133-59-5

Basic information

• Product Name: O-TOLUENESULFONYL CHLORIDE
• Synonyms: ortho-toluenesulfonylchloride;o-Toluenesulfochloride;o-tolylsulfonylchloride;o-Tosyl chloride;o-tosylchloride;toluene-2-sulphonylchloride;o-Toluenesulphonyl chloride;containsca23%isomer)75+%
• CAS NO: 133-59-5
• Molecular Formula: C₇H₇ClO₂S
• Molecular Weight: 190.65
• EINECS: 205-113-0
• Product Categories: Intermediates of Dyes and Pigments;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
• Mol File: 133-59-5.mol
• Article Data: 18

Chemical Properties

• Melting Point: 10°C
• Boiling Point: 254 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.320 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0102mmHg at 25°C
• Refractive Index: n20/D >1.5580(lit.)
• Storage Temp.: Store under inert gas
• Water Solubility: Soluble in hot alcohol, ether and benzene. Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 973180
• CAS DataBase Reference: O-TOLUENESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: O-TOLUENESULFONYL CHLORIDE(133-59-5)
• EPA Substance Registry System: O-TOLUENESULFONYL CHLORIDE(133-59-5)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 133-59-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 133-59-5 differently. You can refer to the following data:
1. o-Toluenesulfonyl chloride is used in organic synthesis and saccharin production. It is also used as pharmaceutical intermediate.
2. o-Toluenesulfonyl chloride may be used in the synthesis of:oxazolinemesityl o-tolyl sulfoneallyl o-toluenesulfonate2-methyl-4′-t-butyldiphenyl sulfone

General Description

o-Toluenesulfonyl chloride can be synthesized by reacting o-thiocresol in glacial acetic acid with chlorine. It participates in the preparation of 5-chloro-3-phenyl-2,1-benzisoxazole.

InChI:InChI=1/C7H7ClO2S/c1-6-4-2-3-5-7(6)11(8,9)10/h2-5H,1H3

Upstream product

• 108-88-3 toluene 
• 7790-94-5 chlorosulfonic acid 
• 7446-70-0 aluminium trichloride 
• 7705-08-0 iron(III) chloride 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 10026-13-8 phosphorus pentachloride 
• 88-20-0 o-toluenesulfonic acid 
• 7782-50-5 chlorine 
• 7719-12-2 phosphorus trichloride 
• 13165-77-0 toluenesulfinic acid 
• 7732-18-5 water 
• 16419-60-6 2-Methylphenylboronic acid 
• 88-19-7 methyl 2-(aminosulfonyl)benzoate 
• 127-65-1 chloroamine-T 

Downstream Products

• 56776-55-7 N-phenyl-S-(2-methylphenyl) sulfonamide 
• 41908-97-8 o-tolyl-p-tolyl sulfone 
• 13440-22-7 N-methyl(o-methyl)benzenesulfonamide 
• 7018-84-0 phenyl o-tolyl sulfone 
• 91252-35-6 N-Propyl-o-toluolsulfonamid 
• 66897-35-6 N-Allyl-N-(2-chloro-benzoyl)-2-methyl-benzenesulfonamide 
• 66897-70-9 N-Allyl-2-methyl-N-(1-methyl-1-phenyl-ethyl)-benzenesulfonamide 
• 55880-28-9 N-[2-(1,4-Dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yloxy)-ethyl]-2-methyl-N-phenyl-benzenesulfonamide 
• 105334-09-6 2-Methyl-benzenesulfonyl chloride; compound with dimethyl-phenyl-amine 
• 91832-69-8 1-Benzyl-3-toluenesulfonyloxypyrrolidine 
• 67448-06-0 N,N,2-trimethylbenzenesulfonamide 
• 130203-10-0 allyl o-toluenesulfonate 
• 54437-71-7 N-methyl-N-phenyl-2-methylbenzenesulfonamide 
• 21991-14-0 1,3,5-trimethyl-2-(o-tolylsulfonyl)benzene 

Relevant articles and documents

Preparation method of substituted benzene sulfonyl chloride

The invention provides a preparation method of substituted benzene sulfonyl chloride, which comprises the following steps: carrying out diazotization reaction on an aniline compound with a structure as shown in a formula I to obtain fluoboric acid diazonium salt with a structure as shown in a formula II; obtaining substituted benzene sulfonyl chloride with a structure as shown in a formula III from the fluoboric acid diazonium salt with the structure as shown in the formula II; wherein R is selected from any one of ortho-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano, acetyl, meta-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano, acetyl, para-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano and acetyl. The preparation method of the substituted benzene sulfonyl chloride provided by the invention is simple in reaction process, easy to operate, ideal in effect and suitable for industrial production.

Sulfonamide compound as well as preparation method and application thereof

The invention discloses a sulfonamide compound as well as a preparation method and application thereof. Three kinases including EGFR, VEGFR-2 and FGFR1 are used as targets; chalcone is used as a primer; an alpha,beta-unsaturated carbonyl conjugated struct

Propanolysis of arenesulfonyl chlorides: Nucleophilic substitution at sulfonyl sulfur

We have studied the mechanism of solvolysis of arenesulfonyl chlorides by propan-1-ol and propan-2-ol at 303-323 K. Kinetic profiles were appropriately fit by first-order kinetics. Reactivity increases with electron-donating substituents. Ortho-alkyl substituted derivatives of arenesulfonyl chlorides show increased reactivity, but the origin of this “positive” ortho-effect remains unclear. Likely, ortho-methyl groups restrict rotation around the C-S bond, facilitating the attack of the nucleophile. No relevant reactivity changes have been found with propan-1-ol and propan-2-ol in terms of nucleophile steric effect. The existence of isokinetic relationships for all substrates suggests a single mechanism for the series. Solvolysis reactions of all substrates in both alcohols show isokinetic temperatures (Tiso) close to the working temperature range, which is an evidence of the process being influenced by secondary reactivity factors, likely of steric nature in the TS. Solvation plays a relevant role in this reaction, modulating the reactivity. In some cases, the presence of t-Bu instead of Me in para- position leads to changes in the first solvation shell, increasing the energy of the reaction (ca. 1?kJ·mol?1). The obtained results suggest the same kinetic mechanism of solvolysis of arenesulfonyl chlorides for propan-1-ol and propan-2-ol, as in MeOH and EtOH, where bimolecular nucleophilic substitution (SN2) takes place with nucleophilic solvent assistance of one alcohol molecule and the participation of the solvent network involving solvent molecules of the first solvation shell.