Tetrabutylammonium tribromide 98%Min Dark red to reddish-brown crystalline solid RC00095

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:  www.cnroyalchem.com

Product Name

Tetrabutylammonium Tribromide (TBATB)

Chemical Identifiers

CAS Registry Number:  38932-80-8

EC Number:  254-214-2

Molecular Formula:  C₁₆H₃₆Br₃N or [(CH₃CH₂CH₂CH₂)₄N]⁺Br₃⁻

Molecular Weight:  490.18 g/mol

Synonyms:  TBATB; Tetra-n-butylammonium tribromide; Tribromotetrabutylammonium; n-Bu₄NBr₃

Chemical Structure

Cation:  Tetrabutylammonium [(C₄H₉)₄N]⁺

Anion:  Tribromide [Br₃]⁻ (a linear, symmetric ion: Br-Br-Br⁻)

Physical Description

Appearance:  Dark red to reddish-brown crystalline solid. Often appears as a free-flowing powder or small crystals.

Odor:  Characteristic odor of bromine (especially if decomposed or moist).

Melting Point:  Typically decomposes before melting (~118°C decomposition reported). Does not have a sharp melting point.

Solubility:

Highly soluble in chlorinated organic solvents (dichloromethane, chloroform), acetonitrile, methanol, ethanol.

Moderately soluble in acetone, ethyl acetate.

Sparingly soluble in water; decomposes in aqueous solution.

Density:  ~1.6 g/cm³ (approximate).

Hygroscopicity:  Moderately hygroscopic; absorbs moisture from air, which can lead to decomposition and release of bromine vapor.

Key Properties & Characteristics

Stable Bromine Source:  Acts as a stable, crystalline, and easy-to-handle solid source of "positive bromine" (Br⁺ equivalent) for electrophilic bromination reactions. Safer and more convenient than handling volatile, corrosive liquid bromine (Br₂).

Electrophilic Brominating Agent:  Primarily used for regioselective and stereoselective bromination of alkenes (forming dibromides), alkynes, enol acetates, ketones (alpha-bromination), phenols, anilines, and activated aromatic compounds.

Mild Oxidant:  Can function as an oxidizing agent for specific transformations (e.g., oxidation of alcohols to carbonyls under certain conditions, conversion of sulfides to sulfoxides/sulfones).

Phase-Transfer Catalyst (PTC) Capability:  The tetrabutylammonium cation enables its use as a phase-transfer catalyst, facilitating reactions between reagents in immiscible phases (e.g., aqueous bromine source and organic substrate).

Stoichiometric Reagent:  Typically used stoichiometrically.

Decomposition:  Decomposes upon heating or prolonged exposure to light/moisture, releasing bromine (Br₂) gas. Decomposition in water yields bromide (Br⁻) and bromate (BrO₃⁻) ions.

Handling & Safety

Hazards:

Corrosive:  Causes severe skin burns and eye damage.

Oxidizing:  May intensify fire; oxidizer.

Acute Toxicity:  Harmful if swallowed, inhaled, or in contact with skin. Liberates toxic bromine vapor upon decomposition or reaction with acids/water.

Environmental Hazard:  Toxic to aquatic life.

Precautions:

Handle in a well-ventilated fume hood only.

Wear appropriate PPE: chemical-resistant gloves (nitrile, neoprene), safety goggles, lab coat.

Avoid contact with skin, eyes, and clothing.

Avoid inhalation of dust or vapors.

Keep away from heat, sparks, open flames, and hot surfaces (decomposition/oxidizer risk).

Prevent contact with moisture, acids, reducing agents, and combustible materials.

Storage:

Store tightly sealed in a cool (<25°C), dry, dark place (light-sensitive).

Store under an inert atmosphere (argon, nitrogen) or in a desiccator to minimize moisture absorption and decomposition.

Keep container tightly closed.

Store away from incompatible materials (reducing agents, acids, bases, organics, metals).

Primary Applications

Organic Synthesis:

Electrophilic Bromination:  Regioselective bromination of alkenes (anti-addition), alkynes, enol acetates, ketones (α-bromination), phenols, anilines, activated aromatics.

Oxidation:  Selective oxidation of alcohols (e.g., benzylic alcohols to aldehydes), sulfides to sulfoxides/sulfones.

Cyclization Reactions:  Used in certain bromocyclization reactions.

Dehydrobromination:  Generation of alkynes from vicinal dibromides.

Reagent for Bromine Addition:  Convenient alternative to Br₂ for bromination under milder conditions, often with better selectivity.

Phase-Transfer Catalyst (PTC):  Facilitates bromination/oxidation reactions involving aqueous bromides/hypobromites and organic substrates.

Advantages Over Molecular Bromine (Br₂)

Solid Form:  Easier and safer to weigh, handle, and store.

Reduced Volatility:  Minimizes inhalation hazard and loss of reagent.

Controlled Release:  Bromination can be more controlled and selective.

Solubility:  Often highly soluble in common organic solvents.

PTC Capability:  Enables reactions in biphasic systems.