ChemicalBook > CAS DataBase List > Tetrabutylammonium iodide

Tetrabutylammonium iodide

Product Name
Tetrabutylammonium iodide
CAS No.
311-28-4
Chemical Name
Tetrabutylammonium iodide
Synonyms
TBAI;TETRA-N-BUTYLAMMONIUM IODIDE;Tetrabutylazanium iodide;Tetrabutylammonium i;etrabutylazanium,iodide;%, SLR, Fisher Chemical;Dronedarone Impurity 52;Tetrabutylaminium·iodide;tetrabutyl-ammoniuiodide;Tetrabutylammonium Iodid
CBNumber
CB0187592
Molecular Formula
C16H36IN
Formula Weight
369.37
MOL File
311-28-4.mol
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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)
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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
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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..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
86903
Product name
Tetrabutylammonium iodide
Purity
suitable for ion pair chromatography, LiChropur?, ≥99.0%
Packaging
10g
Price
$185
Updated
2024/03/01
Sigma-Aldrich
Product number
8.22152
Product name
Tetra-n-butylammonium iodide
Purity
for synthesis
Packaging
100g
Price
$72.1
Updated
2024/03/01
Sigma-Aldrich
Product number
140775
Product name
Tetrabutylammonium iodide
Purity
reagent grade, 98%
Packaging
25g
Price
$31
Updated
2024/03/01
Sigma-Aldrich
Product number
8.22152
Product name
Tetra-n-butylammonium iodide
Purity
for synthesis
Packaging
250g
Price
$144
Updated
2024/03/01
Sigma-Aldrich
Product number
140775
Product name
Tetrabutylammonium iodide
Purity
reagent grade, 98%
Packaging
100g
Price
$87.1
Updated
2024/03/01
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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.]

Tetrabutylammonium iodide Preparation Products And Raw materials

Raw materials

Preparation Products

Benzo-15-crown-5 4-Piperazinobenzonitrile N,N-Dimethylethylenediamine 3-Methoxymethylphenylboronic acid (S)-4-BOC-MORPHOLINE-3-CARBOXYLIC ACID S-METHYL-S-BENZYL SULFOXIMINE
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View Lastest Price from Tetrabutylammonium iodide manufacturers

Hebei Longbang Technology Co., Ltd
Product
Tetrabutylammonium iodide 311-28-4
Price
US $6.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20TONS
Release date
2024-05-20
Hebei Zhuanglai Chemical Trading Co Ltd
Product
Tetrabutylammonium iodide 311-28-4
Price
US $50.00/kg
Min. Order
1kg
Purity
99
Supply Ability
5000
Release date
2024-11-19
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Tetrabutylammonium iodide 311-28-4
Price
US $100.00-75.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-21

311-28-4, Tetrabutylammonium iodideRelated Search:

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