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140023

Tetraethylammonium bromide

Name: Tetraethylammonium bromide
Brand: ALDRICH

reagent grade, 98%

Synonym(s):

TEAB, TEA bromide

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About This Item

Linear Formula:

(C₂H₅)₄N(Br)

CAS Number:

71-91-0

Molecular Weight:

210.16

Beilstein:

3563430

EC Number:

200-769-4

MDL number:

MFCD00011825

UNSPSC Code:

12352107

PubChem Substance ID:

24848444

NACRES:

NA.22

grade

reagent grade

Quality Level

200

Assay

98%

form

crystalline

impurities

≤2% triethylamine hydrobromide

pH

6.5 (100 g/L)

mp

285 °C (dec.) (lit.)

SMILES string

[Br-].CC[N+](CC)(CC)CC

InChI

1S/C8H20N.BrH/c1-5-9(6-2,7-3)8-4;/h5-8H2,1-4H3;1H/q+1;/p-1

InChI key

HWCKGOZZJDHMNC-UHFFFAOYSA-M

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Organocatalysts

Application

Tetraethylammonium bromide may be used:

As an organic template for synthesizing zeolite beta via hydrothermal crystallization.
As a catalyst for the oxidative coupling of aldehydes or alcohols with thiophenols or disulfides to form thioesters.
In combination with o-iodoxybenzoic acid (IBX) for the oxidative dehomologation of primary carboxamides to nitriles and α,α-disubstituted acetamides to ketones. This reagent combination can also be used for the conversion of sulfides to sulfoxides and N,N-disubstituted glycylamides into corresponding cyanamides.

Hazard Statements

H412

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 3

WGK

WGK 3

Flash Point(F)

361.4 °F

Flash Point(C)

183 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Oxidative Conversion of ?, ?-Disubstituted Acetamides to Corresponding One-Carbon-Shorter Ketones Using Hypervalent Iodine (?5) Reagents in Combination with Tetraethylammonium Bromide.

Bellale E

The Journal of Organic Chemistry, 73(23), 9473-9475 (2008)

Novel and facile transformation of N, N-disubstituted glycylamides into corresponding cyanamides by using pentavalent iodine reagents in combination with tetraethylammonium bromide.

Chaudhari K

Synlett, 18, 2815-2818 (2007)

A mild, chemoselective oxidation of sulfides to sulfoxides using o-iodoxybenzoic acid and tetraethylammonium bromide as catalyst.

Shukla V

The Journal of Organic Chemistry, 68(13), 5422-5425 (2003)

Hydrothermal crystallization of zeolite beta using tetraethylammonium bromide.

Eapen M

Zeolites, 14(4), 295-302 (1994)

o-Iodoxybenzoic acid-and tetraethylammonium bromide-mediated oxidative transformation of primary carboxamides to one-carbon dehomologated nitriles.

Bhalerao D

The Journal of Organic Chemistry, 72(2), 662-665 (2007)

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