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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/REAXYS Number:
3917033
MDL number:
MFCD00041899
UNSPSC Code:
12352005
PubChem Substance ID:
57652783
NACRES:
NA.22

form

liquid

Quality Level

100

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

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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
R W Gullick et al.
Environmental science & technology, 35(7), 1523-1530 (2001-05-12)
A natural shale and four synthetic organoclays were compared as potential sorbent additives to containment barriers at hazardous waste sites. Trimethylphenyl ammonium bentonite (TMPA-bent) was shown in batch experiments to have the greatest sorption capacities for 1,2,4-trichlorobenzene, trichloroethylene, and methyl
Jeffrey T Auletta et al.
Chemico-biological interactions, 187(1-3), 135-141 (2010-05-25)
Acetylcholinesterase (AChE) contains a narrow and deep active site gorge with two sites of ligand binding, an acylation site (or A-site) at the base of the gorge and a peripheral site (or P-site) near the gorge entrance. The P-site contributes
Anthony A Mikulec et al.
Otology & neurotology : official publication of the American Otological Society, American Neurotology Society [and] European Academy of Otology and Neurotology, 30(2), 131-138 (2009-01-31)
Drugs applied to the middle ear enter perilymph through the bony otic capsule. Drugs applied intratympanically in humans are thought to enter the cochlea primarily through the round window membrane (RWM). Local drug treatments of the ear are commonly evaluated
Alec N Salt et al.
Journal of the Association for Research in Otolaryngology : JARO, 13(6), 771-783 (2012-09-13)
Perilymph pharmacokinetics was investigated by a novel approach, in which solutions containing drug or marker were injected from a pipette sealed into the perilymphatic space of the lateral semi-circular canal (LSCC). The cochlear aqueduct provides the outlet for fluid flow
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