(2-oxoethyl)triphenylphosphanium chloride

• ChemBase ID: 152270
• Molecular Formular: C20H18ClOP
• Molecular Mass: 340.783081
• Monoisotopic Mass: 340.07837951
• SMILES: c1ccc(cc1)[P+](CC=O)(c1ccccc1)c1ccccc1.[Cl-]
• Canonical SMILES: O=CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Cl-]
• InChI: InChI=1S/C20H18OP.ClH/c21-16-17-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20;/h1-16H,17H2;1H/q+1;/p-1
• InChIKey: RVEJRPJGKXTQIF-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-oxoethyl)triphenylphosphanium chloride
• IUPAC Traditional name: (2-oxoethyl)triphenylphosphanium chloride
• Synonyms: 2-Oxoethyltriphenylphosphonium chloride; (Formylmethyl)triphenylphosphonium chloride; 2-Oxoethyltriphenylphosphomium chloride; (Formylmethyl)triphenylphosphonium chloride; 2-氧乙基三苯基氯化磷; (甲酰甲基)三苯基氯化磷; (甲酰基甲基)三苯基氯化鏻

Database IDs

• CAS Number: 62942-43-2
• EC Number: 263-767-2
• MDL Number: MFCD00012003
• Beilstein Number: 4060813
• PubChem SID: 24871339; 162246415
• PubChem CID: 2733863

CALCULATED PROPERTIES

• Acid pKa: 18.874743
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.739602
• LogD (pH = 7.4): 3.739602
• Log P: 3.739602
• Molar Refractivity: 92.4788 cm^3
• Polarizability: 36.28601 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 209-212 °C (dec.)(lit.); ca 210°C dec.

Safety Information

• Storage Warning: Hygroscopic
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-41
• Safety Statements: 26-36/37/39; 26-39
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H318; H302-H318
• GHS Precautionary statements: P280-P301+P310-P305+P351+P338-P321-P405-P501A; P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (AT); 97%; 98%; 98+%
• Linear Formula: HCOCH2P(Cl)(C6H5)3

DETAILS

Sigma Aldrich - 47718

Packaging
10 g in glass bottle
Application
Reactant for:
• Hydroazidation reactions in preparation of a-azido alcohols1
• Preparation of prodrug (2-hydroxyamino-vinyl)-triphenyl-phosphonium (HVTP) inhibitor of peroxidase activity and apoptosis2
• Intramolecular [4 + 3] cycloaddition reactions3

REFERENCES

• Undergoes the Wittig reaction with aldehydes to give acrylic aldehydes either in the presence of base or by prior conversion to the phosphorane. For references see (Formylmethylene)triphenylphosphorane, A11709.