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Revision as of 12:27, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 418144121 of page Tert-Butyl_chloride for the Chem/Drugbox validation project (updated: '').		Latest revision as of 19:33, 27 October 2022 edit Citation bot (talk | contribs)Bots5,391,851 edits Misc citation tidying. | Use this bot. Report bugs. | Suggested by AManWithNoPlan | #UCB_CommandLine
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		⚫	{{DISPLAYTITLE:''tert''-Butyl chloride}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 418142714		| verifiedrevid = 470602836
⚫	| Name=''tert''-Butyl chloride
			| Name =''tert''-Butyl chloride
	| ImageFileL1 = Tert-butyl-chloride-2D-skeletal.png		| ImageFileL1 = Tert-butyl-chloride-2D-skeletal.png
	| ImageSizeL1 = 100px
	| ImageFileR1 = Tert-butyl-chloride-3D-balls.png		| ImageFileR1 = Tert-butyl-chloride-3D-balls.png
			| ImageFile2 = Tert butyl chloride.jpg
	| ImageSizeR1 = 120px
			| ImageSize2 = 50px
	| IUPACName = 2-chloro-2-methylpropane		| PIN = 2-Chloro-2-methylpropane
	| OtherNames = 1,1-dimethylethyl chloride<br/>1-chloro-1,1-dimethylethane<br/>chlorotrimethylmethane<br/>trimethylchloromethane<br/>''t''-butyl chloride		| OtherNames = 1,1-dimethylethyl chloride<br/>1-chloro-1,1-dimethylethane<br/>chlorotrimethylmethane<br/>trimethylchloromethane<br/>''t''-butyl chloride
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 346997		| ChEMBL = 346997
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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	| StdInChIKey = NBRKLOOSMBRFMH-UHFFFAOYSA-N		| StdInChIKey = NBRKLOOSMBRFMH-UHFFFAOYSA-N
	| CASNo = 507-20-0		| CASNo = 507-20-0
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| EC-number = 208-066-4
			| UNII = JN2YO95TZ0
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	| EC_number = 208-066-4
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 10054		| ChemSpiderID = 10054
	| PubChem = 10486		| PubChem = 10486
	| SMILES = ClC(C)(C)C		| SMILES = ClC(C)(C)C
	| RTECS = TX5040000		| RTECS = TX5040000
	| UNNumber = 1127		| UNNumber = 1127
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>4</sub>H<sub>9</sub>Cl		| Formula = C<sub>4</sub>H<sub>9</sub>Cl
	| MolarMass = 92.57 g/mol		| MolarMass = 92.57 g/mol
	| Appearance = Colorless liquid		| Appearance = Colorless liquid
	| Density = 0.84 g cm<sup>−3</sup>		| Density = 0.851 g/ml
	| MeltingPtC = −26		| MeltingPtC = −26
	| BoilingPtC = 51		| BoilingPtC = 51
	| Solubility = Sparingly sol in water, miscible with alcohol and ether		| Solubility = Sparingly soluble in water, miscible with alcohol and ether
	| VaporPressure = 34.9 kPa (20 °C)		| VaporPressure = 34.9 kPa (20 °C)
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
			| FlashPtC = −9
	| EUClass = Flammable ('''F''')
		⚫	| FlashPt_notes = (open cup)<br>−23 °C (closed cup)
	| MainHazards =
			| AutoignitionPtC = 540
⚫	| FlashPt = −9 °C (open cup)<br>−23 °C (closed cup)
		⚫	| NFPA-H = 2
	| Autoignition = 540 °C
	| NFPA-H = 2		| NFPA-F = 3
	| NFPA-F = 3		| NFPA-R = 0
			| GHSPictograms = {{GHS02}}
⚫	| NFPA-R = 0
	| NFPA-O =		| GHSSignalWord = Danger
	| RPhrases = {{R12}}, {{R36/37/38}}		| HPhrases = {{H-phrases|225}}
			| PPhrases = {{P-phrases|210|233|240|241|242|243|280|303+361+353|370+378|403+235|501}}
	| SPhrases = {{S7}}, {{S9}}, {{S16}}, {{S29}}, {{S33}}
	}}		}}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
	| Function = ]s		| OtherFunction_label = ]s
	| OtherFunctn = ]		| OtherFunction = ]
	}}		}}
	}}		}}
			'''''tert''-Butyl chloride''' is the ] with the formula {{chem2|(CH3)3CCl}}. It is a colorless, flammable liquid. It is sparingly soluble in ], with a tendency to undergo ] to the corresponding ''tert''-butyl alcohol. It is produced industrially as a precursor to other organic compounds.<ref name=Ullmann>M. Rossberg et al. "Chlorinated Hydrocarbons" in ''Ullmann's Encyclopedia of Industrial Chemistry'' 2006, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a06_233.pub2}}</ref>
			== Synthesis ==
			''tert''-Butyl chloride is produced by the reaction of ''tert''-butyl alcohol with ].<ref name=Ullmann/> In the laboratory, concentrated ] is used. The conversion entails a S<sub>N</sub>1 reaction as shown below.<ref>James F. Norris and Alanson W. Olmsted "''tert''-Butyl Chloride" Org. Synth. 1928, volume 8, pp. 50. {{doi|10.15227/orgsyn.008.0050}}</ref>
			{| class="wikitable" style="text-align:center;"
			| '''Step 1'''||'''Step 2'''||'''Step 3'''
			|-
			| ]||]||]
			|-
			| The acid protonates the alcohol, forming a good ] (water).||Water leaves the protonated ''t''-BuOH, forming a relatively stable tertiary ].||The chloride ion attacks the carbocation, forming ''t''-BuCl.
			|}
			The overall reaction, therefore, is:
			:{{chem2|(CH3)3COH + HCl -> (CH3)3CCl + H2O}}
			Because ''tert''-butanol is a tertiary alcohol, the relative stability of the ''tert''-butyl carbocation in the step 2 allows the ] mechanism to be followed, whereas a primary alcohol would follow an ] mechanism.
			==Reactions==
			When ''tert''-butyl chloride is dissolved in water, it undergoes a ] to ]. When dissolved in alcohols, the corresponding t-butyl ethers are produced.
			==Uses==
			''tert''-Butyl chloride is used to prepare the antioxidant ''tert''-butylphenol and the fragrance neohexyl chloride.<ref name=Ullmann/>
			== See also ==
			* ]
			==References==
			<references />
			== External links ==
			*
			*
			*
			{{DEFAULTSORT:Butyl chloride, tert-}}
			]
			]