(2-ethoxy-2-oxoethyl)triphenylphosphanium bromide

• ChemBase ID: 74861
• Molecular Formular: C22H22BrO2P
• Molecular Mass: 429.286641
• Monoisotopic Mass: 428.05407857
• SMILES: [P+](c1ccccc1)(c1ccccc1)(c1ccccc1)CC(=O)OCC.[Br-]
• Canonical SMILES: CCOC(=O)C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C22H22O2P.BrH/c1-2-24-22(23)18-25(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21;/h3-17H,2,18H2,1H3;1H/q+1;/p-1
• InChIKey: VJVZPTPOYCJFNI-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-ethoxy-2-oxoethyl)triphenylphosphanium bromide
• IUPAC Traditional name: (2-ethoxy-2-oxoethyl)triphenylphosphanium bromide
• Synonyms: (Ethoxycarbonylmethyl)triphenylphosphonium bromide; (Carboxymethyl)triphenylphosphonium bromide ethyl ester; NSC 60450; (Ethoxycarbonylmethyl)triphenylphosphonium bromide; (Carboethoxymethyl)triphenylphosphonium bromide; Ethyl (triphenylphosphonio)acetate bromide; (2-Ethoxy-2-oxoethyl)triphenylphosphonium bromide; 乙氧甲酰基甲基三苯基溴化膦; (乙氧基羰基甲基)三苯基溴化磷鎓

Database IDs

• CAS Number: 1530-45-6
• EC Number: 216-230-1
• MDL Number: MFCD00011835
• Beilstein Number: 3581273
• PubChem SID: 24865798; 162039779
• PubChem CID: 73731

CALCULATED PROPERTIES

• Acid pKa: 19.34738
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.4009204
• LogD (pH = 7.4): 4.4009204
• Log P: 4.4009204
• Molar Refractivity: 102.9219 cm^3
• Polarizability: 40.63268 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 145-150 °C (dec.)(lit.); ca 150°C dec.

Safety Information

• Storage Warning: Hygroscopic; Irritant
• RTECS: TA2299500
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 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: 98%; 98+%
• Linear Formula: CH3CH2OCOCH2P(C6H5)3Br

DETAILS

Sigma Aldrich - 412252

Packaging
100 g in poly bottle
Application
Reactant for:
• Wittig olefination reactions for synthesis of tetramic acid derivatives1
• Synthesis of precursors for Bergman cyclization2
• Preparation of PPAR agonists derived from thalidomide-related LXR antagonists3
• Synthesis of benzoxaboroles with antimalarial activity4
• Michael acceptor based cysteine protease inhibitors5
• Mechanistic studies of the IspH reductase protein6

REFERENCES

• For reaction with trifluoroacetic anhydride and triethylamine, followed by pyrolysis as a route to perfluoroalkyl acetylenes, see: Org. Synth. Coll., 9, 436 (1998):