4317-07-1

Basic information

• Product Name: TETRAETHYLPHOSPHONIUM BROMIDE
• Synonyms: TETRAETHYLPHOSPHONIUM BROMIDE;TETRAETHYLPHOSPHONIUM BROMIDE 97%;HISHICOLIN PX-2B
• CAS NO: 4317-07-1
• Molecular Formula: Br*C₈H₂₀P
• Molecular Weight: 227.12
• Product Categories: Phosphonium Salts;Phosphonium Compounds
• Mol File: 4317-07-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 333-335 °C(lit.)
• Appearance: /
• Water Solubility: almost transparency in Water
• CAS DataBase Reference: TETRAETHYLPHOSPHONIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAETHYLPHOSPHONIUM BROMIDE(4317-07-1)
• EPA Substance Registry System: TETRAETHYLPHOSPHONIUM BROMIDE(4317-07-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• F: 3-8-10
• Hazardous Substances Data: 4317-07-1(Hazardous Substances Data)

Usage

General Description

Tetraethylphosphonium bromide is a quaternary ammonium compound with the chemical formula (C2H5)4PBr. It is a colorless or white crystalline solid that is highly soluble in water. Tetraethylphosphonium bromide is commonly used as a phase-transfer catalyst in organic synthesis, which facilitates the transfer of substrates between immiscible solvents by forming a complex with the reaction substrates. It is also used as a reagent in organic reactions, and as an intermediate in the production of other organic compounds. Additionally, tetraethylphosphonium bromide has applications in electrochemistry, as an electrolyte in batteries, and in the preparation of nanomaterials. Due to its toxicity and potential environmental impact, it is important to handle and dispose of tetraethylphosphonium bromide in accordance with safety regulations and guidelines.

InChI:InChI=1/C8H20P.BrH/c1-5-9(6-2,7-3)8-4;/h5-8H2,1-4H3;1H/q+1;/p-1

Upstream product

• 7664-93-9 sulfuric acid 
• 117961-64-5 triethyl-(2-bromo-ethyl)-phosphonium; triethyl-(β-bromo-ethyl)-phosphonium bromide 
• 74-96-4 ethyl bromide 
• 554-70-1 triethylphosphine 
• 4317-06-0 tetraethylphosphonium iodide 
• 925-90-6 ethylmagnesium bromide 

Relevant articles and documents

Synthesis of monophosphines directly from white phosphorus

Monophosphorus compounds are of enormous industrial importance due to the crucial roles they play in applications such as pharmaceuticals, photoinitiators and ligands for catalysis, among many others. White phosphorus (P4) is the key starting material for the preparation of all such chemicals. However, current production depends on indirect and inefficient, multi-step procedures. Here, we report a simple, effective ‘one-pot’ synthesis of a wide range of organic and inorganic monophosphorus species directly from P4. Reduction of P4 using tri-n-butyltin hydride and subsequent treatment with various electrophiles affords compounds that are of key importance for the chemical industry, and it requires only mild conditions and inexpensive, easily handled reagents. Crucially, we also demonstrate facile and efficient recycling and ultimately catalytic use of the tributyltin reagent, thereby avoiding the formation of substantial Sn-containing waste. Accessible, industrially relevant products include the fumigant PH3, the reducing agent hypophosphorous acid and the flame-retardant precursor tetrakis(hydroxymethyl)phosphonium chloride. [Figure not available: see fulltext.]

Effect of Cation on Physical Properties and CO2 Solubility for Phosphonium-Based Ionic Liquids with 2-Cyanopyrrolide Anions

A series of tetraalkylphosphonium 2-cyanopyrrolide ([Pnnnn][2-CNPyr]) ionic liquids (ILs) were prepared to investigate the effect of cation size on physical properties and CO2 solubility. Each IL was synthesized in our laboratory and characterized by NMR spectroscopy. Their physical properties, including density, viscosity, and ionic conductivity, were determined as a function of temperature and fit to empirical equations. The density gradually increased with decreasing cation size, while the viscosity decreased noticeably. In addition, the [Pnnnn][2-CNPyr] ILs with large cations exhibited relatively low degrees of ionicity based on analysis of the Walden plots. This implies the presence of extensive ion pairing or formation of aggregates resulting from van der Waals interactions between the long hydrocarbon substituents. The CO2 solubility in each IL was measured at 22 °C using a volumetric method. While the anion is typically known to be predominantly responsible for the CO2 capture reaction, the [Pnnnn][2-CNPyr] ILs with shorter alkyl chains on the cations exhibited slightly stronger CO2 binding ability than the ILs with longer alkyl chains. We attribute this to the difference in entropy of reaction, as well as the variation in the relative degree of ionicity.