tert -Butyl alcoholSkeletal formula oftert -butyl alcohol Ball and stick model oftert -butyl alcohol
Sample of partially crystallizedtert -butyl alcohol Names Preferred IUPAC name Other namest -Butyl alcoholtert -Butanolt -Butanolt -BuOHTrimethyl carbinol[ 1] Tertiary butanol 2-Methyl-2-propanol 2M2P Identifiers 906698 ChEBI ChEMBL ChemSpider DrugBank ECHA InfoCard 100.000.809 EC Number 1833 MeSH tert-Butyl+Alcohol RTECS number UNII UN number 1120 InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3
Y Key: DKGAVHZHDRPRBM-UHFFFAOYSA-N
Y Properties C 4 H 10 O Molar mass −1 Appearance Colorless solid Odor Camphorous Density 0.775 g/mL Melting point 25 to 26 °C; 77 to 79 °F; 298 to 299 K Boiling point 82 to 83 °C; 179 to 181 °F; 355 to 356 K miscible[ 2] logP 0.584 Vapor pressure 4.1 kPa (at 20 °C) Acidity (pK a )16.54[ 3] × 10−5 cm3 /mol1.387 1.31 D Thermochemistry 215.37 J K−1 mol−1 189.5 J K−1 mol−1 −360.04 to −358.36 kJ mol−1 −2.64479 to −2.64321 MJ mol−1 Hazards GHS labellingDanger H225, H319, H332, H335 P210, P261, P305+P351+P338 NFPA 704 Flash point 11 °C (52 °F; 284 K) 480 °C (896 °F; 753 K) Explosive limits 2.4–8.0% Lethal dose or concentration (LD, LC):3559 mg/kg (rabbit, oral)[ 4] NIOSH TWA 100 ppm (300 mg/m3 )[ 1] TWA 100 ppm (300 mg/m3 ) ST 150 ppm (450 mg/m3 )[ 1] 1600 ppm[ 1] Safety data sheet (SDS)inchem.org Related compounds 2-Butanol n -ButanolIsobutanol
Related compounds
2-Methyl-2-butanol Trimethylsilanol Nonafluoro-tert-butyl alcohol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
tert -Butyl alcoholtertiary alcohol , with aformula of (CH3 )3 COH (sometimesrepresented ast -BuOH). Itsisomers are1-butanol ,isobutanol , andbutan-2-ol .tert -Butyl alcohol is a colorless solid, which melts near room temperature and has acamphor -like odor. It is miscible withwater ,ethanol anddiethyl ether .
tert -Butyl alcohol has been identified inbeer andchickpeas .[ 5] cassava ,[ 6] alcoholic beverages .
tert -Butyl alcohol is derived commercially fromisobutane as a coproduct ofpropylene oxide production. It can also be produced by the catalytichydration ofisobutylene , or by aGrignard reaction betweenacetone andmethylmagnesium chloride .
Purification cannot be performed by simple distillation due to formation of anazeotrope 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 withcalcium oxide (CaO),potassium carbonate (K2 CO3 ),calcium sulfate (CaSO4 ), ormagnesium sulfate (MgSO4 ), followed by fractional distillation. Anhydroustert -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 Å molecular sieves ,aluminiumtert -butylate ,calcium hydride (CaH2 ), or fractional crystallization under inert atmosphere.[ 7]
tert -Butyl alcohol is used as a solvent, ethanoldenaturant ,paint remover ingredient, andgasoline octane booster andoxygenate . It is a chemical intermediate used to producemethyltert -butyl ether (MTBE) andethyltert -butyl ether (ETBE) by reaction withmethanol andethanol , respectively, andtert -butyl hydroperoxidehydrogen peroxide .
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 strongbase to give thealkoxide . Particularly common ispotassiumtert -butoxide , which is prepared by treatingtert -butanol withpotassium metal.[ 8]
K +t -BuOH →t -BuO− K+ +1 / 2 H2 Thetert -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 innucleophilic substitution , such as in aWilliamson ether synthesis or anSN 2 reaction.
tert -Butyl alcohol reacts withhydrogen chloride to formtert -butyl chloride
O-Chlorination of tert-butyl alcohol with hypochlorous acid to givetert-butyl hypochlorite :[ 9]
(CH3 )3 COH + HOCl → (CH3 )3 COCl + H2 O Pharmacology and toxicology [ edit ] There is limited data on the pharmacology and toxicology of tert-butanol in humans and other animals.[ 10]
^a b c d NIOSH Pocket Guide to Chemical Hazards."#0078" .National Institute for Occupational Safety and Health (NIOSH). ^ "ICSC 0114 –tert -Butanol" .Inchem.org . Retrieved29 March 2018 .^ Reeve, W.; Erikson, C. M.; Aluotto, P. F. (1979)."tert-Butyl alcohol" .Can. J. Chem .57 : 2747.doi :10.1139/v79-444 ^ "tert-Butyl alcohol" .Immediately Dangerous to Life or Health Concentrations (IDLH) .National Institute for Occupational Safety and Health (NIOSH).^ "t -Butyl Alcohol" .National Library of Medicine HSDB Database . National Institute for Health. Retrieved29 March 2018 .^ "Archived copy" (PDF) . Archived fromthe original (PDF) on 2016-03-04. Retrieved2013-03-05 .{{cite web }}: CS1 maint: archived copy as title (link )^ Perrin, D. D.; Armarego, W. L. F. (1988).Purification of Laboratory Chemicals ISBN 9780080347141 ^ Johnson, W. S.; Schneider, W. P. (1950). "β-Carbethoxy-γ,γ-diphenylvinylacetic acid".Organic Syntheses 30 : 18.doi :10.15227/orgsyn.030.0018 ^ Mintz, H. M.; Walling, C. (1969). "t-Butyl Hypochlorite".Org. Synth .49 : 9.doi :10.15227/orgsyn.049.0009 . ^ Douglas McGregor (2010). "Tertiary-Butanol: a toxicological review".Critical Reviews in Toxicology 40 (8):697– 727.doi :10.3109/10408444.2010.494249 .PMID 20722584 .S2CID 26041562 .
Alcohols Barbiturates Benzodiazepines Carbamates Flavonoids Imidazoles Kava constituentsMonoureides Neuroactive steroids Nonbenzodiazepines Phenols Piperidinediones Pyrazolopyridines Quinazolinones Volatiles /gases Others/unsorted 3-Hydroxybutanal α-EMTBL AA-29504 Alogabat Avermectins (e.g.,ivermectin )Bromide compounds (e.g.,lithium bromide ,potassium bromide ,sodium bromide )Carbamazepine Chloralose Chlormezanone Clomethiazole Darigabat DEABL Deuterated etifoxine Dihydroergolines (e.g.,dihydroergocryptine ,dihydroergosine ,dihydroergotamine ,ergoloid (dihydroergotoxine) )DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g.,flufenamic acid ,mefenamic acid ,niflumic acid ,tolfenamic acid )Fluoxetine Flupirtine Hopantenic acid KRM-II-81 Lanthanum Lavender oil Lignans (e.g.,4-O-methylhonokiol ,honokiol ,magnolol ,obovatol )Loreclezole Menthyl isovalerate (validolum) Monastrol Nicotinic acid Nicotinamide Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g.,sulfonmethane (sulfonal) ,tetronal ,trional )Terpenoids (e.g.,borneol )Topiramate Valerian constituents (e.g.,isovaleric acid ,isovaleramide ,valerenic acid ,valerenol )
Receptor (ligands )
GlyR Tooltip Glycine receptor Positive modulators: Alcohols (e.g.,brometone ,chlorobutanol (chloretone) ,ethanol (alcohol) ,tert -butanol (2M2P)tribromoethanol ,trichloroethanol ,trifluoroethanol )Alkylbenzene sulfonate Anandamide Barbiturates (e.g.,pentobarbital ,sodium thiopental )Chlormethiazole D12-116 Dihydropyridines (e.g.,nicardipine )Etomidate Ginseng constituents (e.g.,ginsenosides (e.g.,ginsenoside-Rf ))Glutamic acid (glutamate) Ivermectin Ketamine Neuroactive steroids (e.g.,alfaxolone ,pregnenolone (eltanolone) ,pregnenolone acetate ,minaxolone ,ORG-20599 )Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines (e.g.,atropine ,bemesetron ,cocaine ,LY-278584 ,tropisetron ,zatosetron )Volatiles /gases (e.g.,chloral hydrate ,chloroform ,desflurane ,diethyl ether (ether) ,enflurane ,halothane ,isoflurane ,methoxyflurane ,sevoflurane ,toluene ,trichloroethane (methyl chloroform) ,trichloroethylene )Xenon Zinc Antagonists: 2-Aminostrychnine 2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine Diaboline Endocannabinoids (e.g.,2-AG ,anandamide (AEA) )Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline N-Methylstrychnine N,N-Dimethylmuscimol Nipecotic acid Pitrazepin Pseudostrychnine Quinolines (e.g.,4-hydroxyquinoline ,4-hydroxyquinoline-3-carboxylic acid ,5,7-CIQA ,7-CIQ ,7-TFQ ,7-TFQA )RU-5135 Sinomenine Strychnine Thiocolchicoside Tutin Negative modulators: Amiloride Benzodiazepines (e.g.,bromazepam ,clonazepam ,diazepam ,flunitrazepam ,flurazepam )Corymine Cyanotriphenylborate Daidzein Dihydropyridines (e.g.,nicardipine ,nifedipine ,nitrendipine )Furosemide Genistein Ginkgo constituents (e.g.,bilobalide ,ginkgolides (e.g.,ginkgolide A ,ginkgolide B ,ginkgolide C ,ginkgolide J ,ginkgolide M ))Imipramine NBQX Neuroactive steroids (e.g.,3α-androsterone sulfate ,3β-androsterone sulfate ,deoxycorticosterone ,DHEA sulfate ,pregnenolone sulfate ,progesterone )Opioids (e.g.,codeine ,dextromethorphan ,dextrorphan ,levomethadone ,levorphanol ,morphine ,oripavine ,pethidine ,thebaine )Picrotoxin (i.e.,picrotin andpicrotoxinin )PMBA Riluzole Tropeines (e.g.,bemesetron ,LY-278584 ,tropisetron ,zatosetron )Verapamil Zinc NMDAR Tooltip N-Methyl-D-aspartate receptor
Transporter (blockers )
GlyT1 Tooltip Glycine transporter 1 GlyT2 Tooltip Glycine transporter 2
