Methyl (triphenylphosphoranylidene)acetate Chemical Properties

Melting point:

168-172 °C (lit.)

Boiling point:

165～170℃

Density 

1.17±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Acetonitrile (Slightly), Chloroform (Slightly)

form 

Powder

color 

White to off-white

Water Solubility 

insoluble

Sensitive 

Air Sensitive

BRN 

618430

InChIKey

NTNUDYROPUKXNA-UHFFFAOYSA-N

CAS DataBase Reference

2605-67-6(CAS DataBase Reference)

EPA Substance Registry System

Acetic acid, (triphenylphosphoranylidene)-, methyl ester (2605-67-6)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

36/37/38-25

Safety Statements 

22-24/25-36-26

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29319090

MSDS

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Methyl (triphenylphosphoranylidene)acetate Usage And Synthesis

Chemical Properties

white to off-white powder

Uses

(Methoxycarbonylmethylene)triphenylphosphorane is used in olefination reactions. Further, it undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates. It is used in the preparation of (triphenylphosphoranylidene)-ketene.

Uses

Wittig reagent for the two-carbon homologation of aldehydes to α,β-unsaturated esters. Also used in an efficient synthesis of pyrazoles via reaction with methyl diazoacetate in the presence of triethylamine.

Uses

1. (Methoxycarbonylmethylene)triphenylphosphorane is used in olefination reactions. Wittig reagent for the two-carbon homologation of aldehydes to α,β-unsaturated esters. it undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates.
2. used in an efficient synthesis of pyrazoles via reaction with methyl diazoacetate in the presence of triethylamine.
3. It is used in the preparation of (triphenylphosphoranylidene)-ketene.
4. The Wittig reaction we performed in class involved the reaction of 2-nitrobenzaldehyde (1) with methyl (triphenylphosphoranylidene) acetate (2) to produce methyl (2E)-3-(2-nitrophenyl) acrylate (3) with a triphenylphosphine oxide (4) side product, and took place in a silica gel matrix to ensure even product dispersion for chromatography.
   

Purification Methods

Crystallise it by dissolving in it AcOH and adding pet ether (b 40-50o) to give colourless plates. UV max (A 1mm ): 222nm (865) and 268nm (116) [Isler et al. Helv Chim Acta 40 1242 1957]. [Beilstein 16 IV 977.]

Methyl (triphenylphosphoranylidene)acetate(2605-67-6)Related Product Information

• Cellulose acetate
• Ammonium acetate
• N,N-Dimethylformamide
• Magnesium acetate
• Vinyl acetate
• Triphenylphosphine
• Sodium acetate
• Benzyl acetate
• Tris(triphenylphosphine)rhodiu
• Butyl acetate
• Methyl acetate
• Ethyl acetate
• (Carbomethoxymethyl)triphenylphosphonium bromide
• (Z)-2-Methoxyimino-2-(furyl-2-yl) acetic acid ammonium salt
• DIMETHYL METHOXYMETHYLENEMALONATE
• isopropyl 2-Methoxyacetate
• Methyl
• ACETATE