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Sigma-Aldrich

Tetraethylammonium hydroxide solution

~25% in methanol (~1.5 M)

Synonym(s):

TEA hydroxide

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About This Item

Linear Formula:
(C2H5)4N(OH)
CAS Number:
77-98-5
Molecular Weight:
147.26
Beilstein:
3912961
MDL number:
MFCD00009024
UNSPSC Code:
12352100
PubChem Substance ID:
57653059
NACRES:
NA.22

form

liquid

Quality Level

100

concentration

~25% in methanol (~1.5 M)

anion traces

sulfate (SO42-): ≤1000 mg/kg

SMILES string

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

InChI

1S/C8H20N.H2O/c1-5-9(6-2,7-3)8-4;/h5-8H2,1-4H3;1H2/q+1;/p-1

InChI key

LRGJRHZIDJQFCL-UHFFFAOYSA-M

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General description

Tetraethylammonium hydroxide (TEAOH) is a quaternary ammonium salt that is commonly used as a strong base and phase-transfer catalyst in organic synthesis.

Application

Tetraethylammonium hydroxide (25% in methanol) can be used as a base in the synthesis of 2-hydroxyacetophenoxime from 2-hydroxysalicylaldoxime and hydroxylamine hydrochloride. It is also used as an organic structure-directing agent in the synthesis of zeolites such as Beta, ZSM-20, and SAPO-34.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 1

Target Organs

Eyes,Central nervous system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

49.5 °F

Flash Point(C)

9.7 °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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Jayabalan Nirmal et al.
Experimental eye research, 116, 27-35 (2013-07-31)
The present study was conducted to test the hypothesis; OCT may be active from blood-to-vitreous for the uptake of its substrates. Ocular uptake of Tetraethylammonium (TEA) across blood ocular barriers and the tissue distribution was evaluated in vivo in New
Nanomechanics of cation-π interactions in aqueous solution.
Qingye Lu et al.
Angewandte Chemie (International ed. in English), 52(14), 3944-3948 (2013-03-02)
Lei Yang et al.
The Journal of general physiology, 140(5), 529-540 (2012-10-31)
We investigated the effects of changing extracellular K(+) concentrations on block of the weak inward-rectifier K(+) channel Kir1.1b (ROMK2) by the three intracellular cations Mg(2+), Na(+), and TEA(+). Single-channel currents were monitored in inside-out patches made from Xenopus laevis oocytes
Ling Xiao et al.
Circulation research, 112(10), 1310-1322 (2013-03-28)
A chromosomal haplotype producing cardiac overexpression of dipeptidyl peptidase-like protein-6 (DPP6) causes familial idiopathic ventricular fibrillation. The molecular basis of transient outward current (I(to)) in Purkinje fibers (PFs) is poorly understood. We hypothesized that DPP6 contributes to PF I(to) and
Samuel J Goodchild et al.
The Journal of general physiology, 140(5), 495-511 (2012-10-17)
The open state of voltage-gated potassium (Kv) channels is associated with an increased stability relative to the pre-open closed states and is reflected by a slowing of OFF gating currents after channel opening. The basis for this stabilization is usually
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