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Tetramethylammonium information


Tetramethylammonium
Names
Preferred IUPAC name
N,N,N-Trimethylmethanaminium[1]
Other names
Tetramethylammonium[1]
Tetramethylazanium
Tetramine
Identifiers
CAS Number
  • 51-92-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:46020 checkY
ChemSpider
  • 6140 checkY
PubChem CID
  • 6380
UNII
  • H0W55235FC checkY
CompTox Dashboard (EPA)
  • DTXSID3048071 Edit this at Wikidata
InChI
  • InChI=1S/C4H12N/c1-5(2,3)4/h1-4H3/q+1
    Key: QEMXHQIAXOOASZ-UHFFFAOYSA-N
SMILES
  • C[N+](C)(C)C
Properties
Chemical formula
C4H12N+
Molar mass 74.14 g/mol
Related compounds
Related isoelectronic
neo-pentane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tetramethylammonium (TMA) is the simplest quaternary ammonium cation. It has the chemical formula [Me4N]+ and consists of four methyl groups (−CH3, denoted Me) attached to a central nitrogen atom. The cation is isoelectronic with neopentane (Me4C). It is positively-charged and can only be isolated in association with a counter-ion. Common salts include tetramethylammonium chloride and tetramethylammonium hydroxide. Tetramethylammonium salts are used in chemical synthesis and in pharmacological research. It confers no color to its salts.

  1. ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 1086. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

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Tetramethylammonium

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Tetramethylammonium (TMA) is the simplest quaternary ammonium cation. It has the chemical formula [Me4N]+ and consists of four methyl groups (−CH3, denoted...

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Tetramethylammonium hydroxide

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Tetramethylammonium hydroxide (TMAH or TMAOH) is a quaternary ammonium salt with molecular formula N(CH3)4+ OH−. It is commonly encountered in form of...

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Tetramethylammonium fluoride

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Tetramethyl­ammonium fluoride is the quaternary ammonium salt with the formula (CH3)4NF. This hygroscopic white solid is a source of “naked fluoride":...

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Tetramethylammonium perchlorate

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Tetramethylammonium perchlorate is a perchlorate salt with a condensed formula [N(CH3)4]+ClO4−. Tetramethylammonium perchlorate can be produced by mixing...

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Tetramethylammonium chloride

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Tetramethylammonium chloride is one of the simplest quaternary ammonium salts, with four methyl groups tetrahedrally attached to the central N. The chemical...

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Tetramethylammonium pentafluoroxenate

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Tetramethylammonium pentafluoroxenate is a chemical compound with the chemical formula [N(CH3)4]+[XeF5]−. This salt consists of tetramethylammonium cations...

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Tetramethylammonium auride

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Tetramethylammonium auride, (CH3)4NAu, is an ionic compound containing tetramethylammonium as cation and gold in a –1 oxidation state as anion. It is an...

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Potassium superoxide

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chlorides to diacyl peroxides. Ion exchange with tetramethylammonium hydroxide gives tetramethylammonium superoxide, a yellow solid. The Russian Space Agency...

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Gold

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crystallizes in the caesium chloride motif; rubidium, potassium, and tetramethylammonium aurides are also known. Gold has the highest electron affinity of...

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Quaternary ammonium cation

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latter is indicated by the stability of the hydroxide salts such as tetramethylammonium hydroxide and tetrabutylammonium hydroxide even at elevated temperatures...

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Isopropyl alcohol

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of monocrystalline silicon, such as with potassium hydroxide or tetramethylammonium hydroxide. This process is used in texturing of silicon solar cells...

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Methylation

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sources such as iodomethane, dimethyl sulfate, dimethyl carbonate, or tetramethylammonium chloride. Less common but more powerful (and more dangerous) methylating...

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Hypertension

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World War, the most popular and reasonably effective of which were tetramethylammonium chloride, hexamethonium, hydralazine, and reserpine (derived from...

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Carbanion

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of the corresponding organosodium reagent with tetramethylammonium chloride. Since tetramethylammonium cations cannot form a chemical bond to the carbanionic...

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Lignin

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break down of a substance under vacuum and at high temperature) with tetramethylammonium hydroxide (TMAH) or cupric oxide has also been used to characterize...

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Tetranitratoborate

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formula [B(NO3)4]−. It can form salts with large cations such as tetramethylammonium nitratoborate, or tetraethylammonium tetranitratoborate. The ion...

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Caesium auride

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plane. Solutions undergo metathesis with tetramethylammonium loaded ion exchange resin to give tetramethylammonium auride. Kienast, Gerhard; Verma, Jitendra;...

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Tetraethylammonium chloride

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tetraethylammonium, tetramethylammonium, and N,N-dimethyl-pyrrolidinium fluoride monohydrates, tetraethylammonium chloride monohydrate, and tetramethylammonium hydroxide...

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Hydrogen bond

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the fact that trimethylammonium hydroxide is a weaker base than tetramethylammonium hydroxide. The description of hydrogen bonding in its better-known...

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Trimethylamine

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and carnitine. Trimethylamine is used in the synthesis of choline, tetramethylammonium hydroxide, plant growth regulators, herbicides, strongly basic anion...

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Fluoride

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nucleophile. Some quaternary ammonium salts of naked fluoride include tetramethylammonium fluoride and tetrabutylammonium fluoride. Cobaltocenium fluoride...

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Houttuynia cordata

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of Houttuynia cordata Thunb by Using On-Column Methylation with Tetramethylammonium Acetate". Journal of AOAC International. 90 (1): 60–67. doi:10.1093/jaoac/90...

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Tetraethylammonium cyanide

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prepared similarly. The salt is highly toxic. Tetraethylammonium Tetramethylammonium chloride Entley, William R.; Treadway, Christopher R.; Wilson, Scott...

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Bulk micromachining

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uses alkaline liquid solvents, such as potassium hydroxide (KOH) or tetramethylammonium hydroxide (TMAH) to dissolve silicon which has been left exposed...

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