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140775 Sigma-Aldrich

Tetrabutylammonium iodide

reagent grade, 98%

Synonym: TBAI

  • CAS Number 311-28-4

  • Linear Formula (CH3CH2CH2CH2)4N(I)

  • Molecular Weight 369.37

  •  Beilstein/REAXYS Number 3916152

  •  EC Number 206-220-5

  •  MDL number MFCD00011636

  •  PubChem Substance ID 24848477

  •  NACRES NA.22

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Properties

Related Categories Ammonium Salts, Chemical Synthesis, Phase Transfer Catalysts, Synthetic Reagents
Quality Level   200
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

Description

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

100 g in poly bottle

25 g in glass bottle

500 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
BS5450000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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