Tetramethylammonium chloride: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 389387218

| ImageFile1 = Tetramethylammonium-chloride-ion-pair-2D.png

| ImageFile2 = Tetramethylammonium-3D-balls.png

| ImageCaption2 = [[Tetramethylammonium]] ion. Blue: nitrogen, black: carbon, white: hydrogen

| ImageFile3 = Tetramethylammonium chloride.jpg

| PIN = ''N'',''N'',''N''-Trimethylmethanaminium chloride

| OtherNames = Tetramethylammonium chloride<br />Tetramethylazanium chloride

|Section1={{Chembox Identifiers

| CASNo = 75-57-0

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = DCQ9S88703

| PubChem = 6379

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 6139

| InChI = 1/C4H12N.ClH/c1-5(2,3)4;/h1-4H3;1H/q+1;/p-1

| InChIKey = OKIZCWYLBDKLSU-REWHXWOFAY

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C4H12N.ClH/c1-5(2,3)4;/h1-4H3;1H/q+1;/p-1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = OKIZCWYLBDKLSU-UHFFFAOYSA-M

| SMILES = C[N+](C)(C)C.[Cl-]

|Section2={{Chembox Properties

| Formula = C₄H₁₂NCl

| MolarMass = 109.60&nbsp;g/mol

| Appearance = White crystals

| Density = 1.17&nbsp;g/cm³

| MeltingPtC = 425

| MeltingPt_notes = (decomposes)

| BoilingPt =

| SolubleOther = Soluble in water and methanol. Slightly soluble in ethanol. Insoluble in ether, benzene, chloroform.

|Section3={{Chembox Hazards

| ExternalSDS = [http://msds.chem.ox.ac.uk/TE/tetramethylammonium_chloride.html External MSDS]

| MainHazards =

| FlashPt =

| AutoignitionPt =

| HPhrases =

| PPhrases =

| GHS_ref =

}}

|Section8={{Chembox Related

| OtherCations = [[tetraethylammonium]] chloride

'''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 [[solvent]]s. Tetramethylammonium chloride is a major industrial chemical, being used widely as a chemical reagent<ref name = Toxnet>{{Cite web |url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+7987 |title=Tetramethylammonium chloride - National Library of Medicine HSDB Database |access-date=2012-09-24 |archive-date=2015-12-22 |archive-url=https://web.archive.org/web/20151222014215/http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+7987 |url-status=dead }}</ref> and also as a low-residue bactericide in such processes as [[hydrofracking]].<ref>{{Cite web |url=http://fracfocus.org/chemical-use/what-chemicals-are-used |title=What Chemicals Are Used &#124; FracFocus Chemical Disclosure Registry |access-date=2012-10-30 |archive-date=2013-08-14 |archive-url=https://web.archive.org/web/20130814180235/http://fracfocus.org/chemical-use/what-chemicals-are-used |url-status=dead }}</ref> 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]].

Tetramethylammonium chloride is efficiently produced by the reaction of [[trimethylamine]] and [[Chloromethane|methyl chloride]].<ref>{{Ullmann |doi=10.1002/14356007.a16_535|title=Methylamines|year=2000|last1=Van Gysel|first1=August B.|last2=Musin|first2=Willy}}</ref>

:N(CH₃)₃ + CH₃Cl → N(CH₃)₄⁺Cl⁻

It is produced by the [[alkylation]] of [[ammonium chloride]] with [[dimethyl carbonate]] in the presence of an [[ionic liquid]] catalyst.<ref>{{Cite journal | last1 = Zheng | first1 = Z. | last2 = Wang | year = 2007 | first2 = Jie | last3 = Wu | first3 = Ting Hua | last4 = Zhou | first4 = Xiao Ping | title = Alkylation of Ammonium Salts Catalyzed by Imidazolium-Based Ionic Liquid Catalysts | journal = Advanced Synthesis & Catalysis | volume = 349 | issue = 7| pages = 1095–1101 | doi = 10.1002/adsc.200600451 |display-authors=etal}}</ref>

Except under extraordinary conditions,<ref>{{cite journal|last1=Nenad|first1=Maraš|last2=Polanc|first2=Slovenko|last3=Kočevar|first3=Marijan|title=Microwave-assisted methylation of phenols with tetramethylammonium chloride in the presence of K₂CO₃ or Cs₂CO₃|journal=Tetrahedron|date=2008|volume=64|issue=51|pages=11618–11624|doi=10.1016/j.tet.2008.10.024}}</ref> it is typically employed as a source of the inert counter cation Me₄N⁺. Similarly, it serves as a lipophilic [[Precipitation (chemistry)|precipitating]] agent.<ref>{{OrgSynth

| author =W. J. Middleton and D. W. Wiley

| year =1973

| title =tetramethylammonium 1-Propene-1,1,2,3,3-pentacarbonitrile

| volume =

| pages =

| collvol =5

| collvolpages =1013

| doi =10.15227/orgsyn.041.0099}}</ref>

In low concentrations, it is used in [[polymerase chain reaction]]s to increase yields and specificity. It has been shown to enhance yields 5–10 fold at 60[[Molar concentration#millimolar|mM]] by stabilizing the AT [[base pairs]].<ref>Chevet E. et al. (1995). "Low concentrations of tetramethylammonium chloride increase yield and specificity of PCR". ''Nucleic Acids Research'' '''23''' (16) 3343–344.</ref>

==Toxicity==

LD₅₀ = 25&nbsp;mg/kg (mouse, i.p.); 40&nbsp;mg/kg (mouse, s.c.); 50&nbsp;mg/kg (rat, p.o.). Very toxic to aquatic organisms.<ref>{{cite web|url=https://datasheets.scbt.com/sc-251199.pdf|title=Tetramethylammonium chloride|website=Datasheets.scbt.com|access-date=14 March 2022}}</ref>

Diverse data on human exposure, environmental toxicology and environmentally-related chemistry is available through the [[NIH]] Toxnet database.<ref name = Toxnet/>

* [[Tetraethylammonium chloride]]

* [[Tetramethylammonium]]

==References==

{{Reflist}}

[[Category:Tetramethylammonium salts]]