tert -Butyl alcohol
Skeletal formula of tert -butyl alcohol
Ball and stick model of tert -butyl alcohol
Names
Preferred IUPAC name
Other names
t -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
74.123 g·mol−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]
log P
0.584
Vapor pressure
4.1 kPa (at 20 °C)
Acidity (pK a )
16.54 [ 3]
5.742× 10−5 cm3 /mol
1.387
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 labelling :
Danger
H225 , H319 , H332 , H335
P210 , P261 , P305+P351+P338
NFPA 704 (fire diamond)
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) 3500 mg/kg (rat, oral)[ 4]
NIOSH (US health exposure limits):
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 -Butanol
Isobutanol
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 alcohol is the simplest tertiary alcohol , with a formula of (CH3 )3 COH (sometimes represented as t -BuOH). Its isomers 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 .
tert -Butyl alcohol has been identified in beer and chickpeas .[ 5] It is also found in cassava ,[ 6] which is used as a fermentation ingredient in certain alcoholic beverages .
tert -Butyl alcohol is derived commercially from isobutane as a coproduct of propylene oxide production. It can also be produced by the catalytic 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 (K2 CO3 ), 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 Å molecular sieves , aluminium tert -butylate, calcium hydride (CaH2 ), or fractional crystallization under inert atmosphere.[ 7]
tert -Butyl alcohol is used as a solvent, ethanol denaturant , paint remover ingredient, and gasoline octane booster and oxygenate . It is a chemical intermediate used to produce methyl tert -butyl ether (MTBE) and ethyl tert -butyl ether (ETBE) by reaction with methanol and ethanol , respectively, and tert -butyl hydroperoxide (TBHP) by reaction with hydrogen 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 strong base to give the alkoxide . Particularly common is potassium tert -butoxide , which is prepared by treating tert -butanol with potassium metal.[ 8]
K + t -BuOH → t -BuO− K+ + 1 / 2 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 SN 2 reaction.
tert -Butyl alcohol reacts with hydrogen chloride to form tert -butyl chloride .
O-Chlorination of tert-butyl alcohol with hypochlorous acid to give tert-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] 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.
^ 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 . Retrieved 29 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. Retrieved 29 March 2018 .
^ "Archived copy" (PDF) . Archived from the original (PDF) on 2016-03-04. Retrieved 2013-03-05 .((cite web ))
: CS1 maint: archived copy as title (link )
^ Perrin, D. D.; Armarego, W. L. F. (1988). Purification of Laboratory Chemicals (3rd ed.). Pergamon Press. 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 .
By consumption
Primary alcohols (1°)
Methanol Ethanol Butanol Straight-chain saturated C1 — C9 Straight-chain saturated C10 — C19 Straight-chain saturated C20 — C29 Straight-chain saturated C30 — C39
1-Triacontanol (melissyl / myricyl)
1-Hentriacontanol
1-Dotriacontanol (lacceryl)
1-Tritriacontanol
1-Tetratriacontanol (geddyl)
1-Pentatriacontanol
1-Hexatriacontanol
1-Heptatriacontanol
1-Octatriacontanol
1-Nonatriacontanol
Straight-chain saturated C40 — C49
1-Tetracontanol
1-Hentetracontanol
1-Dotetracontanol
1-Tritetracontanol
1-Tetratetracontanol
1-Pentatetracontanol
1-Hexatetracontanol
1-Heptatetracontanol
1-Octatetracontanol
1-Nonatetracontanol
Secondary alcohols (2°) Tertiary alcohols (3°) Hydric alcohols
Amyl alcohols Aromatic alcohols Saturatedfatty alcohols Branched and unsaturatedfatty alcohols Sugar alcohols
C1 — C7 Deoxy sugar alcohols Cyclic sugar alcohols Glycylglycitols
Terpene alcohols
Monoterpene alcohols Sesquiterpene alcohols Diterpene alcohols
Dialcohols Trialcohols Sterols Fluoroalcohols Preparations Reactions
Alcohols Barbiturates Benzodiazepines Carbamates Flavonoids Imidazoles Kava constituents
10-Methoxyyangonin
11-Methoxyyangonin
11-Hydroxyyangonin
Desmethoxyyangonin
11-Methoxy-12-hydroxydehydrokavain
7,8-Dihydroyangonin
Kavain
5-Hydroxykavain
5,6-Dihydroyangonin
7,8-Dihydrokavain
5,6,7,8-Tetrahydroyangonin
5,6-Dehydromethysticin
Methysticin
7,8-Dihydromethysticin
Yangonin
Monoureides 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
Niacin
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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
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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
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Gaboxadol (THIP)
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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 and picrotoxinin )
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