| Identification | More | [Name]
Ethyltriphenylphosphonium bromide | [CAS]
1530-32-1 | [Synonyms]
ETHYLTRIPHENYLPHOSPHONIUM BROMIDE
ETPPBR
TEP
TRIPHENYLETHYLPHOSPHONIUM BROMIDE
Ethyltriphenylbromophosphine
ethyltriphenyl-phosphoniubromide
ETHYLTRIPHENYLPHOSPHONIUM BRIMIDE
ethyl triphenylphosphoiuum bromide
ETHYLTRIPHENYLPHOSPHONIUM BROMIDE 99+%
Phosphonium, ethyltriphenyl-, bromide
ETPPBr: Ethyltriphenylphosphonium Bromide
ETHYL TRIPHENYL PHOSPHENIUM BROMID
Ethyl triphenylphosphonium Bromide(ETPPBr)
Ethyltriphenylphosphonium bromide, 98+%
ETHYLTRIPHENYLPHOSPHONIUM BROMIDE pure | [EINECS(EC#)]
216-223-3 | [Molecular Formula]
C20H20BrP | [MDL Number]
MFCD00011838 | [Molecular Weight]
371.25 | [MOL File]
1530-32-1.mol |
| Chemical Properties | Back Directory | [Appearance]
White to off-white crystalline powder | [Melting point ]
203-205 °C(lit.)
| [Boiling point ]
240℃[at 101 325 Pa] | [density ]
1.38[at 20℃] | [vapor pressure ]
0-0.1Pa at 20-25℃ | [Fp ]
200 °C | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
174g/l soluble | [form ]
Crystalline Powder | [color ]
White to off-white | [Water Solubility ]
120 g/L (23 ºC) | [Sensitive ]
Hygroscopic | [BRN ]
3599630 | [InChIKey]
JHYNXXDQQHTCHJ-UHFFFAOYSA-M | [LogP]
-0.69--0.446 at 35℃ | [CAS DataBase Reference]
1530-32-1(CAS DataBase Reference) | [Storage Precautions]
Moisture sensitive | [EPA Substance Registry System]
1530-32-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R36/37/38:Irritating to eyes, respiratory system and skin .
R21/22:Harmful in contact with skin and if swallowed . | [Safety Statements ]
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 3077 9/PG 3
| [WGK Germany ]
2
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29310095 |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white crystalline powder | [Flammability and Explosibility]
Notclassified | [reaction suitability]
reaction type: C-C Bond Formation | [Synthesis]
In a 1500 mL three-necked flask, 54 g (0.5 mol) of ethyl bromide, 210 g (0.8 mol) of triphenylphosphine and 1000 mL of toluene were added sequentially. A reflux condenser tube was installed, magnetic stirring was turned on and the reaction was heated to reflux state and kept at reflux for 10 hours. Upon completion of the reaction, the reaction system was naturally cooled to 50 °C and a large amount of white solid was observed to precipitate. The solid product was collected by filtration through a Brinell funnel and the filter cake was washed with toluene three times (50 mL each time). The resulting solid was transferred to a vacuum drying oven and dried at 50 °C until constant weight, resulting in 170.4 g of ethyltriphenylphosphonium bromide in 91.8% yield. | [Purification Methods]
Recrystallise it from H2O and dry it in high vacuum at 100o. IR has bands at 1449, 1431 and 997cm-1 . [Wittig & Wittenberg Justus Liebigs Ann Chem 606 1 1957, Bergmann & Dusza J Org Chem 23 1245 1958, Beilstein 16 IV 982.] | [References]
[1] Journal of Fluorine Chemistry, 2002, vol. 113, # 2, p. 177 - 183
[2] Pharmazie, 1999, vol. 54, # 1, p. 26 - 30
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1989, vol. <2> 38, # 12, p. 2553 - 2556
[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, vol. <2> 38, # 12, p. 2789 - 2792
[5] Journal of the American Chemical Society, 1980, vol. 102, p. 2437 |
| Questions and Answers (Q&A) | Back Directory | [Uses]
Ethyltriphenylphosphonium Bromide (ETPB) is a phase transfer catalyst, used to accelerate the cure of phenolic-based epoxy resins, certain fluoroelastomer resins and thermosetting powder coatings. It is also used as catalysts in the synthesis of certain organic compounds and as a pharmaceutical intermediate.
- 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.
- it is used as a reagent in solid-state metathesis polycondensation to prepare alkyl-dipropenylthiophene monomers.
- Mizoroki-Heck cyclization and cascading Tsuji-Trost cyclization reactions.
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