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Sigma-Aldrich

Trimethylphenylammonium hydroxide solution

~25% in H2O (1.68 M)

Synonym(s):

Phenyltrimethylammonium hydroxide, TMAH

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About This Item

Linear Formula:
(CH3)3N(OH)C6H5
CAS Number:
1899-02-1
Molecular Weight:
153.22
Beilstein:
3917033
MDL number:
MFCD00041899
UNSPSC Code:
12352005
PubChem Substance ID:
57652783
NACRES:
NA.22

form

liquid

concentration

~25% in H2O (1.68 M)

refractive index

n20/D 1.395

SMILES string

[OH-].C[N+](C)(C)c1ccccc1

InChI

1S/C9H14N.H2O/c1-10(2,3)9-7-5-4-6-8-9;/h4-8H,1-3H3;1H2/q+1;/p-1

InChI key

HADKRTWCOYPCPH-UHFFFAOYSA-M

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General description

Trimethylphenylammonium hydroxide solution (TMPAH) is a quaternary ammonium compound that is commonly used as a strong base in organic synthesis. It is also used as a deprotecting agent for the removal of t-butoxycarbonyl (Boc) groups from amino acids or peptides and benzyl protecting groups from alcohols or amines.

Application

Trimethylphenylammonium hydroxide solution can be used to initiate the polymerization of the monomer 1,8-dihydroxymethyl-1,3,5,7-octatetrayne (DHOT) for the preparation of polymer nanospheres. It is also used as a base in the synthesis of alkyl 3-nitroacrylates via aldol reaction with nitroacetaldehyde or nitroacetone.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Fazel Abdolahpur Monikh et al.
Nature communications, 12(1), 899-899 (2021-02-11)
Analytical limitations considerably hinder our understanding of the impacts of the physicochemical properties of nanomaterials (NMs) on their biological fate in organisms. Here, using a fit-for-purpose analytical workflow, including dosing and emerging analytical techniques, NMs present in organisms are characterized
Estefanía Noriega-Fernández et al.
Foods (Basel, Switzerland), 10(3) (2021-04-04)
The aim of this work was to evaluate the potential of ultrasound (US), alone or in combination with mild heating and/or EDTA towards reduction of As, Cd, I, and Hg content of Laminaria hyperborea. Concentrations of As, Cd, I, and
Seungjoon Chung et al.
International journal of environmental research and public health, 17(12) (2020-06-25)
This study describes an immobilization method of enriched microorganism, for robustly degrading organic compounds, including tetramethyl ammonium hydroxide (TMAH) in electronics wastewater without an increase of total organic carbon (TOC) in effluent. The enriched TMAH degrading bacteria was entrapped inside
Timothy J Jensen et al.
Journal of photochemistry and photobiology. B, Biology, 100(2), 100-111 (2010-06-19)
Five cationic porphyrins bearing one to four -N(CH(3))(3)(+) groups linked to the p-phenyl positions of 5,10,15,20-tetraphenylporphyrin (TPP) were synthesized in order to study the effect of overall charge and its distribution on the cellular uptake, phototoxicity and intracellular localization using
Y El-Nahhal et al.
Journal of agricultural and food chemistry, 48(10), 4791-4801 (2000-10-29)
This study aimed to design formulations of hydrophobic herbicides, alachlor and metolachlor, by adsorbing them on the clay mineral montmorillonite preadsorbed by the small organic cation phenyltrimethylammonium (PTMA). An adsorption model that considers electrostatics and specific binding and the possibility
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