(methoxymethyl)triphenylphosphanium chloride

• ChemBase ID: 74876
• Molecular Formular: C20H20ClOP
• Molecular Mass: 342.798961
• Monoisotopic Mass: 342.09402957
• SMILES: [P+](c1ccccc1)(c1ccccc1)(c1ccccc1)COC.[Cl-]
• Canonical SMILES: COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Cl-]
• InChI: InChI=1S/C20H20OP.ClH/c1-21-17-22(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20;/h2-16H,17H2,1H3;1H/q+1;/p-1
• InChIKey: SJFNDMHZXCUXSA-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (methoxymethyl)triphenylphosphanium chloride
• IUPAC Traditional name: (methoxymethyl)triphenylphosphanium chloride
• Synonyms: (Methoxymethyl)tris(phenyl)phosphonium chloride; (Methoxymethyl)triphenylphosphonium chloride; (Methoxymethyl)triphenylphosphonium chloride; (甲氧基甲基)三苯基氯化膦; (甲氧基甲基)三苯基氯化磷鎓

Database IDs

• CAS Number: 4009-98-7
• EC Number: 223-664-5
• MDL Number: MFCD00011800
• Beilstein Number: 3599844; 924215
• PubChem SID: 162039794; 24858739; 24883807
• PubChem CID: 2723798

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.3299503
• LogD (pH = 7.4): 4.3299503
• Log P: 4.3299503
• Molar Refractivity: 93.3594 cm^3
• Polarizability: 36.911068 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 185-195 °C (dec.)(lit.); 185-195(dec.)°C; ca 190°C dec.

Safety Information

• Storage Warning: Harmful/Irritant/Hygroscopic/Store under Argon; Hygroscopic
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335; H302-H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (AT); 97%; 98%; 98+%
• Grade: purum
• Impurities: ≤1% water
• Linear Formula: (C6H5)3P(Cl)CH2OCH3

DETAILS

Sigma Aldrich - 309567

Packaging
25, 100 g in glass bottle

Sigma Aldrich - 65120

Other Notes
Convenient precursor to the Wittig-reagent for the methoxymethylenation of carbonyl compounds1; Used e.g. in the synthesis of steroids2,3; Sesquiterpenoids4; Prostaglandin analogs5

REFERENCES

• Wittig reaction (see Appendix 1) of the derived phosphorane with aldehydes and ketones gives enol ethers, readily hydrolyzed to homologous aldehydes. For an example (adamantanone to adamantanecarboxaldehyde), see: Chem. Ber., 95, 2514 (1962). For use of the reaction in the synthesis of hydroisoquinoline AMPA antagonists, see: J. Med. Chem., 39, 2219 (1996). Reaction with chiral 2,3-epoxyaldehydes provides an enantioselective synthesis of (E)-4-hydroxyalkenes: J. Chem. Soc., Chem. Commun., 232 (1993).