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2091-46-5 - Propargyltriphenylphosphonium bromide, 97% - Triphenylpropargylphosphonium bromide - Triphenyl-2-propyn-1-ylphosphonium bromide - A12753 - Alfa Aesar

A12753 Propargyltriphenylphosphonium bromide, 97%

Codice CAS
2091-46-5
Sinonimi
Triphenylpropargylphosphonium bromide
Triphenyl-2-propyn-1-ylphosphonium bromide

Dimensioni Prezzo ($) Quantità Disponibilità
5g 36,67
25g 128,75
100g 387,28
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Propargyltriphenylphosphonium bromide, 97%

MDL
MFCD00011811
EINECS
218-242-2

Proprietà chimiche

Formula
C21H18BrP
Peso formula
381.26
Punto di fusione
177-182°
Sensibilità
Hygroscopic
Solubilità
Soluble in methanol.

Applicazioni

Propargyltriphenylphosphonium bromide can be used in the alcylation of amines. It is a commonly used as a Wittig reagent.

Note

Hygroscopic. Store in cool dry place in tightly closed container. With good ventilation. Store away from oxidizing agent and water/moisture.

Letteratura

M.H. Wahdan; A.A. Hermas; M.S. Morad. Corrosion inhibition of carbon-steels by propargyltriphenylphosphonium bromide in H2SO4 solution. Materials Chemistry and Physics. 2002, 76(2), 111-118.

Yeong-Soon Gal. A Facile Synthetic Method of Poly(Propargyltriphenylphosphonium-Tetraphenylborate) Via Ion Exchange Reaction of Poly(Propargyltriphenylphosphonium Bromide) Using Tetraphenylboron Sodium. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry. 1995, 321031-1038.

Precursor of enynes by the Wittig reaction: Liebigs Ann. Chem., 682, 62 (1965); J. Org. Chem., 42, 200 (1977); see Appendix 1.

Readily undergoes additions with nucleophiles, e.g. alcohols or amines, to give 2-alkoxy or 2-alkylamino propenyl phosphonium salts. In these reactions, the reactive species is the allenic isomer, propadienyl triphenylphosphonium bromide: J. Org. Chem., 42, 200 (1977). By using a chiral alcohol, the subsequent base-promoted Wittig reaction with carbonyl compounds yields amino or alkoxy dienes which undergo face-selective Diels-Alder additions to dienophiles: J. Chem. Soc., Chem. Commun., 1785 (1995):

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H302-H315-H319-H335

Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Dichiarazioni precauzionali: P280h-P305+P351+P338

Wear protective gloves/clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Altri riferimenti

Beilstein
3579775
Codice tariffe armonizzato
2931.90
TSCA
No

Raccomandato

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    Triethylene glycol, 99%
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    (Methoxymethyl)triphenylphosphonium chloride, 98+%
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    (Methoxycarbonylmethyl)triphenylphosphonium bromide, 98+%
  • A18241

    p-Xylylenebis(triphenylphosphonium bromide), 96%
  • H27798

    1,3-Diisopropylimidazolium chloride, 97+%

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