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140023

Sigma-Aldrich

Tetraethylammonium bromide

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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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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

140023-250G:
140023-VAR:
140023-5G:
140023-BULK:
140023-1KG:

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD6364V
WXBD5182V
WXBD2522V
WXBD0361V
WXBC9354V

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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)
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)
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)
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