Tetrabutylammonium iodide (TBAI) is a widely used phase transfer catalyst that enhances reaction rates and facilitates a broad range of chemical transformations. It can also serve as an iodine source, generating iodide in situ to replace unstable or costly iodide reagents. Furthermore, TBAI is extensively applied in the dealkylation of esters and ethers.
Tetrabutylammonium iodide Chemical Properties
| Melting point | 141-143 °C(lit.) |
| Boiling point | 145.3℃[at 101 325 Pa] |
| Density | 1.20 |
| Vapor pressure | 0Pa at 25℃ |
| Storage temp. | Store below +30°C. |
| Solubility | Acetonitrile: 0.1 g/mL, clear, colorless |
| Form | Crystalline Powder |
| Color | White to cream |
| Odor | Amine like |
| Water Solubility | Soluble in water and methanol. Insoluble in benzene. |
| Sensitive | Light Sensitive & Hygroscopic |
| λmax | λ: 290 nm Amax: 0.1 λ: 300 nm Amax: 0.05 λ: 320 nm Amax: 0.02 λ: 500 nm Amax: 0.02 |
| BRN | 3916152 |
| Exposure limits | ACGIH: TWA 0.01 ppm |
| Stability | Stable. Incompatible with strong oxidizing agents. Light-sensitive. |
| InChIKey | DPKBAXPHAYBPRL-UHFFFAOYSA-M |
| LogP | 0.869 at 25℃ |
| CAS DataBase Reference | 311-28-4(CAS DataBase Reference) |
| EPA Substance Registry System | Tetrabutylammonium iodide (311-28-4) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22-36/37/38 |
| Safety Statements | 26-36-37/39 |
| WGK Germany | 3 |
| RTECS | BS5450000 |
| F | 8 |
| TSCA | Yes |
| HS Code | 29239000 |
| Toxicity | LD50 orally in Rabbit: 1990 mg/kg |
TBAI, as a phase transfer catalyst, can efficiently facilitate the alkylation of nucleophilic substrates such as alcohols, amines, and phospholipids. Its catalytic effect becomes particularly significant in two-phase reaction systems, where it plays a crucial role in driving the reaction forward.
