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241059

Sigma-Aldrich

Tetraethylammonium bromide

ReagentPlus®, 99%

Synonym(s):
TEAB, TEA bromide
Linear Formula:
(C2H5)4N(Br)
CAS Number:
Molecular Weight:
210.16
Beilstein:
3563430
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

product line

ReagentPlus®

assay

99%

form

crystals

impurities

1% 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 (TEAB) catalyzes the synthesis of thioesters by the oxidative coupling of aldehydes or alcohols with thiols or disulfides.
  • It is used as a catalyst, along with o-iodoxybenzoic acid (IBX), in the oxidation of sulfides to sulfoxides and primary carboxamides to one-carbon dehomologated nitriles.
  • TEAB can also be used as an organic template to synthesize zeolite beta.

Packaging

50, 250 g in poly bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Hazard Statements

Precautionary Statements

Hazard Classifications

Aquatic Chronic 3

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Tetraethylammonium Bromide-Catalyzed Oxidative Thioesterification of Aldehydes and Alcohols.
Zhu, Xuebin et al.
advanced synthesis and catalysis, 355(18), 3558-3562 (2013)
Masoumeh Taherimehr et al.
ChemSusChem, 10(6), 1283-1291 (2016-12-20)
Metal-organic frameworks (MOFs) with accessible Lewis acid sites are finding increasing application in the field of heterogeneous catalysis. However, the structural instability of MOFs when they are exposed to high temperature and/or high pressure often limits their applicability. In this
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)
Zheng Li et al.
Industrial & engineering chemistry research, 58(34), 15628-15636 (2019-10-11)
The separation of metals by liquid-liquid extraction largely relies on the affinity of metals to the extractants, which normally reside in the organic (less polar) phase because of their high hydrophobicity. Following a different route, using aminopoly(carboxylic acid)s (e.g., EDTA)

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