CAS 4083-64-1 p-Toluenesulfonyl isocyanate (HCID 77703)

Names & identifiers

Preferred name: p-Toluenesulfonyl isocyanate
IUPAC: 4-methyl-N-(oxomethylidene)benzenesulfonamide
English name: p-Toluenesulfonyl Isocyanate
Molecular formula: C8H7NO3S
Molecular weight: 197.21

Names & synonyms

Tosyl isocyanatep-Toluenesulfonyl isocyanate4083-64-1p-Toluenesulphonyl isocyanate4-Methylbenzenesulfonyl isocyanateBenzenesulfonyl isocyanate, 4-methyl-DTXSID1027558Additive tiH9004FJX6VDTXCID407558RefChem:1094233223-810-8

Show more names

4-TOLUENESULFONYL ISOCYANATEPtslMSI/PTSIPOLYLINK PTSIPARA-TOSYLISOCYANATETOSYL ISOCYANATE (PTSI)

4-methyl-N-(oxomethylidene)benzenesulfonamidePtSip-Tolylsulfonyl isocyanate4-methylbenzene-1-sulfonyl isocyanatep-toluenesulfonylisocyanatep-Toluenesulfonic acid, anhydride with isocyanic acidp-Tosyl isocyanatep-Methylphenylsulfonyl isocyanate

Database identifiers

CAS: 4083-64-1
PubChem CID: 77703
DTXSID: DTXSID1027558
ChEMBL: CHEMBL1879981
UNII: H9004FJX6V
EC Number: 223-810-8
Nikkaji: J195C

Properties

Computed structural properties

XLogP: 2.7
Topological polar surface area: 72 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 13
Formal charge: 0
Complexity: 303

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)

SpringerMaterials PropertiesX-ray diffraction

Physical Description · 2 items

Liquid

Colorless liquid with an irritating odor; [Alfa Aesar MSDS]

Physicochemical properties

Melting point: 5 °C · 5°C
Boiling point: 144 °C10 · 144 °C10 mm Hg(lit.)
Density: 1.291 g/mL · 1.291 g/mL at 25 °C(lit.)
vapor pressure: 1 mm · 1 mm Hg ( 100 °C)
refractive index: 20 · n20/D 1.534(lit.)
Flash point: 230 °F · >230 °F
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
form: Liquid
color: Clear colorless to yellow
Specific Gravity: 1.291 · 1.291.291
Odor: acrid odor
Water Solubility: reacts
Sensitive: Moisture Sensitive
BRN: 391287 · 391287
Henry's Law Constant: 1.7 · 1.7×10-1 mol/(m3Pa) at 25℃, Zhang et al. (2010)
InChI: 1S/C8H7NO3S/c1-7-2-4-8(5-3-7)13(11,12)9-6-10/h2-5H,1H3
InChIKey: VLJQDHDVZJXNQL-UHFFFAOYSA-N
SMILES: Cc1ccc(cc1)S(=O)(=O)N=C=O
LogP: 0.6 at · 0.6 at 30℃
CAS DataBase Reference: 4083 · 4083-64-1(CAS DataBase Reference)
FDA UNII: 9004 FJX6V · H9004FJX6V
NIST Chemistry Reference: 4 · 4-Methylbenzenesulfonyl isocyanate(4083-64-1)
EPA Substance Registry System: 4 · Benzenesulfonyl isocyanate, 4-methyl- (4083-64-1)
UNSPSC Code: 41116105 · 41116105
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07,GHS08
Signal word: Danger
Hazard statements: 315 · H315-H319-H334-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
Hazard Codes: Xn
Risk Statements: 14 · 14-36/37/38-42
Safety Statements: 26 · 26-28-30-28A
RIDADR: 2206 · UN 2206 6.1/PG 3
WGK Germany: 1 · 1
RTECS: 9032000 · DB9032000
F: 10 · 10
TSCA: TSCA listed
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29309090 · 29309090
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 2 Resp · Eye Irrit. 2Resp. Sens. 1Skin Irrit. 2STOT SE 3
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P233, P260, P261, P264, P264+P265, P271, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.3% (2 of 668) of reports.

Danger

H315 (99.7%): Causes skin irritation [Warning Skin corrosion/irritation]

Hazard information

Regulatory Information · 5 items

Chemical: Benzenesulfonyl isocyanate, 4-methyl-

Hazard Traits - Respiratory Toxicity

Benzenesulfonyl isocyanate, 4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenesulfonyl isocyanate, 4-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 02-06-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/10026

4-Toluenesulphonyl isocyanate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Isocyanates: Human health tier II assessment

Hazards Summary · 1 item

A mild skin and moderate eye irritant; Causes changes in leukocyte count and changes in liver and kidney weights in 42-day constant oral studies of rats; [RTECS] Highly reactive; Hydrolyses rapidly forming p-toluenesulfonamide (CAS# 70-55-3) and carbon dioxide; [EPA ChAMP: Submission] Reacts violently with water; A skin and strong eye irritant; May cause respiratory sensitization; [Alfa Aesar MSDS] Search for (4083-64-1[EC/RN Number]) AND (asthma OR dermatitis OR allergic OR sensitizer OR sensitization): no results; [PubMed] See p-Toluenesulfonamide.

Hazard Classes and Categories · 3 items

Skin Irrit. 2 (99.7%)

Acute toxicity - category 1

STOT SE 3

CSL Reaction Information · 6 items

CSL00164

p-Toluenesulfonyl isocyanate + Water

Reaction resulted in a fire

Flammable

Not Available

User Reported

Toxicology

Toxicity DataLC50 (rat) > 640 ppm/1hr

Safety data

F: 10
wgk: 1
tsca: TSCA listed
rtecs: DB9032000
ridadr: UN 2206 6.1/PG 3
hs_code: 29309090
risk_code: 14-36/37/38-42
Signal word: Danger
Symbol(GHS): GHS07,GHS08
hazard_code: Xn
safety_code: 26-28-30-28A
hazard_class: 6.1
Storage Class: 10 - Combustible liquids
packing_group: III
target organs: Respiratory system
Hazard statements: H315-H319-H334-H335
REACH Registrations: Active
Hazard Classifications: Eye Irrit. 2Resp. Sens. 1Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used in polyurethane coatings, sealants, and adhesives, as a stabilizer for organic isocyanates, and as a chemical intermediate; [EPA ChAMP: Submission] Used to formulate adhesives-sealants and paints-coatings-thinners and as an intermediate for pharmaceuticals; [ExPub: ECHA REACH Registrations]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

U.S. Production2023: 1,000,000 - <2,500,000 lb

Consumer UsesDehydrating agent (desiccant)

Industry UsesAdhesion/cohesion promoter

General Manufacturing Information · 2 items

Paint and Coating Manufacturing

Benzenesulfonyl isocyanate, 4-methyl-: ACTIVE

Applications · 3 items

UsesIt is a reagent used to prepare acetylated syn-1,2-diols,oxazolidin-2-ones, 2,3-diamino acids, and N-tosylcarbonamides. -Toluenesulfonyl isocyanate has been used as derivatization reagent in determination of 3-α-hydroxy tibolone in human plasma by LC-MS/MS. It is also employed in the derivatization reagent in simultaneous quantitative analysis of diethylene glycol and propylene glycol in pharmaceutical products by HPLC and as reagent in the preparation of acetylated syn-1,2-diols, oxazolidin-2-ones, 2,3-diamino acids and N-tosylcarbonamides.

Usesp-Toluenesulfonyl isocyanate is a reagent used to prepare acetylated syn-1,2-diols,1 oxazolidin-2-ones,2 2,3-diamino acids,3 and N-tosylcarbonamides.4

General Descriptionp-Toluenesulfonyl isocyanate undergoes palladium-catalyzed bis-allylation reaction with allylstannanes and allyl chlorides.