P-Toluenesulfonyl chloride

Base Information

• Chemical Name: P-Toluenesulfonyl chloride
• CAS No.: 98-59-9
• Molecular Formula: C7H7ClO2S
• Molecular Weight: 190.65
• Hs Code.: 2904.90
• European Community (EC) Number: 202-684-8
• ICSC Number: 1762
• NSC Number: 175822
• UN Number: 1759
• UNII: 027KYN78B4
• DSSTox Substance ID: DTXSID1052660
• Nikkaji Number: J3.580G
• Wikipedia: 4-Toluenesulfonyl_chloride
• Wikidata: Q285621
• Mol file: 98-59-9.mol

Synonyms:4-toluenesulfonyl chloride;p-toluenesulfonyl chloride;tosyl chloride

Chemical Property of P-Toluenesulfonyl chloride

Chemical Property:

• Appearance/Colour: White to yellow solid
• Vapor Pressure: 1 mm Hg ( 88 °C)
• Melting Point: 65-69 °C(lit.)
• Refractive Index: 1.545
• Boiling Point: 265.3 °C at 760 mmHg
• Flash Point: 114.3 °C
• PSA: 42.52000
• Density: 1.339 g/cm³
• LogP: 3.00330
• Storage Temp.: Store at RT.
• Sensitive.: Moisture Sensitive
• Solubility.: methylene chloride: 0.2 g/mL, clear
• Water Solubility.: hydrolyses
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 189.9855283
• Heavy Atom Count: 11
• Complexity: 209
• Transport DOT Label: Corrosive

Purity/Quality:

98% ^*data from raw suppliers

4-Toluenesulfonyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C,Xi
• Statements: 34-29-41-38
• Safety Statements: 26-36/37/39-45-27-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)Cl
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes. The substance is irritating to the skin and respiratory tract.
• 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.
• Uses: Tosyl chloride (also known as p-Toluenesulfonyl chloride), is used as a precursor in the production of dyes and saccharin. It acts as a dehydrating agent in the conversion of urea to carbodiimide and converts alcohols into the corresponding toluenesulfonate esters. It is also employed as a flow-promoting agent for paints, an adhesive, nitrocellulose, coating material and as a plasticizer for polyamides. Furthermore, it serves as an antistatic agent, as a gloss enhancer in plastic film preparations and as a basic material of electroplating solutions.

Technology Process of P-Toluenesulfonyl chloride

There total 138 articles about P-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: 82.0%

1-Tosyl-1-<2-(4-methoxyphenyl)ethyl>hydrazine (141666-87-7) → p-toluenesulfonyl chloride (98-59-9) + 1-(2-Chloroethyl)-4-methoxybenzene (18217-00-0)

Guidance literature:

With N-chloro-succinimide; In tetrahydrofuran; for 16h; Ambient temperature; Irradiation;

DOI:10.1016/0040-4039(94)80009-X

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

Reference yield: 57.0%

1-p-Toluolsulfonyl-1-phenethyl-hydrazin (159690-31-0) → 2-phenylethyl chloride (622-24-2) + p-toluenesulfonyl chloride (98-59-9)

Guidance literature:

With N-chloro-succinimide; In tetrahydrofuran; for 16h; Ambient temperature; Irradiation;

DOI:10.1016/0040-4039(94)80009-X

upstream raw materials:

p-toluene sulfinic acid

p-methylbenzenediazonium chloride

sodium tosylate

toluene-4-sulfonic acid

Downstream raw materials:

methyl-[O²,O³,O⁶-tribenzoyl-O⁴-(toluene-4-sulfonyl)-β-D-glucopyranoside]

methyl-[O²,O³,O⁶-tribenzoyl-O⁴-(toluene-4-sulfonyl)-β-D-galactopyranoside]

methyl 2,3,6-tri-O-benzoyl-4-O-(p-tolylsulfonyl)-α-D-glucopyranoside

methyl-[O²,O³,O⁴-tribenzoyl-O⁶-(toluene-4-sulfonyl)-α-D-glucopyranoside]

Refernces

• 1、 Ikutani. "-". . p. 271. Retrieved 1971.
• 2、 -. "Method for continuously synthesizing P-toluenesulfonyl chloride". Paragraph 0089-0150. . Retrieved 2021/11/03.
• 3、 Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao. "Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides". . . Retrieved 2021/09/20.