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5044-52-0 - Vinyltriphenylphosphonium bromide, 97% - Schweizer's Reagent - Triphenylvinylphosphonium bromide - L00708 - Alfa Aesar

L00708 Vinyltriphenylphosphonium bromide, 97%

CAS-Nummer
5044-52-0
Synonyme
Schweizer's Reagent
Triphenylvinylphosphonium bromide

Größe Preis ($) Menge Verfügbarkeit
5g 39,04
25g 77,76
100g 278,40
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Vinyltriphenylphosphonium bromide, 97%

MDL
MFCD00011807
EINECS
225-740-3

Chemische Eigenschaften

Formel
CH2=CHP(C5H5)3Br
Molmasse
369.25
Schmelzpunkt
182-186°
Sensitivität
Light Sensitive & Hygroscopic

Literaturverweise

Conjugate additions of nucleophiles to the double bond give ß-substituted ethyl triphenylphosphonium salts which can be further reacted by Wittig olefination. Sequential reaction with phthalimide and an aldehyde leads, after hydrazinolysis of the resulting N-allylphthalimide, to 3-substituted allylamines: J. Org. Chem., 46, 3119 (1981). N-Alkyl allylamines can also be prepared from alkylamines: Tetrahedron Lett., 24, 3043 (1983):

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A variety of heterocyclic systems can be synthesized by conjugate addition and subsequent Wittig condensation: J. Am. Chem. Soc., 86, 2744, 2963 (1964); J. Org. Chem., 33, 2416 (1968). Use of carbon nucleophiles permits synthesis of carbocyclic systems: J. Org. Chem., 30, 2082 (1965).

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Conjugate addition of organocuprates leads to a new phosphonium salt which can be used in the Wittig olefination. With alkenyl cuprates this provides a stereoselective route to (Z,Z)-1,4-pentadienes: Tetrahedron Lett., 26, 1799 (1985). Sequential reactions, catalyzed by CuBr - Ag2CO3 or CuBr - H2O, with Grignard reagents and Wittig olefination with an aldehyde, have also been reported: J. Org. Chem., 61, 9659 (1996):

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GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Sicherheitshinweise: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
4168860
Harmonized Tariff Code
2931.90
TSCA
No

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