Tetraethylammonium bromide

Base Information

• Chemical Name: Tetraethylammonium bromide
• CAS No.: 71-91-0
• Deprecated CAS: 65129-07-9,65129-11-5,65129-11-5
• Molecular Formula: C8H20BrN
• Molecular Weight: 210.157
• Hs Code.: 29239000
• European Community (EC) Number: 200-769-4
• NSC Number: 36724
• UNII: 0435621Z3N
• DSSTox Substance ID: DTXSID9044457
• Wikipedia: Tetraethylammonium_bromide
• Wikidata: Q5961420
• NCI Thesaurus Code: C152577
• ChEMBL ID: CHEMBL324254
• Mol file: 71-91-0.mol

Synonyms:Bromide, Tetraethylammonium;Chloride, Tetraethylammonium;Hydroxide, Tetraethylammonium;Iodide, Tetraethylammonium;Ion, Tetraethylammonium;Tetraethylammonium;Tetraethylammonium Bromide;Tetraethylammonium Chloride;Tetraethylammonium Hydroxide;Tetraethylammonium Iodide;Tetraethylammonium Ion

Chemical Property of Tetraethylammonium bromide

Chemical Property:

• Appearance/Colour: white to light yellow crystalline solid
• Melting Point: 285 °C (dec.)(lit.)
• Refractive Index: 1,442-1,444
• PSA: 0.00000
• Density: 1.397 g/cm³
• LogP: -1.11320
• Storage Temp.: Store at room temperature.
• Sensitive.: Hygroscopic
• Solubility.: acetonitrile: 0.1 g/mL warm, clear, colorless
• Water Solubility.: 2795 g/L (25 º C)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 209.07791
• Heavy Atom Count: 10
• Complexity: 47.5

Purity/Quality:

99% ^*data from raw suppliers

Tetraethylammonium bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Quaternary Amines
• Canonical SMILES: CC[N+](CC)(CC)CC.[Br-]
• General Description: Tetraethylammonium bromide (TEAB) is a quaternary ammonium salt used as a supporting electrolyte in electrochemical reactions, such as the Hg cathode-free detosylation of N,N-disubstituted p-toluenesulfonamides, where it facilitates efficient deprotection under mild conditions. It also serves as a competitive agent in stability studies of self-folding resorcin[4]arene derivatives, demonstrating low association constants due to the high stability of intramolecular inclusion complexes. Additionally, TEAB acts as a key reagent in oxidative dehomologation reactions, where it combines with hypervalent iodine (λ5) reagents to convert α,α-disubstituted acetamides into one-carbon-shorter ketones via an N-bromoimine intermediate. Its versatility in synthetic and electrochemical applications highlights its utility in organic transformations.

Technology Process of Tetraethylammonium bromide

There total 21 articles about Tetraethylammonium bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.6%

trans-2-bromobutenedioic acid dimethyl ester (2509-16-2) + triethylamine (121-44-8) → tetraethylammonium bromide (71-91-0) + dimethyl diethylaminofumarate (996-85-0,98033-35-3)

Guidance literature:

In acetonitrile; for 7h; Heating;

Reference yield: 98.0%

ethyl bromide (74-96-4) + triethylamine (121-44-8) → tetraethylammonium bromide (71-91-0)

Guidance literature:

In acetonitrile; at 60 ℃; for 72h;

DOI:10.1002/open.201900217

Reference yield: 60.0%

(Et4N)2{Mo3(μ3-S)(μ2-S2)3Br6} → (PPh3)3Mo3(μ3-S)(μ2-S)3Br4 + tetraethylammonium bromide (71-91-0) + triphenylphosphine sulfide (3878-45-3)

Guidance literature:

With P(C₆H₅)3; In methanol; Stirring of a suspn. of Mo-compd. and PPh3 (MeOH, 1 h).; Filtn. of pptd. green solid, washing with hot MeOH and benzene, drying (vac.), elem. anal.;

DOI:10.1016/S0020-1693(00)83936-5

upstream raw materials:

ethyl bromide

triethylamine

diethyl sulfate

cis+trans-dibromoethylene

Downstream raw materials:

[1,3]-dioxolan-2-one

tetraethylammonium bis<α,α-bis(trifluoromethyl)benzenemethanolato (2-)-C²,O>(4-methoxyphenyl)silicate(1-)

tetraethylammonium bis<α,α-bis(trifluoromethyl)benzenemethanolato (2-)-C²,O><3-(trifluoromethyl)phenyl>silicate(1-)

N(C₂H₅)4⁽¹⁺⁾*P(C₆H₅)2CS₂^(1-)=[N(C₂H₅)4][P(C₆H₅)2CS₂]

Refernces

Hg cathode-free electrochemical detosylation of N,N-disubstituted p-toluenesulfonamides: mild, efficient, and selective removal of N-tosyl group

10.1016/j.tetlet.2009.11.056

The purpose of this study was to achieve mild, efficient, and selective removal of the N-tosyl group, a protecting group for primary and secondary amines, under neutral and mild conditions without the use of harmful and toxic reagents. The researchers successfully carried out the deprotection using constant current electrolysis with an undivided cell equipped with a platinum cathode and a magnesium anode, in the presence of an arene mediator, such as naphthalene or biphenyl. The process resulted in the corresponding secondary amines in good to excellent yields, demonstrating the efficiency of the method and its potential as a powerful tool for the synthesis of various nitrogen-containing organic compounds. The chemicals used in this process include N,N-disubstituted p-toluenesulfonamides, platinum, magnesium, and an arene mediator, along with a supporting electrolyte, Et4NBr, in DMF solvent.

Synthesis of resorcin[4]arene bearing self-folding substituent

10.1016/j.tetlet.2011.04.085

The research focuses on the synthesis of a monofunctionalized resorcin[4]arene derivative through thiomethylation using N,N-diisopropyl-2-aminoethanethiol hydrochloride and formaldehyde in methanol/acetic acid at 60°C. The introduced substituent self-includes into the cavity of the resorcin[4]arene, reducing the reactivity of the aromatic rings and inhibiting further functionalization. The study explores the reaction conditions and yields, with the optimal conditions yielding the monofunctionalized product in 68%. The 1H NMR and 13C NMR spectra provide evidence of the self-inclusion of the substituent, with the interaction being intramolecular. The stability of the self-inclusion complex is examined through competitive complexation experiments with tetraethylammonium bromide, revealing a low association constant indicative of high stability. The research concludes that the self-inclusion of the substituent plays a dominant role in controlling the selectivity of the reaction, and further studies on novel resorcin[4]arene derivatives are underway.

Oxidative conversion of α,α-disubstituted acetamides to corresponding one-carbon-shorter ketones using hypervalent iodine (λ⁵) reagents in combination with tetraethylammonium bromide

10.1021/jo801580g

The study, titled "Oxidative Conversion of r,r-Disubstituted Acetamides to Corresponding One-Carbon-Shorter Ketones Using Hypervalent Iodine (λ5) Reagents in Combination with Tetraethylammonium Bromide," investigates a novel method for converting R,R-disubstituted acetamides into ketones that are one carbon atom shorter. The key chemicals involved are hypervalent iodine (λ5) reagents, specifically o-iodoxybenzoic acid (IBX) and Dess-Martin periodinane (DMP), and tetraethylammonium bromide (TEAB). These reagents are used to oxidatively dehomologate R,R-disubstituted acetamides, resulting in the formation of ketones. The study establishes a mild, efficient, and general method for this transformation, with IBX and TEAB in acetonitrile at 60 °C yielding the best results. The researchers also explored the reaction mechanism, proposing that an N-bromoimine intermediate forms during the process, which subsequently hydrolyzes to produce the ketone.