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52186-89-7 - (1-Ethoxycarbonylcyclopropyl)triphenylphosphonium tetrafluoroborate, 98% - (1-Carboethoxycyclopropyl)triphenylphosphonium tetrafluoroborate - Fuchs' Reagent - A18305 - Alfa Aesar

A18305 (1-Ethoxycarbonylcyclopropyl)triphenylphosphonium tetrafluoroborate, 98%

CAS Number
52186-89-7
Synonyms
(1-Carboethoxycyclopropyl)triphenylphosphonium tetrafluoroborate
Fuchs' Reagent

Size Price ($) Quantity Availability
1g 29.20
5g 118.00
25g 489.00
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(1-Ethoxycarbonylcyclopropyl)triphenylphosphonium tetrafluoroborate, 98%

MDL
MFCD00051879

Chemical Properties

Formula
C24H24BF4O2P
Formula Weight
462.23
Melting point
173-179°
Solubility
Slightly soluble in water.

Applications

(1-Ethoxycarbonylcyclopropyl)triphenylphosphonium tetrafluoroborate is used as pharmaceutical intermediate.

Notes

Stable under recommended storage conditions. Incompatible with oxidizing agents.

Literature References

Seung Won Chung; Mark S.Plummer; Laura A.McAllister; Robert M.OliverIII; Joseph A.Abramite; Yue Shen; Jianmin Sun; Daniel P.Uccello; Joel T.Arcari; Loren M.Price; Justin I.Montgomery. Org. Lett. 2011, 13,(19), 5338-5341.

 

Valuable intermediate for cycloalkenylation of compounds containing a nucleophilic center and a carbonyl group. Nucleophilic ring-opening of the cyclopropyl ring is followed by intramolecular Wittig reaction (see Appendix 1) of the intermediate carbonyl-phosphorane; e.g., with ß-keto esters, cyclopentenes are formed: J. Am. Chem. Soc., 96, 1607 (1974):

With 2-formylcyclohexanones, spirocyclopentenes are obtained: J. Am. Chem. Soc., 99, 7307 (1977). Na carboxylates give 2,3-dihydrofurans: Tetrahedron Lett., 4353 (1975), and thiolcarboxylates give dihydrothiophenes, readily aromatized to thiophenes with DDQ: J. Chem. Soc., Perkin 1, 2403 (1994):

Cyclic imides e.g. Succinimide, A13503, give bridgehead lactams: Liebigs Ann. Chem., 521 (1983); for reaction scheme, see Glutarimide, L00968.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

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

Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
4650673
Harmonized Tariff Code
2931.39
TSCA
No

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