2-fluoro-1-methylpyridin-1-ium 4-methylbenzene-1-sulfonate

• ChemBase ID: 97050
• Molecular Formular: C13H14FNO3S
• Molecular Mass: 283.3185632
• Monoisotopic Mass: 283.06784253
• SMILES: [n+]1(c(cccc1)F)C.S(=O)(=O)(c1ccc(cc1)C)[O-]
• Canonical SMILES: Fc1cccc[n+]1C.Cc1ccc(cc1)S(=O)(=O)[O-]
• InChI: InChI=1S/C7H8O3S.C6H7FN/c1-6-2-4-7(5-3-6)11(8,9)10;1-8-5-3-2-4-6(8)7/h2-5H,1H3,(H,8,9,10);2-5H,1H3/q;+1/p-1
• InChIKey: HQWDKLAIDBOLFE-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-fluoro-1-methylpyridin-1-ium 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: 2-fluoro-1-methylpyridin-1-ium tosylate
• Synonyms: 2-Fluoro-1-methylpyridin-1-ium 4-methylbenzenesulfonate; Mukaiyama's reagent; 2-Fluoro-N-methylpyridinium toluene-4-sulphonate 95%; 2-FLUORO-1-METHYLPYRIDINIUM p-TOLUENESULFONATE; 2-Fluoro-1-methylpyridinium p-toluenesulfonate; 2-氟-1-甲基吡啶(盐) 对甲苯磺酸酯; 2-氟-1-甲基吡啶鎓对甲苯磺酸盐

Database IDs

• CAS Number: 58086-67-2
• EC Number: 261-108-3
• MDL Number: MFCD00011983
• Beilstein Number: 4345357
• PubChem SID: 24870698; 24855003; 162083677
• PubChem CID: 171631

CALCULATED PROPERTIES

• Log P: 1.6675739
• Molar Refractivity: 40.6 cm^3
• Polarizability: 16.615282 Å^3
• Polar Surface Area: 57.2 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: -2.1372879
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.7088225
• LogD (pH = 7.4): -0.7088248

PROPERTIES

Physical Property

• Melting Point: 128-131°C; 130-134 °C(lit.); 132-134°C

Safety Information

• Storage Condition: 2-8°C, Desiccate
• Storage Warning: Irritant/Moisture Sensitive; Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥90%; ≥90% (F); 95+%; tech. 90%
• Grade: technical; technical grade
• Impurities: <5% 2-hydroxy-1-methylpyridinium p-toluenesulfonate
• Linear Formula: C6H7FN · C7H7O3S

DETAILS

MP Biomedicals - 02158116

White to yellow powder

Apollo Scientific Ltd - PC3826

Peptide coupling agent. see: Chem.Lett.,547(1984)for synthesis of alpha-ribonucleotides

Sigma Aldrich - 249556

Packaging
5 g in glass bottle

Sigma Aldrich - 47110

Other Notes
Efficient coupling reagent. Review1; Synthesis of thioesters2; Stereoselective synthesis of α-ribonucleotides3

REFERENCES

• Peptide coupling reagent. For peptide reagents, see Appendix 6. Also used in the synthesis of ɑ -ribonucleotides: Chem. Lett., 547 (1984).
• Review of synthetic reactions of onium salts of aza-arenes: Angew. Chem. Int. Ed., 18, 707 (1979).