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Sigma-Aldrich

Trimethylphenylammonium hydroxide solution

~25% in H2O (1.68 M)

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Synonym(s):
Phenyltrimethylammonium hydroxide, TMAH
Linear Formula:
(CH3)3N(OH)C6H5
CAS Number:
1899-02-1
Molecular Weight:
153.22
Beilstein:
3917033
MDL number:
MFCD00041899
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

Regulatory Information

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