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B23096 Ethyltriphenylphosphonium bromide, 98+%

CAS Number
1530-32-1
Synonyms

Stock No. Size Price ($) Quantity Availability
B23096-14 25g 29.10
B23096-22 100g 79.00
B23096-36 500g 284.00
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Ethyltriphenylphosphonium bromide, 98+%

MDL
MFCD00011838
EINECS
216-223-3

Chemical Properties

Formula
C20H20BrP
Formula Weight
371.26
Melting point
206-210°
Flash Point
>200°(392°F)
Storage & Sensitivity
Hygroscopic. Store under Nitrogen. Ambient temperatures.
Solubility
Soluble in methanol. Slightly soluble in water, acetone and isopropanol.

Applications

Ethyltriphenylphosphonium bromide acts as a reactant in the synthesis of D-amino acids from L-cysteine-derived thiazolidines, Leiodolide A through aldol reactions and Horner-Wadsworth-Emmons olefination. It is also used in the preparation of cycloalkanoindolines through diastereoselective intramolecular inimo-ene reactions. Further, it is used as a reagent in solid-state metathesis polycondensation to prepare alkyl-dipropenylthiophene monomers and Mizoroki-Heck cyclization and cascading Tsuji-Trost cyclization reactions.

Notes

Hygroscopic. Incompatible with oxidizing agents.

Literature References

Reaction of the phosphorane (generated using 1 mole of n-BuLi) with an aldehyde at low temperature, followed by a second mole of n-BuLi, gives the -oxido phosphonium ylide which can then be reacted with 1,2-diiodoethane to give (Z)-2-iodo-2-alkenes with high stereoselectivity: J. Chem. Soc., Perkin 1, 1331 (1995). See Appendix 1.

Bagh, F. S. G.; Shahbaz, K.; Mjalli, F. S.; Hashim, M. A.; AlNashef, I. M. Zinc(II) chloride-based deep eutectic solvents for application as electrolytes: Preparation and characterization. J. Mol. Liq. 2015, 204, 76-83.

Harada, K.; Imai, A.; Uto, K.; Carter, R. G.; Kubo, M.; Hioki, H.; Fukuyama, Y. Synthesis of jiadifenin using Mizoroki-Heck and Tsuji-Trost reactions. Tetrahedron 2015, 71 (15), 2199-2209.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H319-H500

Toxic if swallowed. Causes serious eye irritation. May form combustible dust concentrations in air

Precautionary Statements: P264b-P270-P280i-P301+P310-P305+P351+P338-P330-P337+P313-P501c

Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Wear eye/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If eye irritation persists: Get medical advice/attention. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
3599630
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2931.39
TSCA
Yes

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