Toluene-p-sulphonic anhydride

HCID 77773

Notes Reactions

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Basic information

CAS: 4124-41-8
Standard SMILES: Cc1ccc(S(=O)(=O)OS(=O)(=O)c2ccc(C)cc2)cc1
InChIKey: PDVFSPNIEOYOQL-UHFFFAOYSA-N
Molecular formula: C14H14O5S2
Average molar mass: 326.4 g/mol
Monoisotopic mass: 326.02826555

Names & identifiers

Preferred name: Toluene-p-sulphonic anhydride
IUPAC: (4-methylphenyl)sulfonyl 4-methylbenzenesulfonate
English name: P-Toluenesulfonic anhydride
Molecular formula: C14H14O5S2
Molecular weight: 326.38

Names & synonyms

p-Toluenesulfonic anhydride4124-41-8Toluene-p-sulphonic anhydrideEINECS 223-926-9DTXSID50194160RefChem:898585DTXCID60116651223-926-94-Methylbenzenesulfonic anhydride4-Toluenesulfonic anhydride(4-methylphenyl)sulfonyl 4-methylbenzenesulfonateMFCD00008548

Show more names

Tosic anhydridep-Tolylsulfonyl 4-methylbenzenesulfonateToluene-p-anhydride3-Toluenesulfonicanhydridep-Toluenesulfonyl anhydride

Benzenesulfonic acid, 4-methyl-, anhydrideP-Toluenesulfonicanhydridep-toluene sulfonic anhydrideToluene-4-sulfonic anhydride4-methylbenzenesulfonyl 4-methylbenzene-1-sulfonate4-Toluenesulfonic anhydride; Toluene-4-sulfonic acid ahnydride; Toluenesulfonic anhydride; Tosylic anhydride; p-Toluenesulfonic acid anhydride4-toluenesulfonic acid anhydridep-Toluenesulphonic anhydride

Database identifiers

CAS: 4124-41-8
PubChem CID: 77773
DTXSID: DTXSID50194160
EC Number: 223-926-9
Nikkaji: J224.933B

Properties

Computed structural properties

XLogP: 3.1
Topological polar surface area: 94.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 5
Rotatable bonds: 4
Heavy atoms: 21
Formal charge: 0
Complexity: 475

Physicochemical properties

Melting point: 121 · 121-127 °C(lit.)
Boiling point: 478 · 478.0±48.0 °C(Predicted)
Density: 1.361 · 1.361±0.06 g/cm3(Predicted)
storage temp.: 2 · Inert atmosphere,2-8°C
form: Powder, Crystals and/or Chunks
color: Off-white to gray
Sensitive: Moisture Sensitive
BRN: 2223702 · 2223702
InChI: 1S/C14H14O5S2/c1-11-3-7-13(8-4-11)20(15,16)19-21(17,18)14-9-5-12(2)6-10-14/h3-10H,1-2H3
InChIKey: PDVFSPNIEOYOQL-UHFFFAOYSA-N
SMILES: Cc1ccc(cc1)S(=O)(=O)OS(=O)(=O)c2ccc(C)cc2
CAS DataBase Reference: 4124 · 4124-41-8(CAS DataBase Reference)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 5 · GHS05
Signal word: Danger
Hazard statements: 314 · H314
Precautionary statements: 260 · P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363
PPE: 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes: C
Risk Statements: 34 · 34
Safety Statements: 26 · 26-36/37/39-45
RIDADR: 2585 · UN 2585 8/PG 3
WGK Germany: 3 · 3
F: 10 · 10-21
Hazard Note: Irritant
HazardClass: 8 · 8
PackingGroup: II
HS Code: 29041000 · 29041000
Storage Class: 8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications: 1 Skin · Eye Dam. 1Skin Corr. 1B

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

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

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

Aggregated GHS information provided per 53 reports by companies from 6 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Corr. 1C (100%)

Safety data

F: 10-21
PPE: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 3
ridadr: UN 2585 8/PG 3
hs_code: 29041000
risk_code: 34
Signal word: Danger
Symbol(GHS): GHS05
hazard_code: C
hazard_note: Irritant
safety_code: 26-36/37/39-45
hazard_class: 8
Storage Class: 8A - Combustible corrosive hazardous materials
packing_group: II
Hazard statements: H314
Hazard Classifications: Eye Dam. 1Skin Corr. 1B
Precautionary statements: P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363

Chemistry & industry

Applications

Usesp-Toluenesulfonic anhydride has been employed as reagent in palladium-catalyzed allylic alkenylation of allylic alcohols with n-butyl acrylate.

General Descriptionp-Toluenesulfonic anhydride acts as electrophilic species and activates 2-deoxy-sugar hemiacetals in situ, which reacts stereoselectively with nucleophilic acceptors to afford β-anomers.