CAS 2605-67-6 Methyl (triphenylphosphoranylidene)acetate

Synonyms

1-(Triphenylphosphonio)-2-oxo-2-methoxyethan-1-ide; methyl(triphenylphosphoranylideneacetate); RTR-011791; NCGC00161084-02; (methoxycarbonylmethylene) triphenylphosphorane; triphenyl phosphanyliden-acetic acid methyl ester; (Carbomethoxymethylene)triphenylphosphorane; NSC-117573; Methyl (triphenyphosphoranylidene)acetate; ST2413263;

IUPAC Name

methyl 2-(triphenyl-λ5-phosphanylidene)acetate;

Molecular Weight

334.355g/mol

Molecular Formula

C21H19O2P;

Canonical SMILES

COC(=O)C=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3;

InChI

InChI=1S/C21H19O2P/c1-23-21(22)17-24(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17H,1H3;

InChI Key

NTNUDYROPUKXNA-UHFFFAOYSA-N;

Storage

Refrigerator (+4°C)

Complexity

400

Covalently-Bonded Unit Count

EC Number

220-018-4

Exact Mass

334.112g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

334.112g/mol

NSC Number

407395

Rotatable Bond Count

Topological Polar Surface Area

26.3A^2

Application

Methyl (triphenylphosphoranylidene)acetate, a white to off-white powder, serves a crucial role as a Wittig reagent in organic chemistry. It is commonly used in olefination reactions, where it facilitates the two-carbon homologation of aldehydes to yield α,β-unsaturated esters. By undergoing the Wittig reaction with aldehydes, it produces substituted methyl acrylates, making it invaluable for the synthesis of various organic compounds. This reagent is also instrumental in efficiently synthesizing pyrazoles through its reaction with methyl diazoacetate in the presence of triethylamine. Additionally, it finds application in preparing (triphenylphosphoranylidene)-ketene. An illustrative example of its use is the reaction with 2-nitrobenzaldehyde, which results in methyl (2E)-3-(2-nitrophenyl) acrylate and a triphenylphosphine oxide side product, demonstrating its effectiveness in a silica gel matrix for optimal product dispersion during chromatography.

January 15, 2025

Methyl (triphenylphosphoranylidene)acetate: A Powerful Tool for Organic Synthesis

This reagent proved invaluable in my research, facilitating the Wittig reaction to convert aldehydes to α,β-unsaturated esters efficiently. It performed well in synthesizing pyrazoles, enhancing our lab's productivity significantly.