140023

Sigma-Aldrich

Tetraethylammonium bromide

reagent grade, 98%

Synonym(s):
TEAB, TEA bromide
Linear Formula:
(C2H5)4N(Br)
CAS Number:
Molecular Weight:
210.16
Beilstein/REAXYS Number:
3563430
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

grade

reagent grade

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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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.

Packaging

250 g in poly bottle
1 kg in poly bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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)
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)
Tetraethylammonium Bromide?Catalyzed Oxidative Thioesterification of Aldehydes and Alcohols.
Zhu X
Advanced Synthesis & Catalysis, 355(18), 3558-3562 (2013)
Hydrothermal crystallization of zeolite beta using tetraethylammonium bromide.
Eapen M
Zeolites, 14(4), 295-302 (1994)
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)

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