15625-56-6

Basic information

• Product Name: Tetramethylammonium tribromide
• Synonyms: TETRAMETHYLAMMONIUM BROMIDE PERBROMIDE;TETRAMETHYLAMMONIUM TRIBROMIDE;n,n,n-trimethyl-methanaminiu(tribromide);Tetramethylammonium tribromide, 98+%;Einecs 239-700-8;Methanaminium, N,N,N-trimethyl-, (tribromide);Methanaminium, N,N,N-trimethyl-, (tribromide) (1:1);Mono(tetramethylammonium) tribromide
• CAS NO: 15625-56-6
• Molecular Formula: Br₃*C₄H₁₂N
• Molecular Weight: 313.86
• EINECS: 239-700-8
• Mol File: 15625-56-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 115-118 °C
• Appearance: /
• Sensitive: Hygroscopic
• BRN: 3914655
• CAS DataBase Reference: Tetramethylammonium tribromide(CAS DataBase Reference)
• NIST Chemistry Reference: Tetramethylammonium tribromide(15625-56-6)
• EPA Substance Registry System: Tetramethylammonium tribromide(15625-56-6)

Safety Data

• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3263 8/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 15625-56-6(Hazardous Substances Data)

Usage

General Description

Tetramethylammonium tribromide is a quaternary ammonium salt with the chemical formula (CH3)4NBr3. It is a yellow-orange crystalline solid that is highly soluble in polar solvents such as water and ethanol. Tetramethylammonium tribromide is primarily used as a brominating reagent in organic synthesis, particularly in the bromination of alkenes and other organic compounds. It is valued for its ability to selectively brominate specific carbon atoms in a molecule, allowing for precise control over the reaction. Tetramethylammonium tribromide is a strong oxidizing agent and must be handled with care due to its potential for causing skin and eye irritation, as well as respiratory irritation if inhaled. Due to its reactivity and handling hazards, it is typically stored and handled in a controlled laboratory setting by trained personnel.

InChI:InChI=1/3C4H12N.3BrH/c3*1-5(2,3)4;;;/h3*1-4H3;3*1H/q3*+1;;;/p-3

Upstream product

• 75-57-0 tetramethlyammonium chloride 
• 64-20-0 tetramethylammonium bromide 

Downstream Products

• 64-18-6 formic acid 
• 463-79-6 carbonic-acid 
• 75-50-3 trimethylamine 
• 7722-84-1 dihydrogen peroxide 
• 15719-64-9 methylammonium carbonate 
• 7726-95-6 bromine 
• 64-20-0 tetramethylammonium bromide 

Relevant articles and documents

Novel Metal- and Mineral-Acid-Free Synthesis of Organic Ammonium Tribromides and Application of Ethylenephenanthrolium Bistribromide for Bromination of Active Methylene Group of 1,3-Diketones and β-Ketoesters

A novel procedure for the preparation of organic ammonium tribromides (OATBs) is described from their corresponding bromides. Quaternary ammonium bromides (QABs) and a N,N′-heterocyclic dibromide are efficiently oxidized to their corresponding monotribromides and bistribromide by m-chloroperbenzoic acid (MCPBA) in the presence of 2 and 4 equiv of KBr, respectively. The reactions are carried out in an aqueous medium without the use of any mineral acid or metal catalyst/promoters. A variety of tribromides are synthesized in very good yields including a hitherto unknown reagent, 1,10-(ethane-1, 2-diyl)phenanthrolinediium bistribromide (EPDBT). EPDBT is investigated as brominating agent and found to be highly effective for selective bromination of active methylene groups of a variety of 1,3-diketones and β-ketoesters. GRAPHICAL ABSTRACT.

Novel method of synthesis of quaternary ammonium tribromides and investigation of catalytic role of benzyltrimethylammonium tribromide in oxidation of alcohols to carbonyl compounds

Stable crystalline organic quaternary ammonium tribromides (QATBs) have been easily synthesized by the oxidation of the corresponding organic ammonium bromides (QABs) with ammonium persulfate. The reactions have been performed under solvent-free conditions in the presence of sulfuric acid and silica as supporting agent. Two equivalents of potassium bromide have been used as the source of additional bromides for quantitative conversion of QABs to QATBs.Ammonium persulfate, a cheap and readily available oxidant, carries out the bromide oxidation to tribromide very effectively under solvent-free conditions. The synthesized QATBs have been shown to catalyze the oxidation of alcohols to carbonyl compounds with hydrogen peroxide as oxidant in good yields under mild reaction conditions. Copyright Taylor & Francis Group, LLC.