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140775
Tetrabutylammonium iodide
reagent grade, 98%
Synonym(s):
TBAI
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About This Item
Linear Formula:
(CH3CH2CH2CH2)4N(I)
CAS Number:
Molecular Weight:
369.37
Beilstein:
3916152
EC Number:
MDL number:
UNSPSC Code:
12352107
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.
Recommended Products
grade
reagent grade
Quality Level
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:
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.[1]
- Conversion of 8-fluoro-1-aminonaphthalene into 1-(8-fluoro-naphthalen-1-yl)piperazine hydrochloride.[2]
- 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.[3]
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.[4]
- Palladium(0)-catalyzed cross-coupling between benzylic zinc bromides and aryl or alkenyl triflates.[5]
- Three-component coupling of amines, carbon dioxide, and halides to form carbamates in the presence of cesium carbonate.[6]
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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Customers Also Viewed
New Efficient Nickel-and Palladium-Catalyzed Cross-Coupling Reactions Mediated by Tetrabutylammonium Iodide.
Piber M,et al.
Organic Letters, 9(1), 1323-1326 (1999)
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)
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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