 021-20337333-801
- Products Intro:Product Name:p-Toluenesulfonyl chloride(PTSC)
- Company Name:Shanghai Bojing Chemical Co., Ltd Gold
- Products Intro:Product Name:p-Toluenesulfonyl chloride