ethyl 2-(triphenyl-λ5-phosphanylidene)propanoate

• ChemBase ID: 68847
• Molecular Formular: C23H23O2P
• Molecular Mass: 362.401281
• Monoisotopic Mass: 362.14356661
• SMILES: C(=O)(C(=P(c1ccccc1)(c1ccccc1)c1ccccc1)C)OCC
• Canonical SMILES: CCOC(=O)C(=P(c1ccccc1)(c1ccccc1)c1ccccc1)C
• InChI: InChI=1S/C23H23O2P/c1-3-25-23(24)19(2)26(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22/h4-18H,3H2,1-2H3
• InChIKey: KZENFXVDPUMQOE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-(triphenyl-λ^5-phosphanylidene)propanoate; ethyl 2-(triphenyl-$l^{5}-phosphanylidene)propanoate
• IUPAC Traditional name: ethyl 2-(triphenyl-λ^5-phosphanylidene)propanoate; ethyl 2-(triphenyl-$l^{5}-phosphanylidene)propanoate
• Synonyms: Ethyl 2-(triphenylphosphoranylidene)propionate; (Carbethoxyethylidene)triphenylphosphorane; Ethyl 2-(triphenyl-lambda5-phosphanylidene)propanoate; (Ethoxycarbonylethylidene)triphenylphosphorane; Ethyl 2-(triphenylphosphoranylidene)propanoate; (1-Carboethoxyethylidene)triphenylphosphorane; (1-Ethoxycarbonylethylidene)triphenylphosphorane; 乙氧甲酰亚乙基三苯基膦; 乙氧甲酰基亚乙基三苯基膦; (1-乙氧基羰基乙基亚乙基)三苯基磷烷

Database IDs

• CAS Number: 5717-37-3
• EC Number: 227-215-4
• MDL Number: MFCD00009160
• Beilstein Number: 757112
• PubChem SID: 162034577; 24863517
• PubChem CID: 79792

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 6.8384
• LogD (pH = 7.4): 6.8384
• Log P: 6.8384
• Molar Refractivity: 107.6874 cm^3
• Polarizability: 42.46232 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 154-160°C; 158-162 °C(lit.)

Safety Information

• Storage Warning: Air Sensitive; IRRITANT; Irritant
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 94%; 95+%; 97%
• Grade: technical grade
• Linear Formula: CH3C[=P(C6H5)3]CO2C2H5

DETAILS

Sigma Aldrich - 377708

Other Notes
Contains triphenylphosphine oxide
Packaging
5, 25 g in glass bottle

REFERENCES

• Stable ylide which reacts with aldehydes to give ?-substituted methacrylic esters. See Appendix 1.
• With acyl halides, gives allenic esters: Helv. Chim. Acta, 63, 438 (1980); Org. Synth. Coll., 7, 232 (1990):
  
• Reacts with the carbonyl group of succinic anhydride giving an intermediate useful in the synthesis of 2,2-dialkylcyclopentane-1,3-diones: Synthesis, 845 (1986):