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86890

Sigma-Aldrich

Tetrabutylammonium iodide

≥99.0% (AT)

Synonym(s):

TBAI

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(I)
CAS Number:
Molecular Weight:
369.37
Beilstein:
3916152
EC Number:
MDL number:
UNSPSC Code:
12352107
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥99.0% (AT)

form

crystals

mp

141-143 °C (lit.)

SMILES string

[I-].CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/C16H36N.HI/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1

InChI key

DPKBAXPHAYBPRL-UHFFFAOYSA-M

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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.

Application

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J.M. Chong et al.
The Journal of Organic Chemistry, 52, 2596-2596 (1987)
S. Czernecki et al.
Tetrahedron Letters, 3535-3535 (1976)
Fabio Galeotti et al.
Journal of chromatography. A, 1284, 141-147 (2013-03-05)
In this study, by using tetrabutylammonium bisulfate as ion-pairing reagent, we were able to separate all the main heparin/heparan sulfate disaccharides generated by the action of heparinases along with the main Hep tetrasaccharide possessing a 3-O-sulfate group on the sulfoglucosamine
Erbo Shi et al.
Organic letters, 14(13), 3384-3387 (2012-06-27)
A metal-free C-H oxidation for the construction of allylic esters has been developed. The use of a commercially available and inexpensive catalyst and oxidant, and readily available starting materials, coupled with the operational simplicity of the reaction, renders the methodology
Chao Zhong et al.
Carbohydrate polymers, 94(1), 38-45 (2013-04-03)
In this article, a novel and high efficient solvent, tetra-n-Butylammonium Hydroxide (TBAH), was used for dissolution and isolation of straw cellulose from wheat straw. The composition analysis with gas chromatography (GC) and the spectroscopic characterization analysis conducted by X-Ray diffraction

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