CAS 1530-32-1|ethyltriphenylphosphanium bromide|ethyltriphenylphosphanium bromide|Ethyl(trisphenyl)phosphonium bromide|乙基三苯基溴化膦|TEP|Ethyltriphenylphosphonium bromide|Ethyltriphenylphosphoniu...

General Information

Structure

Molecular Formula

C₂₀H₂₀BrP

Molecular Mass

371.250561

Exact Mass

370.04859927

Charge

InChI

InChI=1S/C20H20P.BrH/c1-2-21(18-12-6-3-7-13-18,19-14-8-4-9-15-19)20-16-10-5-11-17-20;/h3-17H,2H2,1H3;1H/q+1;/p-1

InChIKey

JHYNXXDQQHTCHJ-UHFFFAOYSA-M

Canonic Smiles

CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]

Isomeric Smiles

[P+](c1ccccc1)(c1ccccc1)(c1ccccc1)CC.[Br-]

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

4.984599

LogD (pH = 7.4)

4.984599

Log P

4.984599

Molar Refractivity

91.9698

Polarizability

36.28101

Polar Surface Area

0.0

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

ethyltriphenylphosphanium bromide

IUPAC name

ethyltriphenylphosphanium bromide

Synonyms

Ethyl(trisphenyl)phosphonium bromide乙基三苯基溴化膦TEPEthyltriphenylphosphonium bromideEthyltriphenylphosphonium BromideTriphenylethylphosphonium BromideTEP (onium compound)乙基三苯基溴化磷

Names and Identifiers

Registration numbers

PubChem CID

73727

PubChem SID

1620414532484565324894599

EC Number

Beilstein Number

CAS Number

MDL Number

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

E50604

Packaging
25, 100 g in poly bottle
Application
Reactant for synthesis of:
• D-amino acids from L-cysteine-derived thiazolidines1
• Leiodolide A via aldol reactions and Horner-Wadsworth-Emmons olefination2
• Cycloalkanoindolines via diastereoselective intramolecular inimo-ene reactions3
• WXYZA′ domain of maitotoxin using the coupling of key building blocks4Reactant for:
• Solid-state metathesis polycondensation to form alkyl-dipropenylthiophene monomers5
• Mizoroki-Heck cyclization and cascading Tsuji-Trost cyclization / lactonization cyclization reactions for synthesis of an ABC ring system6

04997

Application
Reactant for synthesis of:
• D-amino acids from L-cysteine-derived thiazolidines1
• Leiodolide A via aldol reactions and Horner-Wadsworth-Emmons olefination2
• Cycloalkanoindolines via diastereoselective intramolecular inimo-ene reactions3
• WXYZA′ domain of maitotoxin using the coupling of key building blocks4Reactant for:
• Solid-state metathesis polycondensation to form alkyl-dipropenylthiophene monomers5
• Mizoroki-Heck cyclization and cascading Tsuji-Trost cyclization / lactonization cyclization reactions for synthesis of an ABC ring system6

TRC

E931950

Ethyltriphenylphosphonium Bromide is used as a wittig reagent. Ethyltriphenylphosphonium Bromide and other phosphonium salts show antiviral activity.

Molecule Details

References

PubChem Literature

From Data Sources

• Romanov, G.V. et al.: Khim.-Farm. Zhur., 24, 28 (1990)

• 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.

References

Bioactivity

PubChem BioAssay

Bioactivity