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enu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 history and occurrence 2 production toggle production subsection 2 1 laboratory synthesis 2 2 biosynthesis of isobutanol 3 applications 4 safety and regulation 5 references 6 external links toggle the table of contents isobutanol 33 languages العربية تۆرکجه bosanski čeština deutsch esperanto español euskara فارسی suomi français galego עברית magyar bahasa indonesia italiano 日本語 한국어 македонски bahasa melayu nederlands norsk bokmål polski português română русский srpskohrvatski српскохрватски српски srpski svenska türkçe українська اردو 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical compound ch3 2chch2oh isobutanol 2 methyl propan 1 ol skeletal formula of isobutanol ball and stick model of isobutanol names preferred iupac name 2 methylpropan 1 ol other names isobutyl alcohol isobutanol 2 methyl 1 propanol 2 methylpropyl alcohol isopropylcarbinol identifiers cas number 78 83 1 y 3d model jsmol interactive image abbreviations iba i buoh i buoh i buoh beilstein reference 1730878 chebi chebi 46645 y chembl chembl269630 y chemspider 6312 y echa infocard 100 001 044 ec number 201 148 0 gmelin reference 49282 kegg c14710 y pubchem cid 6560 rtecs number np9625000 unii 56f9z98tem y un number 1212 comptox dashboard epa dtxsid0021759 inchi inchi 1s c4h10o c1 4 2 3 5 h4 5h 3h2 1 2h3 y key zxekiibdnhejcq uhfffaoysa n y inchi 1 c4h10o c1 4 2 3 5 h4 5h 3h2 1 2h3 smiles cc c co properties 1 chemical formula c 4 h 10 o molar mass 74 123 g mol 1 appearance colorless liquid odor sweet musty 2 density 0 802 g cm 3 liquid melting point 108 c 162 f 165 k boiling point 107 89 c 226 20 f 381 04 k solubility in water 8 7 ml 100 ml citation needed log p 0 8 vapor pressure 9 mmhg 20 c 2 refractive index n d 1 3959 viscosity 3 95 cp at 20 c hazards 1 ghs labelling pictograms signal word danger hazard statements h226 h315 h318 h335 h336 precautionary statements p210 p233 p240 p241 p242 p243 p261 p264 p271 p280 p302 p352 p303 p361 p353 p304 p340 p305 p351 p338 p310 p312 p321 p332 p313 p362 p370 p378 p403 p233 p403 p235 p405 p501 nfpa 704 fire diamond 1 3 0 flash point 28 c 82 f 301 k autoignition temperature 415 c 779 f 688 k explosive limits 1 7 10 9 lethal dose or concentration ld lc ld lo lowest published 3750 mg kg rabbit oral 2460 mg kg rat oral 3 niosh us health exposure limits pel permissible twa 100 ppm 300 mg m 3 2 rel recommended twa 50 ppm 150 mg m 3 2 idlh immediate danger 1600 ppm 2 safety data sheet sds icsc 0113 related compounds related butanols 1 butanol sec butanol tert butanol related compounds isobutyraldehyde isobutyric acid except where otherwise noted data are given for materials in their standard state at 25 c 77 f 100 kpa y verify what is y n infobox references chemical compound isobutanol iupac nomenclature 2 methylpropan 1 ol is an organic compound with the formula ch 3 2 chch 2 oh sometimes represented as i buoh this colorless flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters its isomers are 1 butanol 2 butanol and tert butanol all of which are important industrially 4 history and occurrence edit fusel alcohols including isobutanol are grain fermentation byproducts therefore trace amounts of isobutanol may be present in many alcoholic beverages in 1852 charles adolphe wurtz subjected such alcohols to fractional distillation and identified in some of them a butylic alcohol boiling at around 108 c 5 its structure was initially unclear with some chemists believing it corresponded to butyric acid but theoretical considerations indicated that normal butanol should have a higher boiling point and in 1867 emil erlenmeyer and independently vladimir markovnikov determined its actual structure by proving its oxidation product to be isobutyric acid 6 7 production edit isobutanol is produced by the carbonylation of propylene two methods are practiced industrially hydroformylation is more common and generates a mixture of isobutyraldehyde and butyraldehyde ch 3 ch ch 2 co h 2 ch 3 ch 2 ch 2 cho the reaction is catalyzed by cobalt or rhodium complexes the resulting aldehydes are hydrogenated to the alcohols which are then separated in reppe carbonylation the same products are obtained but the hydrogenation is effected by the water gas shift reaction 4 laboratory synthesis edit propanol and methanol can be reacted to produce isobutyl alcohol via guerbet condensation 8 biosynthesis of isobutanol edit main article butanol fuel e coli as well as several other organisms has been genetically modified to produce c4 alcohols from glucose including isobutanol 1 butanol 2 methyl 1 butanol 3 methyl 1 butanol and 2 phenylethanol the host s highly active amino acid biosynthetic pathway is shifted to alcohol production α ketoisovalerate derived from valine is prone to decarboxylation to give isobutyraldehyde which is susceptible to reduction to the alcohol 9 ch 3 2 chc o co 2 h ch 3 2 chcho co 2 ch 3 2 chcho nadh h ch 3 2 chch 2 oh nad applications edit the uses of isobutanol and 1 butanol are similar they are often used interchangeably the main applications are as varnishes and precursors to esters which are useful solvents e g isobutyl acetate isobutyl esters of phthalic adipic and related dicarboxylic acids are common plasticizers 4 isobutanol is also a component of some biofuels 10 safety and regulation edit isobutanol is one of the least toxic of the butanols with an ld 50 of 2460 mg kg rat oral 4 in march 2009 the government of canada announced a ban on isobutanol use in cosmetics 11 references edit 1 2 isobutanol international chemical safety card 0113 geneva international programme on chemical safety april 2005 1 2 3 4 5 niosh pocket guide to chemical hazards 0352 national institute for occupational safety and health niosh isobutyl alcohol immediately dangerous to life or health concentrations national institute for occupational safety and health 1 2 3 4 hahn heinz dieter dämbkes georg rupprich norbert 2005 butanols ullmann s encyclopedia of industrial chemistry weinheim wiley vch doi 10 1002 14356007 a04_463 isbn 978 3 527 30673 2 s fr page comptes rendus hebdomadaires des séances de l académie des sciences tome 035 1852 djvu 314 roscoe henry enfield schorlemmer carl 1888 the chemistry of the hydrocarbons and their derivatives or organic chemistry 1882 1892 6 v d appleton the quiet revolution carlini carlo flego cristina marchionna mario 2004 09 01 guerbet condensation of methanol with n propanol to isobutyl alcohol over heterogeneous copper chromite mg al mixed oxides catalysts molecular catalysis 220 2 215 220 doi 10 1016 j molcata 2004 05 034 the synthesis of isobutyl alcohol from methanol meoh and n propanol proh through the guerbet condensation has been studied using catalytic system of copper chromite and mg al mixed oxides atsumi shota hanai taizo liao james c january 2008 non fermentative pathways for synthesis of branched chain higher alcohols as biofuels nature 451 7174 86 89 bibcode 2008natur 451 86a doi 10 1038 nature06450 pmid 18172501 s2cid 4413113 peralta yahya pamela p zhang fuzhong del cardayre stephen b keasling jay d 15 august 2012 microbial engineering for the production of advanced biofuels nature 488 7411 320 328 bibcode 2012natur 488 320p doi 10 1038 nature11478 pmid 22895337 s2cid 4423203 cosmetic chemicals banned in canada chem eng news 87 11 38 2009 03 16 external links edit wikimedia commons has media related to isobutanol international chemical safety card 0113 niosh pocket guide to chemical hazards 0352 national institute for occupational safety and health niosh ipcs environmental health criteria 65 butanols four isomers ipcs health and safety guide 9 isobutanol v t e alcohols by consumption alcohols found in alcoholic drinks 1 propanol 2 methyl 1 butanol ethanol isoamyl alcohol isobutanol phenethyl alcohol tert amyl alcohol tert butyl alcohol tryptophol medical alcohol ethchlorvynol methylpentynol methanol poisoning ethanol toxic alcohols isopropyl alcohol methanol primary alcohols 1 methanol 4 methylcyclohexanemethanol aminomethanol cyclohexylmethanol methoxymethanol methylazoxymethanol trifluoromethanol ethanol 1 aminoethanol 2 2 2 trichloroethanol 2 2 2 trifluoroethanol 2 2 ethoxyethoxy ethanol 2 2 methoxyethoxy ethanol 2 2 methoxyethoxy ethanol 2 butoxyethanol 2 chloroethanol 2 ethoxyethanol 2 fluoroethanol 2 mercaptoethanol 2 methoxyethanol aminoethylethanolamine diethylethanolamine dimethylethanolamine ethanol ethanolamine n n diisopropylaminoethanol n methylethanolamine phenoxyethanol tribromoethanol butanol 2 methyl 1 butanol isobutanol n butanol straight chain saturated c 1 c 9 methanol ethanol 1 propanol 1 butanol 1 pentanol 1 hexanol 1 heptanol 1 octanol capryl 1 nonanol pelargonic straight chain saturated c 10 c 19 1 decanol capric 1 undecanol hendecyl 1 dodecanol lauryl 1 tridecanol 1 tetradecanol myristyl 1 pentadecanol 1 hexadecanol cetyl palmityl 1 heptadecanol 1 octadecanol stearyl 1 nonadecanol straight chain saturated c 20 c 29 1 icosanol arachidyl 1 heneicosanol 1 docosanol behenyl 1 tricosanol 1 tetracosanol lignoceryl 1 pentacosanol 1 hexacosanol ceryl 1 heptacosanol 1 octacosanol cluytyl montanyl 1 nonacosanol straight chain saturated c 30 c 39 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 c 40 c 49 1 tetracontanol 1 hentetracontanol 1 dotetracontanol 1 tritetracontanol 1 tetratetracontanol 1 pentatetracontanol 1 hexatetracontanol 1 heptatetracontanol 1 octatetracontanol 1 nonatetracontanol 2 ethylhexanol allyl alcohol anisyl alcohol benzyl alcohol cinnamyl alcohol crotyl alcohol furfuryl alcohol isoamyl alcohol neopentyl alcohol nicotinyl alcohol perillyl alcohol phenethyl alcohol prenol propargyl alcohol salicyl alcohol tryptophol vanillyl alcohol veratrole alcohol secondary alcohols 2 1 phenylethanol 2 butanol 2 deoxyerythritol 2 heptanol 3 heptanol 2 hexanol 3 hexanol 3 methyl 2 butanol 2 nonanol 2 octanol 2 pentanol 3 pentanol cyclohexanol cyclopentanol cyclopropanol diphenylmethanol isopropanol pinacolyl alcohol pirkle s alcohol propylene glycol methyl ether tertiary alcohols 3 2 methyl 2 pentanol 2 methylheptan 2 ol 2 methylhexan 2 ol 3 methyl 3 pentanol 3 methyloctan 3 ol diacetone alcohol ethchlorvynol methylpentynol nonafluoro tert butyl alcohol tert amyl alcohol tert butyl alcohol triphenylethanol triphenylmethanol hydric alcohols monohydric alcohols methanol c 1 ethanol c 2 isopropanol c 3 1 butanol c 4 1 pentanol c 5 cetyl alcohol c 16 dihydric alcohols ethylene glycol propylene glycol trihydric alcohols glycerol polyhydric alcohols sugar alcohols pentaerythritol ethylene glycol c 2 glycerol propylene glycol c 3 erythritol threitol c 4 xylitol c 5 mannitol sorbitol c 6 volemitol c 7 amyl alcohols 2 2 dimethylpropan 1 ol 2 methylbutan 1 ol 2 methylbutan 2 ol 3 methylbutan 1 ol 3 methylbutan 2 ol pentan 1 ol pentan 2 ol pentan 3 ol aromatic alcohols benzyl alcohol 2 4 dichlorobenzyl alcohol 3 nitrobenzyl alcohol saturated fatty alcohols cetostearyl alcohol decanol lauryl alcohol myristyl alcohol nonanol octanol tridecanol undecanol branched and unsaturated fatty alcohols 3 methyl 3 pentanol erucyl alcohol linolenyl alcohol linoleyl alcohol oleyl alcohol palmitoleyl alcohol tert amyl alcohol tert butyl alcohol sugar alcohols c 1 c 7 methylene glycol c 1 ethylene glycol c 2 glycerol c 3 erythritol c 4 threitol c 4 arabitol c 5 ribitol c 5 xylitol c 5 mannitol c 6 sorbitol c 6 galactitol c 6 iditol c 6 volemitol c 7 deoxy sugar alcohols fucitol cyclic sugar alcohols inositol glycylglycitols maltitol lactitol isomalt maltotriitol maltotetraitol polyglycitol terpene alcohols monoterpene alcohols borneol citronellol geraniol linalool menthol nerol rhodinol terpineol sesquiterpene alcohols bisabolol farnesol nerolidol patchoulol diterpene alcohols phytol dialcohols 1 3 butanediol 1 4 butanediol 1 5 pentanediol 2 methyl 2 propyl 1 3 propanediol diethylpropanediol ethylene glycol trialcohols glycerol sterols cholesterol ergosterol lanosterol β sitosterol stigmasterol fluoroalcohols 1 3 difluoro 2 propanol 2 2 2 trifluoroethanol 2 fluoroethanol nonafluoro tert butyl alcohol trifluoromethanol preparations substitution of haloalkane carbonyl reduction ether cleavage hydrolysis of epoxide hydration of alkene ziegler process reactions deprotonation protonation alcohol oxidation glycol cleavage nucleophilic substitution fischer speier esterification williamson ether synthesis elimination reaction nucleophilic substitution of carbonyl group friedel crafts alkylation nucleophilic conjugate addition transesterification category v t e hypnotics sedatives n05c gaba a alcohols 2m2b chloralodol ethanol alcohol diethylpropanediol ethchlorvynol methylpentynol trichloroethanol barbiturates allobarbital amobarbital aprobarbital barbital butabarbital butobarbital cyclobarbital ethallobarbital heptabarb hexobarbital mephobarbital methohexital narcobarbital pentobarbital phenallymal phenobarbital propylbarbital proxibarbal reposal secobarbital talbutal thiamylal thiopental thiotetrabarbital vinbarbital vinylbital benzodiazepines brotizolam cinolazepam climazolam clobazam clonazolam doxefazepam estazolam flubromazolam flunitrazolam flunitrazepam flurazepam flutemazepam flutoprazepam loprazolam lormetazepam midazolam nimetazepam nitemazepam nitrazepam nitrazolam quazepam temazepam triazolam carbamates carisoprodol emylcamate ethinamate hexapropymate meprobamate methocarbamol phenprobamate procymate tybamate imidazoles etomidate metomidate propoxate monoureides acecarbromal apronal apronalide bromisoval capuride carbromal ectylurea neurosteroids acebrochol alfadolone alfaxolone brexanolone allopregnanolone eltanolone pregnanolone ganaxolone hydroxydione minaxolone progesterone renanolone zuranolone nonbenzodiazepines eszopiclone indiplon lirequinil necopidem pagoclone pazinaclone saripidem suproclone suriclone zaleplon zolpidem zopiclone phenols cipepofol ciprofol fospropofol propofol propofol hemisuccinate piperidinediones glutethimide methyprylon piperidione pyrithyldione quinazolinones afloqualone cloroqualone diproqualone etaqualo...