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86890

Sigma-Aldrich

Tetrabutylammonium iodide

≥99.0% (AT)

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Synonym(s):
TBAI
Linear Formula:
(CH3CH2CH2CH2)4N(I)
CAS Number:
Molecular Weight:
369.37
Beilstein/REAXYS Number:
3916152
EC Number:
MDL number:
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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1 of 4

This Item
42628814077586868
vibrant-m

86890

Tetrabutylammonium iodide

vibrant-m

426288

Tetrabutylammonium bromide

vibrant-m

140775

Tetrabutylammonium iodide

vibrant-m

86868

Tetrabutylammonium bisulfate

assay

≥99.0% (AT)

assay

≥98.0%

assay

98%

assay

≥99.0% (T)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

mp

141-143 °C (lit.)

mp

102-106 °C (lit.)

mp

141-143 °C (lit.)

mp

169-173 °C

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

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Customers Also Viewed

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
Morteza Moradi et al.
The Analyst, 137(15), 3549-3557 (2012-06-27)
Hollow fiber-based liquid phase microextraction (HF-LPME) using conventional solvents is limited by their relative instability and high volatility. The use of supramolecular solvents as a liquid membrane phase could overcome these inconveniences due to their negligible vapour pressure and high

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