140775
Tetrabutylammonium iodide
98%, reagent grade, solid
Synonym(s):
TBAI
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About This Item
Linear Formula:
(CH3CH2CH2CH2)4N(I)
CAS Number:
Molecular Weight:
369.37
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352107
EC Number:
206-220-5
MDL number:
Beilstein/REAXYS Number:
3916152
Product Name
Tetrabutylammonium iodide, reagent grade, 98%
grade
reagent grade
Quality Level
assay
98%
form
solid
reaction suitability
core: ammonium
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
Application
Tetrabutylammonium iodide (TBAI) has been used as a catalyst in the following reactions:
Other reactions where TBAI can be used as a catalyst:
- 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.
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signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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)
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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 140775-25G | 04061838733689 |
| 140775-500G | 04061838733696 |
| 140775-100G | 04061838733672 |