Tetrabutylammonium iodide Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P501Dispose of contents/container to..…

Tetrabutylammonium iodide Chemical Properties,Usage,Production

Description

Tetrabutylammonium iodide is a organic ammonium compound, for which all four valences of a nitrogen atom are bonded organically. It is often used as phase-transfer catalysts and ion pair reagents.

Chemical Properties

Tetrabutylammonium iodide is an organic ammonium compound with the molecular formula C16H36IN. white or tan powder. Soluble in water and ethanol, slightly soluble in chloroform and benzene. Stable under normal temperature and pressure.

Uses

Tetrabutylammonium iodide is used in the preparation of novel quaternary amines to serve as antibacterial agents in the rise of drug-resistant bacteria,it is also used in phosphonium reversible inhibitors of cholinesterases.

Application

Tetrabutylammonium iodide may be used as a mobile phase additive in ion-pair high-performance liquid chromatography (IP-HPLC) assay of 4-aminopyridine in serum. It may also be used as a mobile phase additive in the analysis of tetracycline by reversed-phase IPC. The addition of tetrabutylammonium iodide regulates the retention of tetracyclines.
Tetrabutylammonium iodide can be used:
As an additive in the synthesis of fused triazole derivatives using palladium catalyst.
To prepare allyl-PEG-allyl, which is a key intermediate polymer used to synthesize fluorinated amphiphilic copolymers.
As a catalyst used in the synthesis of ethers.

Reactions

Tetrabutylammonium iodide (TBAI) has been used as a catalyst in the following reactions:
Synthesis of O-benzyl-N-Boc-L-tyrosine benzyl ester from N-Boc-L-tyrosine.
Conversion of 8-fluoro-1-aminonaphthalene into 1-(8-fluoro-naphthalen-1-yl)piperazine hydrochloride.
Synthesis of 1-(2,4-dichlorophenyl)-5-(4-(4-iodobut-1-ynyl)phenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide from 4-(4-(1-(2,4-dichlorophenyl)-4-methyl-3-(piperidin-1-ylcarbamoyl)-1H-pyrazol-5-yl)phenyl)but-3-yn-1-yl methanesulfonate.
Other reactions where TBAI can be used as a catalyst:
TBAI-tert-butyl hydroperoxide system can catalyze the conversion of α-methyl styrene derivatives into allylic sulfones by reacting with sulfonylhydrazides under metal-free conditions.
Palladium(0)-catalyzed cross-coupling between benzylic zinc bromides and aryl or alkenyl triflates.
Three-component coupling of amines, carbon dioxide, and halides to form carbamates in the presence of cesium carbonate.

General Description

Tetrabutylammonium iodide is a quaternary ammonium salt used in phase-transfer reactions. It is also used in regioselective ether cleavage reactions and as a source of iodide for nucleophilic displacement reactions.

Flammability and Explosibility

Not classified

Purification Methods

Crystallise the iodide from toluene/pet ether (see entry for the corresponding bromide), acetone, ethyl acetate, EtOH/diethyl ether, nitromethane, aqueous EtOH or water. Dry it at room temperature under a vacuum. It has also been dissolved in MeOH/acetone (1:3, 10mL/g), filtered and allowed to stand at room temperature to evaporate to ca half its original volume. Distilled water (1mL/g) is then added, and the precipitate is filtered off and dried. It can also be dissolved in acetone, precipitated by adding ether and dried in a vacuum at 90o for 2 days. It has also been recrystallised from CH2Cl2/pet ether or hexane, or anhydrous methanol and stored in a vacuum desiccator over H2SO4. [Chau & Espenson J Am Chem Soc 108 1962 1986, Beilstein 4 IV 558.]