All Photos(2)

140775

Sigma-Aldrich

Tetrabutylammonium iodide

reagent grade, 98%

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

Quality Level

grade

reagent grade

assay

98%

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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Application

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.

Packaging

500 g in glass bottle
25 g in glass bottle
100 g in poly bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

New Efficient Nickel-and Palladium-Catalyzed Cross-Coupling Reactions Mediated by Tetrabutylammonium Iodide.
Piber M,et al.
Organic Letters, 9(1), 1323-1326 (1999)
Solid-phase asymmetric synthesis using a polymer-supported chiral Evans'-type oxazolidin-2-one.
Green R, et al.
Nature Protocols, 8(10), 1890-1890 (2013)
Efficient carbamate synthesis via a three-component coupling of an amine, CO2, and alkyl halides in the presence of Cs2CO3 and tetrabutylammonium iodide.
Salvatore R N, et al.
The Journal of Organic Chemistry, 66(3), 1035-1037 (2001)
Crystal structure of the human cannabinoid receptor CB 1.
Hua T, et al.
Cell, 167(3), 750-762 (2016)
Practical Alternative Synthesis of 1-(8-Fluoro-naphthalen-1-yl) piperazine.
Zhu Z, et al.
Organic Process Research & Development, 11(5), 907-909 (2007)

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