Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 20:17, 7 October 2010 editCitation bot (talk | contribs)Bots5,391,782 editsm Citations: added: last2, first2, last3, first3, last4, first4. Rjwilmsi← Previous edit		Latest revision as of 17:46, 19 July 2023 edit undoBernardirfan (talk | contribs)Extended confirmed users10,991 edits Clarification
(59 intermediate revisions by 39 users not shown)
Line 1:		Line 1:
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 309647040
			| Watchedfields = changed
⚫	| ImageFileR1 = Tetramethylammonium-chloride-ion-pair-2D.png
		⚫	| verifiedrevid = 389387218
	| ImageSizeR1 = 180px
	| ImageFileL1 = Tetramethylammonium-3D-balls.png		| ImageFile1 = Tetramethylammonium-chloride-ion-pair-2D.png
			| ImageFile2 = Tetramethylammonium-3D-balls.png
	| ImageSizeL1 = 120
	| IUPACName = Tetramethylammonium chloride		| ImageCaption2 = ] ion. Blue: nitrogen, black: carbon, white: hydrogen
		⚫	| ImageFile3 = Tetramethylammonium chloride.jpg
	| OtherNames =
			| PIN = ''N'',''N'',''N''-Trimethylmethanaminium chloride
⚫	| Section1 = {{Chembox Identifiers
			| OtherNames = Tetramethylammonium chloride<br />Tetramethylazanium chloride
	| CASNo = 75-57-0
		⚫	|Section1={{Chembox Identifiers
⚫	| CASNo_Ref = {{cascite}}
	| PubChem =		| CASNo = 75-57-0
		⚫	| CASNo_Ref = {{cascite|correct|CAS}}
⚫	| SMILES = C(C)(C)C.
			| 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(C)(C)C.
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>4</sub>H<sub>12</sub>NCl		| Formula = C<sub>4</sub>H<sub>12</sub>NCl
	| MolarMass = 109.60 g/mol		| MolarMass = 109.60&nbsp;g/mol
	| Appearance = White crystals		| Appearance = White crystals
	| Density = 1.17 g/cm<sup>3</sup>		| Density = 1.17&nbsp;g/cm<sup>3</sup>
	| MeltingPt = 425 °C (dec)		| MeltingPtC = 425
			| MeltingPt_notes = (decomposes)
	| BoilingPt =
	| Solubility = Soluble		| BoilingPt =
			| SolubleOther = Soluble in water and methanol. Slightly soluble in ethanol. Insoluble in ether, benzene, chloroform.
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
	| MainHazards =		| MainHazards =
	| FlashPt =		| FlashPt =
	| Autoignition =		| AutoignitionPt =
	| RPhrases =		| HPhrases =
	| SPhrases =		| PPhrases =
			| GHS_ref =
	}}		}}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
	| OtherAnions = ]		| OtherAnions = ]
	| OtherCations = ]		| OtherCations = ] chloride
	}}		}}
	}}		}}
			'''Tetramethylammonium chloride''' is one of the simplest ], with four ] groups tetrahedrally attached to the central N. The chemical formula (CH<sub>3</sub>)<sub>4</sub>N<sup>+</sup>Cl<sup>−</sup> is often abbreviated further as Me<sub>4</sub>N<sup>+</sup>Cl<sup>−</sup>. It is a ] colourless solid that is soluble in water and polar organic ]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 ].<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 ].
	'''Tetramethylammonium chloride''' is a ] with the chemical formula Cl. It is a colourless solid that is soluble in water and polar organic solvents. Tetramethylammonium chloride has few applications, unlike quaternary ammonium salts that feature more longer alkyl substituents.
	==Preparation and laboratory uses==		==Preparation and laboratory uses==
			Tetramethylammonium chloride is efficiently produced by the reaction of ] and ].<ref>{{Ullmann |doi=10.1002/14356007.a16_535|title=Methylamines|year=2000|last1=Van Gysel|first1=August B.|last2=Musin|first2=Willy}}</ref>
⚫	Tetramethylammonium chloride can be synthesized by the ] of ] with ].<ref>{{Cite journal | last1 = Zheng | first1 = Z. ''et al.'' | 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 | url = | journal = Advanced Synthesis & Catalysis | volume = 349 | issue = | pages = 1095–1101 | doi = 10.1002/adsc.200600451 }}</ref>
		⚫	:N(CH<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>Cl → N(CH<sub>3</sub>)<sub>4</sub><sup>+</sup>Cl<sup>−</sup>
		⚫	It is produced by the ] of ] with ] in the presence of an ] 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>
⚫	:Cl<sup>−</sup> + 2 (CH<sub>3</sub>O)<sub>2</sub>CO → Cl<sup>−</sup> + 2 H<sub>2</sub>O + 2 CO<sub>2</sub>
			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 K<sub>2</sub>CO<sub>3</sub> or Cs<sub>2</sub>CO<sub>3</sub>|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 Me<sub>4</sub>N<sup>+</sup>. Similarly, it serves as a lipophilic ] agent.<ref>{{OrgSynth
	It is used in organic synthesis for methylation and occasionally as a precipitating agent.<ref>{{OrgSynth
	|author=W. J. Middleton and D. W. Wiley		| author =W. J. Middleton and D. W. Wiley
	|year=1973		| year =1973
	|title=tetramethylammonium 1-Propene-1,1,2,3,3-pentacarbonitrile		| title =tetramethylammonium 1-Propene-1,1,2,3,3-pentacarbonitrile
			| volume =
	|volume=
			| pages =
	|pages=
			| collvol =5
	|collvol=5
			| collvolpages =1013
	|collvolpages=1013
	|prep=CV5P1013}}</ref>		| doi =10.15227/orgsyn.041.0099}}</ref>
	In low concentrations, it is used with polymerase chain reactions to increase yield and specificity. It has been shown to enhance yield 5-10 fold at 3M 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): 3343-3344</ref>		In low concentrations, it is used in ]s to increase yields and specificity. It has been shown to enhance yields 5–10 fold at 60] by stabilizing the AT ].<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==
			LD<sub>50</sub> = 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 ] Toxnet database.<ref name = Toxnet/>
	==See also==		==See also==
	* ]		* ]
			* ]
	* ]		* ]
			* ]
	== References ==		==References==
	{{reflist}}		{{Reflist}}
	]
	{{organic-compound-stub}}
			]
	]