Tetramethylammonium chloride

Tetramethylammonium chloride

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Names
IUPAC name Tetramethylazanium chloride
Other names Tetramethylammonium chloride
Identifiers
CAS Number	75-57-0 Y
ChemSpider	6139 N
Jmol 3D model	Interactive image
PubChem	6379
InChI InChI=1S/C4H12N.ClH/c1-5(2,3)4;/h1-4H3;1H/q+1;/p-1 N Key: OKIZCWYLBDKLSU-UHFFFAOYSA-M N InChI=1/C4H12N.ClH/c1-5(2,3)4;/h1-4H3;1H/q+1;/p-1 Key: OKIZCWYLBDKLSU-REWHXWOFAY
SMILES C[N+](C)(C)C.[Cl-]
Properties
Chemical formula	C4H12NCl
Molar mass	109.60 g/mol
Appearance	White crystals
Density	1.17 g/cm3
Melting point	425 °C (797 °F; 698 K) (decomposes)
Solubility in water	Soluble
Vapor pressure	{{{value}}}
Related compounds
Other anions	tetramethylammonium hydroxide
Other cations	tetraethylammonium chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tetramethylammonium chloride is one of the simplest quaternary ammonium salts, with four methyl groups tetrahedrally attached to the central N. The chemical formula (CH₃)₄N⁺Cl⁻ is often abbreviated further as Me₄N⁺Cl⁻. It is a hygroscopic colourless solid that is soluble in water and polar organic solvents. Tetramethylammonium chloride is a major industrial chemical, being used in such processes as hydrofracking. In the laboratory, it has fewer synthetic chemical applications than quaternary ammonium salts containing longer N-alkyl substituents, which are used extensively as phase-transfer catalysts.

Preparation and laboratory uses

Tetramethylammonium chloride can be synthesized by the alkylation of ammonium chloride with dimethyl carbonate, in the presence of 1-ethyl-3-methyl imidazolium bromide ([EMIM]⁺Br⁻) as an ionic liquid catalyst. The overall reaction is:

NH₄⁺Cl⁻ + 2 (CH₃O)₂CO → N(CH₃)₄⁺Cl⁻ + 2 H₂O + 2 CO₂

Although it can be induced to serve as a methylation reagent, it is typically employed as a source of the inert counter cation Me₄N⁺. Similarly it serves as a lipophilic precipitating agent.

In low concentrations, it is used in polymerase chain reactions to increase yields and specificity. It has been shown to enhance yields 5–10 fold at 60mM by stabilizing the AT base pairs.

Toxicity

LD₅₀ = 25 mg/kg (mouse, i.p.); 40 mg/kg (mouse, s.c.); 50 mg/kg (rat, p.o.). Very toxic to aquatic organisms.

Diverse data on human exposure, environmental toxicology and environmentally-related chemistry is available through the NIH Toxnet database.

See also

• Quaternary ammonium cation
• Tetraethylammonium chloride
• Tetramethylammonium hydroxide
• Tetramethylammonium