sodium 4-methylbenzene-1-sulfinate

• ChemBase ID: 295202
• Molecular Formular: C7H7NaO2S
• Molecular Mass: 178.18405
• Monoisotopic Mass: 178.00644475
• SMILES: Cc1ccc(cc1)S(=O)O[Na]
• Canonical SMILES: [Na]OS(=O)c1ccc(cc1)C
• InChI: InChI=1S/C7H8O2S.Na/c1-6-2-4-7(5-3-6)10(8)9;/h2-5H,1H3,(H,8,9);/q;+1/p-1
• InChIKey: KFZUDNZQQCWGKF-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 4-methylbenzene-1-sulfinate
• IUPAC Traditional name: sodium 4-methylbenzenesulfinate
• Synonyms: Sodium p-toluenesulfinate; 4-Methylbenzenesulfinic acid sodium salt; p-Toluenesulfinic acid sodium salt; 对甲苯亚磺酸钠

Database IDs

• CAS Number: 824-79-3
• EC Number: 212-538-5
• MDL Number: MFCD00149640
• Beilstein Number: 4621454
• PubChem SID: 180680733
• PubChem CID: 2723791

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.0184
• LogD (pH = 7.4): 2.0184
• Log P: 2.0184
• Molar Refractivity: 41.0309 cm^3
• Polarizability: 18.03011 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300°C

Safety Information

• Storage Warning: Hygroscopic
• RTECS: XT4725000
• TSCA Listed: 是

Product Information

• Purity: 97% (dry wt.), water <5%

REFERENCES

• In the presence of CuI, iodoarenes undergo displacement in DMF to give moderate to good yields of diaryl sulfones: Tetrahedron Lett., 36, 6239 (1995).
• Alkylation with reactive halides leads to alkyl sulfones. Alkylation of sulfinates can be carried out in a polyethylene glycol as solvent/catalyst: Bull. Chem. Soc. Jpn., 57, 613 (1984). Reaction with allylic alcohols also gives sulfones: J. Org. Chem., 55, 3274 (1990). For asymmetric sulfonylation of allylic chlorides, catalyzed by a chiral Pd complex, see: Tetrahedron: Asymmetry, 6, 643 (1995).
• For use as a precursor of p-toluenesulfonyldiazomethane, via Mannich reaction with formaldehyde and urethane, nitrosation and cleavage with alumina, see: Org. Synth. Coll.,6, 981 (1988):
  
• Also undergoes free-radical reactions in the presence of Cu(II), activated either thermally or by sonication. For example, addition-cyclization of 5-heteroarylpent-1-enes: Synlett, 763 (1995):