4-methylbenzene-1-sulfonic acid; pyridine

• ChemBase ID: 149953
• Molecular Formular: C12H13NO3S
• Molecular Mass: 251.30152
• Monoisotopic Mass: 251.06161428
• SMILES: Cc1ccc(cc1)S(=O)(=O)O.c1ccncc1
• Canonical SMILES: c1cccnc1.Cc1ccc(cc1)S(=O)(=O)O
• InChI: InChI=1S/C7H8O3S.C5H5N/c1-6-2-4-7(5-3-6)11(8,9)10;1-2-4-6-5-3-1/h2-5H,1H3,(H,8,9,10);1-5H
• InChIKey: ZDYVRSLAEXCVBX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methylbenzene-1-sulfonic acid; pyridine
• IUPAC Traditional name: pyridine; toluenesulfonic acid
• Synonyms: PPTS; p-Toluenesulfonic acid pyridine salt; Pyridine p-toluenesulfonate; Pyridinium p-toluenesulfonate; 对甲苯磺酸 吡啶盐; 对甲苯磺酸吡啶盐; 吡啶对甲苯磺酸盐

Database IDs

• CAS Number: 24057-28-1
• EC Number: 246-002-7
• MDL Number: MFCD00013108
• Beilstein Number: 3764305
• PubChem SID: 162244115; 24888052; 24853887
• PubChem CID: 161440

CALCULATED PROPERTIES

• Acid pKa: -2.1372879
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.7088225
• LogD (pH = 7.4): -0.7088248
• Log P: 1.6675739
• Molar Refractivity: 41.7217 cm^3
• Polarizability: 16.707253 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 118-120 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (T); 98%
• Grade: puriss.
• Empirical Formula (Hill Notation): C12H13NO3S

DETAILS

Sigma Aldrich - 232238

Application
As a co-catalyst with L-proline improved both yield and enantioselectivity of an asymmetric aldol condensation between dioxanones and aldehydes.1
Efficient catalyst for the preparation of tetrahydropyranyl ethers (for OH-protection using DHP, cat. no. D106208).
Packaging
25, 100, 500 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 82815

Other Notes
Mild and efficient catalyst for the formation and cleavage of acetals1,2,3,4,5,6,7; Selective cleavage of tert-butyldimethylsilyl, TBDMS, ethers, in the presence of tert-butyldiphenlysilyl, TBDPS, ethers8