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Merck

86890

Tetrabutylammonium iodide

≥99.0% (AT), crystals

Synonym(s):

TBAI

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(I)
CAS Number:
311-28-4
Molecular Weight:
369.37
NACRES:
NA.22
PubChem Substance ID:
57653211
UNSPSC Code:
12352107
EC Number:
206-220-5
MDL number:
MFCD00011636
Beilstein/REAXYS Number:
3916152

Key Documents

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Product Name

Tetrabutylammonium iodide, ≥99.0% (AT)

InChI key

DPKBAXPHAYBPRL-UHFFFAOYSA-M

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

SMILES string

[I-].CCCC[N+](CCCC)(CCCC)CCCC

assay

≥99.0% (AT)

form

crystals

Quality Level

200

reaction suitability

core: ammonium

mp

141-143 °C (lit.)

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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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Gloves

flash_point_f

No data available

flash_point_c

No data available

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP4227
BCCN8375
BCCN1688
BCCM3006
BCCK4555

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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)
Chao Zhong et al.
Carbohydrate polymers, 94(1), 38-45 (2013-04-03)
In this article, a novel and high efficient solvent, tetra-n-Butylammonium Hydroxide (TBAH), was used for dissolution and isolation of straw cellulose from wheat straw. The composition analysis with gas chromatography (GC) and the spectroscopic characterization analysis conducted by X-Ray diffraction
David J Posson et al.
Nature structural & molecular biology, 20(2), 159-166 (2012-12-25)
Understanding how ion channels open and close their pores is crucial for comprehending their physiological roles. We used intracellular quaternary ammonium blockers, electrophysiology and X-ray crystallography to locate the voltage-dependent gate in MthK potassium channels from Methanobacterium thermoautotrophicum. Blockers bind
Zhenfeng He et al.
Dalton transactions (Cambridge, England : 2003), 41(33), 10043-10051 (2012-05-29)
A new kind of organic-inorganic hybrid complexes based on polyoxometalate were synthesized through symmetrically grafting two adeninyl groups onto Anderson-type MnMo(6) clusters and encapsulating the clusters by organic surfactants. The resultant complexes exhibited thermal-induced dynamic self-assembly behaviors which greatly depended
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