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Tetramethylammonium hydroxide

Tetramethylammonium hydroxide
TMAH.svg
Names
IUPAC name
tetramethylazanium hydroxide
Other names
tetramethylammonium hydroxide; N,N,N,-trimethylmethanaminium hydroxide
Identifiers
75-59-2 YesY
10424-66-5 (trihydrate) N
10424-65-4 (pentahydrate) N
3D model (Jmol) Interactive image
ChemSpider 54928 YesY
ECHA InfoCard 100.000.803
PubChem 60966
Properties
C4H13NO
Molar mass 91.15 g·mol−1
Density ~ 1.015 g/cm3 (20-25% aqueous solution)
Melting point 67 °C (153 °F; 340 K) (pentahydrate)
Boiling point decomposes
high
Basicity (pKb) 4.2
Hazards
Safety data sheet Sigma-Aldrich MSDS for TMAH·5H2O
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)

GHS signal word Danger
H300, H311, H314, H318
P260, P264, P270, P280, P301+310, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P322, P361, P363, P405
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Related compounds
Other anions
tetramethylammonium chloride
Other cations
tetraethylammonium hydroxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Tetramethylammonium hydroxide (TMAH or TMAOH) is a quaternary ammonium salt with the molecular formula N(CH3)4+ OH−. It is commonly encountered as concentrated solutions in water or methanol. The solid and solutions are colorless, or yellowish if impure. Although TMAH has virtually no odor when pure, samples often have a strongly fishy smell from the trimethylamine which is a common impurity. TMAH has numerous and diverse industrial and research applications.

Anhydrous TMAH has never been isolated. The only relatively stable solid form in which this substance exists is as the pentahydrate, N(CH3)4OH·5H2O, and this has been assigned the CAS# 10424-65-4. A trihydrate, C4H13NO·3H2O, has also been reported, and this has been assigned the CAS# 10424-66-5. TMAH is most commonly encountered as an aqueous solution, in concentrations from ~2–25%, and less frequently as solutions in methanol. These solutions are identified by the CAS# 75-59-2.

One of the earliest preparations of TMAH reported in the literature is that of Walker and Johnston, who made it by the salt metathesis reaction of tetramethylammonium chloride and potassium hydroxide in dry methanol, in which TMAH is soluble, but potassium chloride is not:

Where Me stands for the methyl group, CH3-.

This report also provides details for isolation of TMAH as its pentahydrate, noting the existence of a trihydrate, and emphasizes the avidity which even the former exhibits for atmospheric moisture and carbon dioxide. These authors reported a m.p. of 62–63 °C for the pentahydrate, and a solubility in water of 220 g/100 mL at 15 °C.

TMAH is a very strong base.

One of the industrial uses of TMAH is for the anisotropic etching of silicon. It is used as a basic solvent in the development of acidic photoresist in the photolithography process, and is highly effective in stripping photoresist. TMAH has some phase transfer catalyst properties, and is used as a surfactant in the synthesis of ferrofluid, to inhibit nanoparticle aggregation.


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