ethyltriphenylphosphanium bromide

• ChemBase ID: 76549
• Molecular Formular: C20H20BrP
• Molecular Mass: 371.250561
• Monoisotopic Mass: 370.04859927
• SMILES: [P+](c1ccccc1)(c1ccccc1)(c1ccccc1)CC.[Br-]
• Canonical SMILES: CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyltriphenylphosphanium bromide
• IUPAC Traditional name: ethyltriphenylphosphanium bromide
• Synonyms: TEP (onium compound); Triphenylethylphosphonium Bromide; Ethyltriphenylphosphonium Bromide; TEP; Ethyltriphenylphosphonium bromide; Ethyl(trisphenyl)phosphonium bromide; 乙基三苯基溴化膦; 乙基三苯基溴化磷

Database IDs

• CAS Number: 1530-32-1
• EC Number: 216-223-3
• MDL Number: MFCD00011838
• Beilstein Number: 3599630
• PubChem SID: 162041453; 24894599; 24845653
• PubChem CID: 73727

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.984599
• LogD (pH = 7.4): 4.984599
• Log P: 4.984599
• Molar Refractivity: 91.9698 cm^3
• Polarizability: 36.28101 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: ~205 °C; 203-205 °C(lit.); 203-205°C; 206-210°C; 208-210°C
• Flash Point: >200 °C; >200°C; >200°C(392°F); >392 °F

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Hygroscopic; Toxic/Harmful/Hygroscopic/Store under Argon
• European Hazard Symbols: Nature polluting (N); X; Harmful (Xn)
• UN Number: 3077; UN3077
• German water hazard class: 2
• Hazard Class: 9
• Packing Group: 3; III
• Risk Statements: 21/22-36/37/38-51/53; 22-51/53
• Safety Statements: 26-36/37-61; 61
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H411; H302-H312-H315-H319-H335-H411-H401
• GHS Precautionary statements: P273-P301 + P310; P280H-P273-P305+P351+P338-P309-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3077 9/PG 3

Product Information

• Purity: ≥98.5% (AT); 98%; 98+%; 99%
• Grade: purum
• Linear Formula: [(C6H5)3P+C2H5]Br-

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

Sigma Aldrich - 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

Toronto Research Chemicals - E931950

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

REFERENCES

• 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.