86890
Tetrabutylammonium iodide
≥99.0% (AT)
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
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Quality Level
Assay
≥99.0% (AT)
form
crystals
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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General description
Tetrabutylammonium iodide is a quaternary ammonium salt used in phase-transfer reactions. It is also used in regioselective ether cleavage reactions and as a source of iodide for nucleophilic displacement reactions.
Application
Tetrabutylammonium iodide can be used:
- As an additive in the synthesis of fused triazole derivatives using palladium catalyst.
- To prepare allyl-PEG-allyl, which is a key intermediate polymer used to synthesize fluorinated amphiphilic copolymers.
- As a catalyst used in the synthesis of ethers.
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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J.M. Chong et al.
The Journal of Organic Chemistry, 52, 2596-2596 (1987)
S. Czernecki et al.
Tetrahedron Letters, 3535-3535 (1976)
Fabio Galeotti et al.
Journal of chromatography. A, 1284, 141-147 (2013-03-05)
In this study, by using tetrabutylammonium bisulfate as ion-pairing reagent, we were able to separate all the main heparin/heparan sulfate disaccharides generated by the action of heparinases along with the main Hep tetrasaccharide possessing a 3-O-sulfate group on the sulfoglucosamine
Erbo Shi et al.
Organic letters, 14(13), 3384-3387 (2012-06-27)
A metal-free C-H oxidation for the construction of allylic esters has been developed. The use of a commercially available and inexpensive catalyst and oxidant, and readily available starting materials, coupled with the operational simplicity of the reaction, renders the methodology
R Bryan Sears et al.
Journal of inorganic biochemistry, 121, 77-87 (2013-01-29)
The complex cis-[Ru(phpy)(phen)(CH3CN)2](+) (phpy=2-phenylpyridine, phen=1,10-phenanthroline) was investigated as a potential photodynamic therapy (PDT) agent. This complex presents desirable photochemical characteristics including a low energy absorption tail extending into the PDT window (600-850nm) and photoinduced exchange of the CH3CN ligands, generating
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