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Merck
CN

86890

Sigma-Aldrich

Tetrabutylammonium iodide

≥99.0% (AT), crystals

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
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Product Name

Tetrabutylammonium iodide, ≥99.0% (AT)

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

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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)
Oliver Bixner et al.
The Journal of chemical physics, 136(20), 204503-204503 (2012-06-07)
The interaction of exciton and charge transfer (CT) states plays a central role in photo-induced CT processes in chemistry, biology, and physics. In this work, we use a combination of two-dimensional electronic spectroscopy (2D-ES), pump-probe measurements, and quantum chemistry to
Mei Shen et al.
Journal of the American Chemical Society, 134(24), 9856-9859 (2012-06-05)
Here we report on the unprecedentedly high resolution imaging of ion transport through single nanopores by scanning electrochemical microscopy (SECM). The quantitative SECM image of single nanopores allows for the determination of their structural properties, including their density, shape, and
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

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