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140775

Sigma-Aldrich

Tetrabutylammonium iodide

reagent grade, 98%

Synonym(s):

TBAI

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(I)
CAS Number:
311-28-4
Molecular Weight:
369.37
Beilstein:
3916152
EC Number:
206-220-5
MDL number:
MFCD00011636
UNSPSC Code:
12352107
PubChem Substance ID:
24848477
NACRES:
NA.22

grade

reagent grade

Assay

98%

form

solid

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319

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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Tetrabutylammonium iodide catalyzed allylic sulfonylation of α-methyl styrene derivatives with sulfonylhydrazides.
Li X Xu X and Zhou C
Chemical Communications (Cambridge, England), 48(100), 12240-12242 (2012)
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)
New Efficient Nickel-and Palladium-Catalyzed Cross-Coupling Reactions Mediated by Tetrabutylammonium Iodide.
Piber M,et al.
Organic Letters, 9(1), 1323-1326 (1999)
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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