Benzyl (triphenylphosphoranylidene)acetate Chemical Properties

Melting point:

120-122 °C(lit.)

Boiling point:

571.1±43.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Powder

color 

White to off-white

InChI

InChI=1S/C27H23O2P/c28-27(29-21-23-13-5-1-6-14-23)22-30(24-15-7-2-8-16-24,25-17-9-3-10-18-25)26-19-11-4-12-20-26/h1-20,22H,21H2

InChIKey

INKMLGJBBDRIQR-UHFFFAOYSA-N

SMILES

C(OCC1=CC=CC=C1)(=O)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

36/37/39-26-22-24/25

WGK Germany 

3

HS Code 

29319019

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Benzyl (triphenylphosphoranylidene)acetate Usage And Synthesis

Chemical Properties

white to off-white powder

Uses

Reactant for:

• Tributylphosphine-mediated vinylogous Wittig reactions
• Synthesis of 1,2-dioxanes for antitrypanosomal activity
• Organocatalytic Michael-type reactions / Wittig reactions of phosphorus ylides and unsaturated ketones
• Stereoselective phosphine-catalyzed cycloaddition to form spirocyclopenteneoxindoles
• Enantioselective synthesis of pantothenic acid
• Preparation of phosphorus ylides from phosphoranes and acetic anhydride

reaction suitability

reaction type: C-C Bond Formation

Synthesis

The general procedure for the synthesis of (benzyloxycarbonylmethylene)triphenylphosphonium bromide from benzyloxycarbonylmethylene)triphenylphosphonium bromide was as follows: (2-(benzyloxy)-2-oxoethyl)triphenylphosphonium bromide (2.00 g, 4.07 mmol) and NaOH (0.081 g, 2.035 mmol) were dissolved in CH2Cl2 (20 mL), and the reaction was stirred for 1 hr at 25 °C . After completion of the reaction, the reaction mixture was diluted with CH2Cl2 (50 mL) and washed with deionized water (30 mL). The organic layer was separated and concentrated to afford benzyl 2-(triphenylphosphoranylidene)acetate (1.5 g, 3.25 mmol, 80% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.60-7.65 (m, 6H), 7.51-7.54 (m, 4H), 7.42-7.46 (m, 6H), 7.20 (s, 4H), 5.00 (s, 2H), 2.96 (s, 1H); LC-MS(ESI) m/z 411.1 (M + H) +.

References

[1] Heterocycles, 2007, vol. 73, # C, p. 751 - 768
[2] Patent: US2018/99931, 2018, A1. Location in patent: Paragraph 2180
[3] Organic Letters, 2005, vol. 7, # 19, p. 4289 - 4291
[4] Patent: WO2006/17542, 2006, A1. Location in patent: Page/Page column 42-43
[5] Chemistry - A European Journal, 2009, vol. 15, # 47, p. 12926 - 12928

Benzyl (triphenylphosphoranylidene)acetate(15097-38-8)Related Product Information

• Vinyl acetate
• Isopropyl-α-[2-methylhydrazino]-p-toluamide
• Benzyl chloride
• Benzyl isocyanate
• Triphenylphosphine
• Benzyl benzoate
• Benzyl alcohol
• Benzyl nicotinate
• Bis(triphenylphosphine)palladium(II) chloride
• 4-Trifluoromethylbenzyl chloride
• Ethyl acetate
• 2-Methylbenzyl chloride
• Sodium acetate
• Tris(triphenylphosphine)chlororhodium
• ACETATE
• Benzyl
• Methyl (triphenylphosphoranylidene)acetate
• Ethyl (triphenylphosphoranylidene)acetate