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Benzyltributylammonium bromide
1. Basic Information
Name: Benzyltributylammonium bromide
Alias: N-Benzyl-N,N,N-tributylbutan-1-aminium bromide, BTBA bromide
CAS No.: 25316-59-0
Molecular Formula: C19H34BrN
Molecular Weight: 356.38
Category: Quaternary ammonium salt phase transfer catalyst (PTC)
2. Physical and Chemical Properties
Physical Properties
- Appearance: White to pale off-white crystalline powder
- Odor: Faint amine-like odor
- Solubility: Soluble in dichloromethane, chloroform, toluene, ethanol, methanol; slightly soluble in water; insoluble in aliphatic alkanes
- Melting Range: 160–164 °C
- Hygroscopy: Slightly hygroscopic under high humidity
- Aqueous Property: Weakly acidic aqueous solution, stable in neutral medium
Chemical Properties
- Molecular Structure: Quaternary ammonium cation with one benzyl group and three n-butyl groups, paired with bromide anion
- Phase Transfer Catalysis: Excellent lipophilic cation, accelerates reactions between aqueous nucleophiles and organic-phase substrates (substitution, alkylation, oxidation, hydrolysis)
- Thermal Stability: Stable below 140 °C; prolonged heating above melting point undergoes Hofmann elimination to form olefin, tributylamine and benzyl bromide
- Photostability: Moderately sensitive to strong UV light; long-term irradiation causes slight yellowing
- Compatibility: Compatible with neutral organic solvents, weak acids/weak bases; incompatible with strong oxidants, concentrated strong alkali, silver salts (generates AgBr precipitate)
3. Main Application Fields
1. Phase Transfer Catalyst (Core Application)
Widely used in fine chemical & pharmaceutical synthesis: halogen substitution, O-alkylation, N-alkylation, epoxidation, cyanation, reduction reactions; effectively improve reaction yield under mild conditions
2. Electrochemical Auxiliary
Supporting electrolyte additive for organic electrolyte systems
3. Antibacterial Auxiliary Raw Material
Intermediate for low-toxicity quaternary ammonium bacteriostatic agents
4. HPLC Reference Standard
Chromatographic standard for quaternary ammonium salt purity testing
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 25316-59-0 |
| Molecular Formula | C19H34BrN |
| Appearance | Uniform white crystalline powder without yellow impurities |
| HPLC Purity | Catalyst Grade ≥99.0% |
| Water Content (KF) | ≤0.30% |
| Melting Range | 160–164 °C |
| Residue on Ignition | ≤0.10% |
| Single Unknown Impurity | ≤0.10% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | Nitrogen-purged amber vacuum aluminum foil bags / PE-lined fiber drums |
| Storage Condition | Hermetically sealed cool dry warehouse below 25 °C; isolated from light, strong oxidants and silver-containing raw materials |
| Transportation Requirement | Mildly hygroscopic quaternary ammonium solid, moisture-proof sealed packaging |
| Shelf Life | 24 months under nitrogen-filled vacuum sealed storage |
Safety Warning
Mild irritant quaternary ammonium salt powder. Dust irritates eyes, respiratory tract and skin; long-term skin contact may cause dryness and allergic redness for sensitive people. All operations shall be carried out in ventilated fume hoods with dust respirators and chemical-resistant gloves. Avoid mixing with silver nitrate to form insoluble bromide precipitate. Waste liquid can be recovered by solvent distillation and neutralized before discharge; solid waste belongs to general organic hazardous waste and disposed by licensed professional hazardous waste treatment facilities.
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