Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Tert-Butyl alcohol: Difference between pages

{{DISPLAYTITLE:''tert''-Butyl alcohol}}

| verifiedrevid = 470602673

| Name = ''tert''-Butyl alcohol

| ImageFile =

| ImageFileL1 = Tert-butyl-alcohol-2D-skeletal.svg

| ImageSizeL1 = 110

| ImageNameL1 = Skeletal formula of ''tert''-butyl alcohol

| ImageFileR1 = Tert-Butanol molecule ball from xtal.png

| ImageSizeR1 = 130

| ImageNameR1 = Ball and stick model of ''tert''-butyl alcohol

| ImageFile2 = TBuOH_1133.jpg

| ImageFile2_Ref = {{chemboximage|correct|??}}

| ImageName2 = Sample of partially crystallized ''tert''-butyl alcohol

| PIN = 2-Methylpropan-2-ol <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->

| SystematicName =

| OtherNames = {{bulletedlist|''t''-Butyl alcohol|''tert''-Butanol|''t''-Butanol|''t''-BuOH|Trimethyl carbinol<ref name=PGCH/>|Tertiary butanol|2-Methyl-2-propanol|2M2P}}

| IUPACName =

| Section1 = {{Chembox Identifiers

| CASNo = 75-65-0

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

| PubChem = 6386

| ChemSpiderID = 6146

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

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

| UNII = MD83SFE959

| EINECS = 200-889-7

| UNNumber = 1120

| DrugBank = DB03900

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| MeSHName = tert-Butyl+Alcohol

| ChEBI = 45895

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 16502

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| RTECS = EO1925000

| Beilstein = 906698

| Gmelin = 1833

| SMILES = CC(C)(C)O

| StdInChI = 1S/C4H10O/c1-4(2,3)5/h5H,1-3H3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = DKGAVHZHDRPRBM-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| Section2 = {{Chembox Properties

| C=4 | H=10 | O=1

| Density = 0.775 g/mL

| Appearance = Colorless solid

| Odor = Camphorous

| MeltingPtK = 298 to 299

| BoilingPtK = 355 to 356

| LogP = 0.584

| pKa = 16.54 <ref>{{cite journal|last1=Reeve |first1=W. |last2=Erikson |first2=C. M. |last3=Aluotto |first3=P. F. |title=tert-Butyl alcohol|journal=Can. J. Chem. |date=1979 |volume=57 |page=2747|doi=10.1139/v79-444 |doi-access=free }}</ref>

| Solubility = miscible<ref>{{cite web|url=http://www.inchem.org/documents/icsc/icsc/eics0114.htm|title=ICSC 0114 – ''tert''-Butanol|website=Inchem.org|access-date=29 March 2018}}</ref>

| VaporPressure = 4.1 kPa (at 20 °C)

| RefractIndex = 1.387

| MagSus = {{val|5.742|e=-5|u=cm³/mol}}

| Dipole = 1.31 D

| Section3 = {{Chembox Thermochemistry

| DeltaHf = −360.04 to −358.36 kJ&nbsp;mol⁻¹

| DeltaHc = −2.64479 to −2.64321 MJ&nbsp;mol⁻¹

| Entropy = 189.5 J&nbsp;K⁻¹&nbsp;mol⁻¹

| HeatCapacity = 215.37 J&nbsp;K⁻¹&nbsp;mol⁻¹

| Section4 = {{Chembox Hazards

| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0114.htm inchem.org]

| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}

| GHSSignalWord = '''DANGER'''

| HPhrases = {{H-phrases|225|319|332|335}}

| PPhrases = {{P-phrases|210|261|305+351+338}}

| NFPA-H = 2

| NFPA-F = 3

| NFPA-R = 0

| FlashPtC = 11

| AutoignitionPtC = 480

| ExploLimits = 2.4–8.0%

| PEL = TWA 100&nbsp;ppm (300 mg/m³)<ref name=PGCH>{{PGCH|0078}}</ref>

| IDLH = 1600&nbsp;ppm<ref name=PGCH/>

| REL = TWA 100&nbsp;ppm (300&nbsp;mg/m³) ST 150&nbsp;ppm (450&nbsp;mg/m³)<ref name=PGCH/>

| LD50 = 3559 mg/kg (rabbit, oral)<br/>3500 mg/kg (rat, oral)<ref>{{IDLH|75650|tert-Butyl alcohol}}</ref>

| Section5 = {{Chembox Related

| OtherFunction_label = [[butanol]]s

| OtherFunction = [[2-Butanol]]<br />

[[Isobutanol]]

| OtherCompounds = [[2-Methyl-2-butanol]] <br /> [[Trimethylsilanol]] <br />

[[Nonafluoro-tert-butyl alcohol]]

| Section6 =

'''''tert''-Butyl alcohol''' is the simplest [[Alcohol (chemistry)#Systematic names|tertiary alcohol]], with a [[chemical formula|formula]] of (CH₃)₃COH (sometimes [[skeletal formula#Pseudoelement symbols|represented]] as ''t''-BuOH). Its [[isomer]]s are [[1-butanol]], [[isobutanol]], and [[butan-2-ol]]. ''tert''-Butyl alcohol is a colorless solid, which melts near room temperature and has a [[camphor]]-like odor. It is miscible with [[water]], [[ethanol]] and [[diethyl ether]].

==Natural occurrence==

''tert''-Butyl alcohol has been identified in [[beer]] and [[chickpea]]s.<ref>{{cite web|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+50|title=''t''-Butyl Alcohol |website=National Library of Medicine HSDB Database|publisher=National Institute for Health|access-date=29 March 2018}}</ref> It is also found in [[cassava]],<ref>{{cite web |url=http://www.sc.mahidol.ac.th/scbc/bc_internet/publication/696.pdf |title=Archived copy |access-date=2013-03-05 |url-status=dead |archive-url=https://web.archive.org/web/20160304032348/http://www.sc.mahidol.ac.th/scbc/bc_internet/publication/696.pdf |archive-date=2016-03-04 }}</ref> which is used as a fermentation ingredient in certain [[Alcoholic beverage#Beverages by fermentation ingredients|alcoholic beverages]].

==Preparation==

''tert''-Butyl alcohol is derived commercially from [[isobutane]] as a coproduct of [[propylene oxide]] production. It can also be produced by the catalytic [[hydration reaction|hydration]] of [[isobutylene]], or by a [[Grignard reaction]] between [[acetone]] and [[methylmagnesium chloride]].

Purification cannot be performed by simple distillation due to formation of an [[azeotrope]] with water, although initial drying of the solvent containing large amounts of water is performed by adding benzene to form a tertiary azeotrope and distilling off the water. Smaller amounts of water are removed by drying with [[calcium oxide]] (CaO), [[potassium carbonate]] (K₂CO₃), [[calcium sulfate]] (CaSO₄), or [[magnesium sulfate]] (MgSO₄), followed by fractional distillation. Anhydrous ''tert''-butyl alcohol is obtained by further refluxing and distilling from magnesium activated with iodine, or alkali metals such as sodium or potassium. Other methods include the use of 4&nbsp;[[ångström|Å]] [[molecular sieve]]s, [[aluminium tert-butylate|aluminium ''tert''-butylate]], [[calcium hydride]] (CaH₂), or fractional crystallization under inert atmosphere.<ref>{{cite book | title = Purification of Laboratory Chemicals | url = https://archive.org/details/purificationofla0000perr_n7w5 | url-access = registration | edition = 3rd | first1 = D. D. | last1 = Perrin | first2 = W. L. F. | last2 = Armarego | date = 1988 | publisher = Pergamon Press| isbn = 9780080347141 }}</ref>

==Applications==

''tert''-Butyl alcohol is used as a solvent, ethanol [[denatured alcohol|denaturant]], [[paint remover]] ingredient, and [[gasoline]] [[octane rating|octane]] booster and [[oxygenate]]. It is a chemical intermediate used to produce [[Methyl tert-butyl ether|methyl ''tert''-butyl ether]] (MTBE) and [[Ethyl tert-butyl ether|ethyl ''tert''-butyl ether]] (ETBE) by reaction with [[methanol]] and [[ethanol]], respectively, and [[Tert-Butyl hydroperoxide|''tert''-butyl hydroperoxide]] (TBHP) by reaction with [[hydrogen peroxide]].

==Reactions==

Unlike other isomers of butanol, ''tert''-butyl alcohol, as a tertiary alcohol, has no hydrogen atom next to hydroxy-group, which makes it resistant to oxidation to carbonyl compounds.

''tert''-Butyl alcohol is deprotonated with a strong [[base (chemistry)|base]] to give the [[alkoxide]]. Particularly common is [[potassium tert-butoxide|potassium ''tert''-butoxide]], which is prepared by treating ''tert''-butanol with [[potassium]] metal.<ref>{{OrgSynth | first1 = W. S. | last1 = Johnson | first2 = W. P. | last2 = Schneider | title = β-Carbethoxy-γ,γ-diphenylvinylacetic acid | doi= 10.15227/orgsyn.030.0018 | year = 1950 | volume = 30 | pages = 18 | collvol = | collvolpages = }}</ref>

:K + ''t''-BuOH → ''t''-BuO⁻K⁺ + {{sfrac|1|2}}&nbsp;H₂

The ''tert''-butoxide is a strong, non-[[nucleophilic]] base in organic chemistry. It readily abstracts acidic protons from substrates, but its steric bulk inhibits the group from participating in [[nucleophilic substitution]], such as in a [[Williamson ether synthesis]] or an [[SN2|S_N2]] reaction.

''tert''-Butyl alcohol reacts with [[hydrogen chloride]] to form [[tert-Butyl chloride|''tert''-butyl chloride]].

O-Chlorination of tert-butyl alcohol with hypochlorous acid to give [[tert-butyl hypochlorite]]:<ref>{{cite journal|title=t-Butyl Hypochlorite

|first1=H. M.|last1=Mintz|first2=C.|last2=Walling|journal=Org. Synth.|year=1969|volume=49|page=9|doi=10.15227/orgsyn.049.0009}}</ref>

:(CH₃)₃COH + HOCl → (CH₃)₃COCl + H₂O

==Pharmacology and toxicology==

There is limited data on the pharmacology and toxicology of tert-butanol in humans and other animals.<ref>{{Cite journal | author = Douglas McGregor | title = Tertiary-Butanol: a toxicological review | journal = [[Critical Reviews in Toxicology]] | volume = 40 | issue = 8 | pages = 697–727 | year = 2010 | doi = 10.3109/10408444.2010.494249 | pmid = 20722584| s2cid = 26041562 }}</ref> Human exposure may occur due to fuel oxygenate metabolism. Tert-butanol is poorly absorbed through skin but rapidly absorbed if inhaled or ingested. Tert-butanol is irritating to skin or eyes. Toxicity of single doses is usually low but high doses can produce a sedative or anesthetic effect.

==References==

{{reflist}}

==External links==

*{{ICSC|0114|01}}

*{{PGCH|0078}}

*{{EHC|65|name=Butanols: four isomers}}

*{{HSG|id=007|number=7|name=''tert''-Butanol|date=1987|isbn=92-4-154565-8}}

{{Alcohols}}

{{Sedatives}}

{{GABAAR PAMs}}

{{Glycinergics}}

{{Authority control}}

{{DEFAULTSORT:Butyl alcohol, tert}}

[[Category:Alcohol solvents]]

[[Category:Tertiary alcohols]]

[[Category:Oxygenates]]

[[Category:GABAA receptor positive allosteric modulators]]

[[Category:Glycine receptor agonists]]

[[Category:Sedatives]]

[[Category:Hypnotics]]

[[Category:Alkanols]]

[[Category:Tert-butyl compounds]]