4-methylbenzenesulfonyl 4-methylbenzene-1-sulfonate

• ChemBase ID: 70090
• Molecular Formular: C14H14O5S2
• Molecular Mass: 326.38796
• Monoisotopic Mass: 326.02826555
• SMILES: c1(ccc(cc1)C)S(=O)(=O)OS(=O)(=O)c1ccc(cc1)C
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)OS(=O)(=O)c1ccc(cc1)C
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methylbenzenesulfonyl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: 4-methylbenzenesulfonyl 4-methylbenzenesulfonate
• Synonyms: p-Toluenesulfonic anhydride; p-Toluenesulfonic anhydride; p-Toluenesulphonic anhydride; 4-Toluenesulphonic anhydride; 4-Methylbenzenesulfonic anhydride; Tosic anhydride; 对甲苯磺酸酐

Database IDs

• CAS Number: 4124-41-8
• EC Number: 223-926-9
• MDL Number: MFCD00008548
• Beilstein Number: 2223702
• PubChem SID: 24889270; 162035815; 24855433
• PubChem CID: 77773

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.933453
• LogD (pH = 7.4): 3.933453
• Log P: 3.933453
• Molar Refractivity: 79.6644 cm^3
• Polarizability: 32.450256 Å^3
• Polar Surface Area: 77.51 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 121-127 °C(lit.); 121-130°C; 122-132 °C; 125-130°C

Safety Information

• Storage Warning: Corrosive/Moisture Sensitive/Store under Argon; IRRITANT; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 2585; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3; III
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: false; 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2585 8/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (NT); 95+%; 97%
• Grade: purum
• Linear Formula: (CH3C6H4SO2)2O

DETAILS

Sigma Aldrich - 259764

Packaging
5, 25 g in glass bottle

REFERENCES

• More powerful sulfonylating reagent than the sulfonyl chloride, also avoiding possible displacement of sulfonate by halide. This is particularly useful in the sulfonylation of hindered alcohols and sugars: J. Chem. Soc., 1225 (1953).
• Anions of ?-ketoesters react with p-toluenesulfonic anhydride to give enol tosylates in good yield; tosyl chloride gives poor results (ca 20%): Synth. Commun., 20, 881 (1990).
• Has been used in combination with Paraformaldehyde, A11313 in the generation of monomeric formaldehyde: Synlett, 704 (1990).