o-Toluenesulfonyl chloride

Base Information

• Chemical Name: o-Toluenesulfonyl chloride
• CAS No.: 133-59-5
• Molecular Formula: C7H7ClO2S
• Molecular Weight: 190.65
• Hs Code.: 2904909090
• European Community (EC) Number: 205-113-0
• NSC Number: 9354
• UNII: 341L82E3WG
• DSSTox Substance ID: DTXSID7051682
• Nikkaji Number: J134.588E
• Wikidata: Q27256316
• Mol file: 133-59-5.mol

Synonyms:o-Toluenesulfonyl chloride;133-59-5;2-Methylbenzenesulfonyl chloride;2-methylbenzene-1-sulfonyl chloride;2-Toluenesulfonyl chloride;Benzenesulfonyl chloride, 2-methyl-;Toluene-2-sulphonyl chloride;o-Tosyl chloride;O-TOLYLSULFONYL CHLORIDE;2-methyl-benzenesulfonyl chloride;ortho-Toluenesulfochloride;toluene-2-sulfonyl chloride;ortho-Toluenesulfonyl chloride;2-Methylbenzenesulphonyl chloride;Benzenesulfonyl chloride, methyl-;ortho-Toluenesulfonchloride;O-Toluenesulfonyl chloride, tech grade;UNII-341L82E3WG;2-methylphenylsulfonyl chloride;o-methylbenzenesulfonyl chloride;HSDB 5618;341L82E3WG;NSC 9354;NSC-9354;EINECS 205-113-0;MFCD00024874;2-methylbenzene-1-sulfonylchloride;tolylsulfonyl chloride;toluenesulfonylchloride;toluenesufonyl chloride;toluenesulphonylchloride;toluene sulfonylchloride;toluenesulfonic chloride;o-toluenesulfonylchloride;Toluene sulfonyl chloride;toluene sulphonyl chloride;toluene-sulphonyl chloride;Toluene suiphonyl chloride;SCHEMBL4439;toluenesulfonic acid chloride;toluenesulphonic acid chloride;toluene sulfonic acid chloride;DTXSID7051682;NSC9354;o-Toluenesulfonyl chloride, 97%;2-methylbenzene-sulphonyl chloride;BBL013805;STK500501;AKOS005207130;O-TOLYLSULFONYL CHLORIDE [HSDB];AM803157;PS-10915;BB 0253732;FT-0631774;T0284;EN300-66997;A806639;J-006410;Q27256316

Chemical Property of o-Toluenesulfonyl chloride

Chemical Property:

• Vapor Pressure: 0.0102mmHg at 25°C
• Melting Point: 10 °C
• Refractive Index: n20/D >1.5580(lit.)
• Boiling Point: 272.3 °C at 760 mmHg
• Flash Point: 118.5 °C
• PSA: 42.52000
• Density: 1.339g/cm³
• LogP: 3.00330
• Storage Temp.: Store under inert gas
• Sensitive.: Moisture Sensitive
• Water Solubility.: Soluble in hot alcohol, ether and benzene. Reacts with water.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 189.9855283
• Heavy Atom Count: 11
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

o-Toluenesulfonyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C， Xi
• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: CC1=CC=CC=C1S(=O)(=O)Cl
• Uses: o-Toluenesulfonyl chloride is used in organic synthesis and saccharin production. It is also used as pharmaceutical intermediate. o-Toluenesulfonyl chloride may be used in the synthesis of:oxazolinemesityl o-tolyl sulfoneallyl o-toluenesulfonate2-methyl-4′-t-butyldiphenyl sulfone

Technology Process of o-Toluenesulfonyl chloride

There total 29 articles about o-Toluenesulfonyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

N,N-diethylthiocarbamic acid S-o-tolyl ester (82125-34-6) → Toluene-2-sulfonyl chloride (133-59-5)

Guidance literature:

With chlorine; acetic acid; at 0 ℃;

Reference yield: 90.0%

1-Methoxymethylsulfanyl-2-methyl-benzene (64846-49-7) → Toluene-2-sulfonyl chloride (133-59-5)

Guidance literature:

With water; chlorine; In dichloromethane; at 5 - 10 ℃; for 1h;

DOI:10.1055/s-1992-26333

Reference yield: 80.0%

toluene (108-88-3,15644-74-3,16713-13-6) → p-toluenesulfonyl chloride (98-59-9) + Toluene-2-sulfonyl chloride (133-59-5)

Guidance literature:

With chlorosulfonic acid; sodium chloride; at -0.16 ℃;

DOI:10.1002/poc.3753

upstream raw materials:

toluenesulfinic acid

toluene

1-Methoxymethylsulfanyl-2-methyl-benzene

N,N-diethylthiocarbamic acid S-o-tolyl ester

Downstream raw materials:

toluene-2-sulfonic acid-(4-hydroxy-anilide)

N-(2-hydroxy-ethyl)-toluene-2-sulfonamide

toluene-2-sulfonic acid m-tolyl ester

N-(2-naphthyl)-p-toluenesulphonamide

Refernces

• 1、 -. "CHEMICAL COMPOUNDS". Paragraph 0173-0175. . Retrieved 2021/04/02.
• 2、 Gómez-Palomino, Alejandro,Cornella, Josep. "Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4". supporting information. p. 18235 - 18239. Retrieved 2019/11/13.