Basic information
- Standard SMILES
Cc1ccc(S(=O)(=O)Cl)cc1- InChIKey
YYROPELSRYBVMQ-UHFFFAOYSA-N- Molecular formula
- C7H7ClO2S
- Average molar mass
- 190.65 g/mol
- Monoisotopic mass
- 189.98552814
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-Toluenesulfochloridetosylchloride
Show more names
TsClTOS-CLPTSCPARA TOLUENE SULFONYL CHLORIDEp-toluenesulfonyl
p-Toluenesulfonic acid chloridep-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 properties
- 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
LogP3.49
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 DensityRelative vapor density (air = 1): 6.6
Vapor Pressure
Vapor pressure, Pa at 25 °C: 0.16
1 [mm Hg] @88 °C
Physical Description
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.
A white to gray solid; [CAMEO] Hygroscopic; [eChemPortal: SIDSUNEP] White or light yellow crystalline solid; [MSDSonline]
COLOURLESS-TO-YELLOW HYGROSCOPIC CRYSTALS WITH PUNGENT ODOUR.
Physicochemical properties
- Melting point
- 65 · 65-69 °C(lit.)
- Boiling point
- 134 °C10 · 134 °C10 mm Hg(lit.)
- Density
- 1 · 1,006 g/cm3
- bulk density
- 800 kg/m3 · 800kg/m3
- vapor pressure
- 1 mm · 1 mm Hg ( 88 °C)
- RTECS
- 8929000 · DB8929000
- Flash point
- 128 °C · 128 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 0.2 g/mL, · methylene chloride: 0.2 g/mL, clear
- form
- Crystalline Powder
- color
- White
- Water Solubility
- hydrolyses
- Sensitive
- Moisture Sensitive
- Merck
- 14 · 14,9534
- BRN
- 607898 · 607898
- Henry's Law Constant
- 1 · 1.0×100 mol/(m3Pa) at 25℃, Zhang et al. (2010)
- Stability
- Stable. Substances to be avoided include strong bases and strong oxidizing agents and water. Moisture sensitive.
- InChI
- 1S/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3
- InChIKey
- YYROPELSRYBVMQ-UHFFFAOYSA-N
- SMILES
- Cc1ccc(cc1)S(Cl)(=O)=O
- CAS DataBase Reference
- 98 · 98-59-9(CAS DataBase Reference)
- FDA UNII
- 27 KYN78B4 · 027KYN78B4
- NIST Chemistry Reference
- 4 · Benzenesulfonyl chloride, 4-methyl-(98-59-9)
- EPA Substance Registry System
- p-Toluenesulfonyl chloride (98-59-9)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314-H402-H290
- Precautionary statements
- 501 · P501-P273-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- C,Xi
- Risk Statements
- 34 · 34-29-41-38
- Safety Statements
- 26 · 26-36/37/39-45-27-39
- RIDADR
- 3261 · UN 3261 8/PG 2
- WGK Germany
- 1 · 1
- F
- 9 · 9-21
- Hazard Note
- Corrosive
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- II
- HS Code
- 29049020 · 29049020
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 1 Met · Eye Dam. 1Met. Corr. 1Skin Irrit. 2Skin Sens. 1
- Hazardous Substances Data
- 98 · 98-59-9(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: 4680 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 1 Kg · 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
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-
Status: Active Update: 12-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/13242
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]
Reactive GroupAcyl Halides, Sulfonyl Halides, and Chloroformates
UN ClassificationUN Hazard Class: 8; UN Pack Group: II
Chemical DangersDecomposes on heating. This produces toxic and corrosive fumes including sulfur oxides and hydrogen chloride. Reacts with water and moist air. This produces hydrogen chloride (see ICSC 0163).
Packaging and LabellingUnbreakable packaging. Put breakable packaging into closed unbreakable container.
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesMet. Corr. 1 (20%)
Safety & protection
Fire Fighting
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Use dry powder, carbon dioxide. NO water. NO foam.
First Aid Measures
Fresh air, rest.
Remove contaminated clothes. Rinse skin with plenty of water or shower.
Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.
Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .
First AidExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Safe StorageDry. Well closed. Store in an area without drain or sewer access.
Nonfire Spill ResponseExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Spillage Disposal
Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into containers. Carefully collect remainder. Then store and dispose of according to local regulations.
Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Eye PreventionWear safety goggles or eye protection in combination with breathing protection if powder.
Fire PreventionNO open flames.
Inhalation RiskA harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
Skin PreventionProtective gloves.
Exposure PreventionPREVENT DISPERSION OF DUST!
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Signs and Symptoms
Cough.
Redness. Pain.
Redness. Pain.
Sore throat.
ICSC Environmental DataThe substance is harmful to aquatic organisms.
Human Toxicity Excerpts
...PRODUCE SEVERE PRIMARY IRRITATION OF EYES, SKIN, OR RESP TRACT. DELAYED VESICATION IS NOT UNCOMMON. SENSITIZATION MAY ALSO OCCUR... /ACID HALIDES/
STRONG IRRITANT & VESICANT. /FROM TABLE/
WHILE CUMULATIVE TOXIC EFFECTS ARE THEORETICALLY POSSIBLE IF ORIGINAL ORG ACID IS ALSO KNOWN TO BE CUMULATIVE IN ACTION...IRRITANT PROPERTIES OF THE HALIDE PREVENT VOLUNTARY EXPOSURE TO SIGNIFICANT AMOUNTS... /ACID HALIDES/
Non-Human Toxicity Excerpts
REMSEN FAHLBERG SACCHARIN & ITS CONTAMINANTS (O-TOLUENE SULFONAMIDE (OTS), P-TOLUENE SULFONAMIDE (PTS), O-SULFAMOYL BENZOIC ACID, P-SULFAMOYL BENZOIC ACID) WERE TESTED FOR MUTAGENICITY. CONTAMINANTS OTS & ITS ISOMER PTS WERE MUTAGENIC IN AMES TEST & BASC TEST IN DROSOPHILA.
Safety data
- F
- 9-21
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- UN 3261 8/PG 2
- hs_code
- 29049020
- Toxicity
- LD50 orally in Rabbit: 4680 mg/kg
- risk_code
- 34-29-41-38
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C,Xi
- hazard_note
- Corrosive
- safety_code
- 26-36/37/39-45-27-39
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- II
- Hazard statements
- H314-H402-H290
- Limited Quantities
- 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Eye Dam. 1Met. Corr. 1Skin Irrit. 2Skin Sens. 1
- Precautionary statements
- P501-P273-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405
- Hazardous Substances Data
- 98-59-9(Hazardous Substances Data)
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
Upstream & downstream products
Upstream raw materials
Downstream products
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