ethyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate

• ChemBase ID: 69791
• Molecular Formular: C22H21O2P
• Molecular Mass: 348.374701
• Monoisotopic Mass: 348.12791654
• SMILES: P(=CC(=O)OCC)(c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C22H21O2P/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/h3-18H,2H2,1H3
• InChIKey: IIHPVYJPDKJYOU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate; ethyl 2-(triphenyl-λ^5-phosphanylidene)acetate
• IUPAC Traditional name: ethyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate; ethyl 2-(triphenyl-λ^5-phosphanylidene)acetate
• Synonyms: (Ethoxycarbonylmethylene)triphenylphosphorane; (Carbethoxymethylene)triphenylphosphorane; Ethyl (triphenylphosphoranyliden)acetate; Ethyl (triphenylphosphoranylidene)acetate; (Ethoxycarbonylmethylene)triphenylphosphorane; 2-(Triphenylphosphoranylidene)acetic Acid Ethyl Ester; (2-Ethoxy-2-oxoethylidene)triphenylphosphorane; NSC 72406; (Carbethoxymethylene)triphenylphosphorane; (2-Ethoxy-2-oxoethylidene)triphenylphosphorane; (Carbethoxymethylene)triphenylphosphorane; (Carbethoxymethylidene)triphenylphosphorane; (Ethoxycarbonylmethylidene)triphenylphosphorane; Ethyl (triphenylphosphoranylidene)acetate; Triphenylcarbethoxymethylenephosphorane; (Carboethoxymethylene)triphenylphosphorane; (Ethoxycarbonylmethylene)triphenylphosphorane; ethyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate; (乙氧基羰基亚甲基)三苯基磷烷; 乙基(三苯基膦)乙酸酯; 乙氧甲酰基亚甲基三苯基膦; 乙基(三苯基膦)乙酸酯; (乙氧基羰基亚甲基)三苯基磷烷

Database IDs

• CAS Number: 1099-45-2
• EC Number: 214-151-7
• MDL Number: MFCD00009183
• Beilstein Number: 754639
• PubChem SID: 24845336; 162035516; 24892754
• PubChem CID: 24892754; 70670
• Chemspider ID: 63836
• Wikipedia Title: Triphenylcarbethoxymethylenephosphorane

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 6.2381
• LogD (pH = 7.4): 6.2381
• Log P: 6.2381
• Molar Refractivity: 103.1977 cm^3
• Polarizability: 40.616707 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid
• Melting Point: 124-129 °C; 125-127°C; 126-130°C; 128 - 130°C; 128-130 °C(lit.); 128-130°C; 128-131 °C
• Hydrophobicity(logP): 6.662

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Air Sensitive; IRRITANT; Irritant/Air Sensitive/Moisture Sensitive/Store under Argon/Keep Cold
• German water hazard class: 3
• TSCA Listed: false; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90%; 95%; 95+%; 98%; 98+%
• Grade: technical
• Linear Formula: (C6H5)3P=CHCO2CH2CH3; (C6H5)3P=CHCOOCH2CH3

DETAILS

Sigma Aldrich - C5106

Packaging
25, 100 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 02595

Application
Stabilized phosphoran

Toronto Research Chemicals - C175910

A common Wittig reagent. A cholinesterase inhibitor.

REFERENCES

• Naito, T., et al.: Chem. Pharm. Bull., 44, 624 (1996)
• Hata, A., et al.: Mol. Pharmacol., 67, 640 (1996)
• Stable crystalline ylide which reacts with aldehydes giving substituted ethyl acrylates. This reaction has been used in an indole synthesis from o-nitrobenzaldehydes: Synthesis, 862 (1984); 401 (1987):
  
• More highly-substituted ylides can be prepared by alkylation (e.g. with benzyl bromide) and abstraction of a proton by NaOH. See, e.g.: Synth. Commun., 19, 1899 (1989).
• Reaction with acid chlorides leads to esters of allenic acids. See, e.g.: Org. Synth. Coll., 7, 232 (1990).
• See also (Methoxycarbonylmethylene)triphenylphosphorane, A14020, and Appendix 1.
• Coumarins have been synthesized from o-hydroxy acetophenones: Monatsh. Chem., 115, 765 (1984); o-hydroxy aldehydes give the 4-unsubstituted analogues: Chem. Pharm. Bull., 39, 3100 (1991); 42, 2032 (1994); Indian J. Chem. B, 32, 1159 (1993):