o-Toluenesulfonyl chloride

HCID 8623CAS 133-59-5

Substructure search Find similar structures

Basic information

Standard SMILES: Cc1ccccc1S(=O)(=O)Cl
InChIKey: HDECRAPHCDXMIJ-UHFFFAOYSA-N
Molecular formula: C7H7ClO2S
Average molar mass: 190.65 g/mol
Monoisotopic mass: 189.9855283

Names & identifiers

Preferred name: o-Toluenesulfonyl chloride
IUPAC: 2-methylbenzenesulfonyl chloride
English name: O-TOLUENESULFONYL CHLORIDE
Molecular formula: C7H7ClO2S
Molecular weight: 190.65

Names & synonyms

o-Toluenesulfonyl chloride133-59-52-Methylbenzenesulfonyl chloride2-methylbenzene-1-sulfonyl chlorideBenzenesulfonyl chloride, 2-methyl-Toluene-2-sulphonyl chloride2-Toluenesulfonyl chlorideo-Tosyl chlorideO-TOLYLSULFONYL CHLORIDE2-Methylbenzenesulphonyl chloride2-methyl-benzenesulfonyl chlorideortho-Toluenesulfochloride

Show more names

o-Toluenesulfochlorideo-tosylchlorideParoxetine Impurity 30o-tolylsulfonylchloridecontainsca23%isomer)75+%

toluene-2-sulfonyl chlorideortho-Toluenesulfonyl chlorideMFCD000248742-methylphenylsulfonyl chlorideo-methylbenzenesulfonyl chloride341L82E3WGNSC-9354o-Toluenesulfonyl Chloride (contains ca. 23% isomer)

Database identifiers

CAS: 133-59-5、26763-71-3
PubChem CID: 8623
DTXSID: DTXSID7051682
UNII: 341L82E3WG
EC Number: 205-113-0、247-990-2
Nikkaji: J134.588E

Properties

Computed structural properties

XLogP: 2.3
Topological polar surface area: 42.5 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 11
Formal charge: 0
Complexity: 217

Experimental & physicochemical properties

Density1.3383 AT 20 °C/4 °C

Color/FormOILY LIQUID

Solubility · 2 items

INSOL IN WATER

SOL IN HOT ALCOHOL, BENZENE, ETHER

Boiling Point154 °C AT 36 MM HG

Melting Point10.2 °C

Refractive IndexSADTLER REF NUMBER: 10657 (IR, PRISM); INDEX OF REFRACTION: 1.5565 AT 20 °C/D

Physicochemical properties

Melting point: 10 °C · 10°C
Boiling point: 254 °C · 254 °C(lit.)
Density: 1.32 g/mL · 1.320 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D >1.5580(lit.)
Flash point: 230 °F · >230 °F
storage temp.: Store under inert gas
solubility: Acetonitrile (Slightly), Chloroform(Slightly)
form: clear liquid
color: Colorless to Light yellow
Water Solubility: Soluble in hot alcohol, ether and benzene. Reacts with water.
Sensitive: Moisture Sensitive
BRN: 973180 · 973180
InChI: InChI=1S/C7H7ClO2S/c1-6-4-2-3-5-7(6)11(8,9)10/h2-5H,1H3
InChIKey: HDECRAPHCDXMIJ-UHFFFAOYSA-N
SMILES: C1(S(Cl)(=O)=O)=CC=CC=C1C
CAS DataBase Reference: 133 · 133-59-5(CAS DataBase Reference)
FDA UNII: 341 L82E3WG · 341L82E3WG
EPA Substance Registry System: 2 · Benzenesulfonyl chloride, 2-methyl- (133-59-5)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 5 · GHS05
Signal word: Danger
Hazard statements: 314 · H314-H290
Precautionary statements: 501 · P501-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes: C,Xi
Risk Statements: 34 · 34
Safety Statements: 26 · 26-36/37/39-45
RIDADR: 3265 · UN 3265 8/PG 2
WGK Germany: 3 · 3
Hazard Note: Corrosive
TSCA: TSCA listed
HazardClass: 8 · 8
PackingGroup: II
HS Code: 2904100090 · 2904100090
Storage Class: 8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications: 1 B · Skin Corr. 1B
Hazardous Substances Data: 133 · 133-59-5(Hazardous Substances Data)

Safety & regulation

GHS classification

GHS Classification · 5 items

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]；H318 (76.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 52 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazards SummaryReacts with water; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; [MSDSonline]

Hazard Classes and CategoriesSkin Corr. 1C (100%)；Eye Dam. 1 (76.9%)

Toxicology

Adverse EffectsDermatotoxin - Skin burns.；Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

Safety data

PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
ridadr: UN 3265 8/PG 2
hs_code: 2904100090
risk_code: 34
Signal word: Danger
Symbol(GHS): GHS05
hazard_code: C,Xi
hazard_note: Corrosive
safety_code: 26-36/37/39-45
hazard_class: 8
Storage Class: 8A - Combustible corrosive hazardous materials
packing_group: II
Hazard statements: H314-H290
Hazard Classifications: Skin Corr. 1B
Precautionary statements: P501-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405
Hazardous Substances Data: 133-59-5(Hazardous Substances Data)

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as intermediate in the synthesis of saccharin and dyestuffs; [HSDB]

INTERMEDIATE IN SYNTHESIS OF SACCHARIN & DYESTUFFS

Methods of ManufacturingACTION OF CHLOROSULFONIC ACID ON TOLUENE.

General Manufacturing InformationBenzenesulfonyl chloride, 2-methyl-: ACTIVE

Applications · 3 items

Useso-Toluenesulfonyl chloride is used in organic synthesis and saccharin production. It is also used as pharmaceutical intermediate.

Useso-Toluenesulfonyl chloride may be used in the synthesis of:oxazolinemesityl o-tolyl sulfoneallyl o-toluenesulfonate2-methyl-4′-t-butyldiphenyl sulfone

General Descriptiono-Toluenesulfonyl chloride can be synthesized by reacting o-thiocresol in glacial acetic acid with chlorine. It participates in the preparation of 5-chloro-3-phenyl-2,1-benzisoxazole.