79267

Trimethylphenylammonium hydroxide solution

~25% in H₂O (1.68 M)

• 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
• UNSPSC Code: 12352005
• PubChem Substance ID: 57652783
• NACRES: NA.22

Properties

• form: liquid
• Quality Level: 100
• concentration: ~25% in H₂O (1.68 M)
• refractive index: n20/D 1.395
• functional group: amine
• 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

Description

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.

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H314
• Precautionary Statements: P280 - P301 + P330 + P331 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• 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