Methyl (triphenylphosphoranylidene)acetate

Catalog Number

ACM2605676

Product Name

Methyl (triphenylphosphoranylidene)acetate

Structure

CAS

2605-67-6

Category

Heterocyclic Organic Compound

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;

Application

(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.

used in an efficient synthesis of pyrazoles via reaction with methyl diazoacetate in the presence of triethylamine.

It is used in the preparation of (triphenylphosphoranylidene)-ketene.

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.

Storage

Refrigerator (+4°C)

Complexity

400

Covalently-Bonded Unit Count

1

EC Number

220-018-4

Exact Mass

334.112g/mol

H-Bond Acceptor

2

Heavy Atom Count

24

Monoisotopic Mass

334.112g/mol

NSC Number

407395

Rotatable Bond Count

5

Topological Polar Surface Area

26.3A^2

MSDS

COA

Spec Sheet