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Methyl (triphenylphosphoranylidene)acetate

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CAS:2605-67-6
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Methyl (triphenylphosphoranylidene)acetate Basic information
Product Name:Methyl (triphenylphosphoranylidene)acetate
Synonyms:methyl 2-(triphenyl-位鈦?phosphanylidene)acetate;methyl 2-(triphenyl-λ^{5}-phosphanylidene)acetate;methyl 2-(triphenyl-λ5-phosphanylidene)acetate;(TRIPHENYLPHOSPHORANYLIDENE)ACETIC ACID METHYL ESTER;AURORA KA-874;(CARBOMETHOXYMETHYLENE)TRIPHENYLPHOSPHORANE;(METHOXYCARBONYLMETHYLENE)TRIPHENYLPHOSPHORANE;METHYL (TRIPHENYLPHOSPHORANYLIDENE)ACETATE
CAS:2605-67-6
MF:C21H19O2P
MW:334.35
EINECS:220-018-4
Product Categories:Wittig Reagents;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;Wittig Reaction
Mol File:2605-67-6.mol
Methyl (triphenylphosphoranylidene)acetate Structure
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. Refrigerator (+4°C)
form Powder
color White to off-white
Water Solubility insoluble
Sensitive Air Sensitive
BRN 618430
InChIKeyNTNUDYROPUKXNA-UHFFFAOYSA-N
CAS DataBase Reference2605-67-6(CAS DataBase Reference)
EPA Substance Registry SystemAcetic 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 Information
ProviderLanguage
Methyl (triphenylphosphoranylidene)acetate English
ACROS English
SigmaAldrich English
ALFA English
Methyl (triphenylphosphoranylidene)acetate Usage And Synthesis
Chemical Propertieswhite to off-white powder
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.
    Wittig Reaction
Purification MethodsCrystallise 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 Preparation Products And Raw materials
Preparation Productsmethyl 2-(7-hydroxybenzofuran-3-yl)acetate
Tag:Methyl (triphenylphosphoranylidene)acetate(2605-67-6) Related Product Information
N,N-Dimethylformamide Benzyl (triphenylphosphoranylidene)acetate AURORA KA-1179 SPECS AE-848/33625045 ETHYL 4,4,4-TRIFLUORO-2-(TRIPHENYLPHOSPHORANYLIDENE)ACETOACETATE METHYL 2-[5-(4-CHLOROPHENYL)-2-HYDROXY-3-OXO-2,3-DIHYDROFURAN-2-YL]-2-(1,1,1-TRIPHENYL-LAMBDA5-PHOSPHANYLIDENE)ACETATE [CARBETHOXYMETHYLENE] TRIPHENYL PHOSPHORANE [1-14C] METHYL 2-(2-HYDROXY-3-OXO-5-PHENYL-2,3-DIHYDROFURAN-2-YL)-2-(1,1,1-TRIPHENYL-LAMBDA5-PHOSPHANYLIDENE)ACETATE AURORA KA-1073 SALOR-INT L150010-1EA ALLYL OXYCARBONYLMETHYLENE TRIPHENYLPHOSPHORANE Ethyl (triphenylphosphoranylidene)acetate Ethyl 2-(triphenylphosphoranylidene)propionate tert-Butyl(triphenylphosphoranylidene)acetate 2-(TRIPHENYLPHOSPHORANYLIDENE)SUCCINIC ANHYDRIDE AURORA KA-1059 Methyl (triphenylphosphoranylidene)acetate CELLULOSE ACETATE