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241059

Sigma-Aldrich

Tetraethylammonium bromide

ReagentPlus®, 99%

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:
24854459
NACRES:
NA.22

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.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Hazard Statements

H412

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 3

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

361.4 °F - closed cup

Flash Point(C)

183 °C - closed cup

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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Tetraethylammonium Bromide-Catalyzed Oxidative Thioesterification of Aldehydes and Alcohols.
Zhu, Xuebin et al.
advanced synthesis and 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)
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
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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