4-Toluenesulfonyl chloride
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Basic information
- CAS
98-59-9- Standard SMILES
Cc1ccc(S(=O)(=O)Cl)cc1- InChIKey
YYROPELSRYBVMQ-UHFFFAOYSA-N- Molecular formula
- C7H7ClO2S
- Average molar mass
- 190.65 g/mol
- Monoisotopic mass
- 189.9855283
Overview
P-toluene sulfonylchloride appears as a 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.
Names & identifiers
- Preferred name
- 4-Toluenesulfonyl chloride
- IUPAC
- 4-methylbenzenesulfonyl chloride
- English name
- Tosyl chloride
- Molecular formula
- C7H7ClO2S
- Molecular weight
- 190.65
Names & synonyms
4-Toluenesulfonyl chlorideRefChem:169391P-TOLUENESULFONYL CHLORIDE98-59-9Tosyl chloride4-Methylbenzenesulfonyl chloridep-Tosyl chloride4-methylbenzene-1-sulfonyl chloridep-Toluenesulphonyl chloridep-Tolylsulfonyl chloridep-Toluenesulfochloridep-Toluenesulfonic acid chloride
Show more names
TsClTOS-CLPTSCPARA TOLUENE SULFONYL CHLORIDEp-toluenesulfonyl
tosylchloridep-Methylbenzenesulfonyl chloridepara-Toluenesulfonyl chloride4-Tosyl chlorideBenzenesulfonyl chloride, 4-methyl-4-toluene sulfonyl chloridep-Toluene sulphonyl chlorideToluenesulfonyl chloride
Database identifiers
- CAS
98-59-9- PubChem CID
- 7397
- DTXSID
DTXSID1052660- UNII
- 027KYN78B4
- EC Number
- 202-684-8
- Nikkaji
- J3.580G
Properties
Computed structural propertiesFilling in
- XLogP
- 3
- Topological polar surface area
- 42.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 209
Experimental & physicochemical properties
Chemical ClassesToxic Gases & Vapors -> Acid Halides
SpringerMaterials PropertiesSchoenflies notation
LogP
3.49
3.25
Density
1.3 g/cm³
1.33 @25 °C
Color/Form
CRYSTALS
TRICLINIC CRYSTALS FROM ETHER OR PETROLEUM ETHER
Solubility
INSOL IN WATER; FREELY SOL IN ALCOHOL, BENZENE, ETHER
Solubility in water: reaction
Flash Point128 °C c.c.
Boiling Point146 °C @ 15 MM HG
Melting Point
69-71 °C
69-71 °C
Vapor Density
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 5.7% (53 of 926) of reports.
Danger
H290 (20%): May be corrosive to metals [Warning Corrosive to Metals]
P234, P260, P261, P264, P264+P265, P271, P272, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P332+P317, P333+P317, P362+P364, P363, P390, P403+P233, P405, P406, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 926 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzenesulfonyl chloride, 4-methyl-
REACH registered substance: Tosyl chloride (EC: 202-684-8)
4-Toluenesulphonyl chloride: Does not have an individual approval but may be used under an appropriate group standard
DOT LabelCorrosive
Fire Hazards
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Hazards Summary
A skin, eye, and respiratory tract irritant; [HSDB] Reacts violently with water evolving hydrochloric acid; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; [MSDSonline] Slowly hydrolyzes to strong acids (HCl and p-toluenesulfonic acid); Severely irritating to skin and eyes in animal testing; [AIHA] Contact dermatitis documented in a chemist; [Kanerva, p. 1841]
Chemistry & industry
Uses & manufacturing
Uses
Used to make other organic chemicals; [Hawley] Used to make food additives, foaming agents for plastics and rubber, riboflavin, antithrombotic drugs, and dye condensing agents; [eChemPortal: SIDSUNEP]
ORGANIC SYNTHESIS
Methods of ManufacturingMADE BY TREATING TOLUENE WITH CHLOROSULFONIC ACID.
General Manufacturing Information
Benzenesulfonyl chloride, 4-methyl-: ACTIVE
10 OF 16 MERCURATED SULFONAMIDES TESTED AS BACTERICIDES & FUNGICIDES AGAINST E COLI, RHIZOCTONIA SOLANI, S AUREUS, A NIGER, & CHETOMIUM GLOBOSSUM WERE MORE TOXIC THAN ZINEB. SULFONAMIDES PREPD BY CONDENSING ANILINE BASE WITH P-TOLUENESULFONYL CHLORIDE IN PRESENCE OF PYRIDINE + BENZENE.
Applications
UsesTosyl 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.
General DescriptionTosyl chloride is a white to gray powdered solid with a distinctive odor. It can be used in organic synthesis, to make nitriles, isocyanides and diimides.
Preparation methods
PreparationTosyl 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
Related reactions
7,091 records
Compound notes
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