| 词条 | Pentanenitrile |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | Reference = | ImageFile1 = Pentanenitrile.svg | IUPACName = | OtherNames = {{Unbulleted list|Valeronitrile|n-valeronitrile|1-Cyanobutane| }} |Section1={{Chembox Identifiers | CASNo = 110-59-8 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = | ChemSpiderID = 7770 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | EINECS = 203-781-8 | MeSHName = | ChEBI = | ChEBI_Ref = {{ebicite|changed|EBI}} | RTECS = | Beilstein = | ChEMBL = 1503158 | UNNumber = 3273 | UNII = X44H3R47D4 | SMILES = CCCCC#N | StdInChI = 1S/C5H9N/c1-2-3-4-5-6/h2-4H2,1H3 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = RFFFKMOABOFIDF-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} }} |Section2={{Chembox Properties | C=5 | H=9 | N=1 | Appearance = Colorless liquid | Odor = | Density = 0.8008 | MeltingPtC = -96.2 | BoilingPtK = 414 | VaporPressure = 5 mm Hg | CriticalT = 610.3 K | CriticalP = 35.80 bar | Solubility = insoluble | SolubleOther = soluble in benzene, acetone, ether | HenryConstant = | RefractIndex = 1.3949 | MagSus = | Dipole = }} |Section3={{Chembox Thermochemistry | DeltaHf = | DeltaHc = | HeatCapacity = }} |Section4={{Chembox Hazards | GHSPictograms = {{GHS02}} {{GHS skull and crossbones}}{{GHS07}} | GHSSignalWord = DANGER | HPhrases = {{H-phrases|226|301|302}} | PPhrases = {{P-phrases|210|233|240|241|242|243|264|270|280|301+310|301+312|303+361+353|321|330|370+378|403+235|405|501}} | NFPA-H = 3 | NFPA-F = 3 | NFPA-R = 0 | FlashPtC = 40 | AutoignitionPtC = | ExploLimits = | LD50 = 191 mg/kg fat[1] | PEL = | IDLH = | REL = }} |Section5={{Chembox Related | OtherFunction_label = alkanenitriles | OtherFunction = {{Unbulleted list|Isobutyronitrile|Propanenitrile|Malononitrile|Pivalonitrile|Succinonitrile|Glutaronitrile|Butyronitrile|Pivalonitrile}} | OtherCompounds = }} }} Pentanenitrile, valeronitrile or butyl cyanide is a nitrile with the formula C4H9CN. This can be written BuCN, with Bu representing n-butyl. ProductionPentanenitrile can be produced by heating 1-chlorobutane with sodium cyanide in dimethyl sulfoxide. This reaction takes about 20 minutes, keeping the temperature below 160 °C. The yield is about 93%.[1] Another way to get the substance is by heating butyraldehyde with hydroxylamine.[2] Pentanenitrile is contained in bone oil.[3] PropertiesThe pentanenitrile molecule is flexible and can adopt a number of different conformers, so that it will naturally be a mixture. These conformers are called anti-anti (30%), anti-gauche (46%), gauche-anti, gauche-gauche-cis, and gauche-gauche-trans.[4] BiologyPentanenitrile is toxic to animals, and produces its action by the liberation of cyanide by cytochrome P450. The cyanide is detoxifided and excreted in urine as thiocyanate.[5] Pentanenitrile is found in Brassica species and varieties such as broccoli. Pentanenitrile is hydrolyzed to valeric acid by the fungi Gibberella intermedia,[6] Fusarium oxysporum, and Aspergillus niger in which it induces production of the nitrilase enzyme.[7] References1. ^{{cite journal|last1=Smiley|first1=Robert|last2=Arnold|first2=Charles|title=Notes- Aliphatic Nitriles from Alkyl Chlorides|journal=The Journal of Organic Chemistry|date=February 1960|volume=25|issue=2|pages=257–258|doi=10.1021/jo01072a600}} 2. ^{{cite journal|title=Red mud catalyzed one-pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride under microwave irradiation|journal=Arkivoc|date=5 October 2007|volume=2007|issue=15|pages=162|doi=10.3998/ark.5550190.0008.f16}} 3. ^{{cite book|title=Toxic Substances Control Act (TSCA) Chemical Substance Inventory|date=1979|publisher=the Office|url=https://books.google.com.au/books?id=2psDsfJ3GtoC&pg=RA1-PA2|language=en}} 4. ^{{cite journal|last1=Crowder|first1=G.A.|title=Conformational analysis of n-butyl cyanide|journal=Journal of Molecular Structure: THEOCHEM|date=October 1989|volume=200|pages=235–244|doi=10.1016/0166-1280(89)85056-0}} 5. ^1 {{cite book|last1=Buhler|first1=D. R.|last2=Reed|first2=D. J.|title=Nitrogen and Phosphorus Solvents|date=2013|publisher=Elsevier|isbn=9781483290201|pages=359–362|url=https://books.google.com.au/books?id=uAQhBQAAQBAJ&pg=PA359|language=en}} 6. ^{{cite journal|last1=Gong|first1=Jin-Song|last2=Li|first2=Heng|last3=Zhu|first3=Xiao-Yan|last4=Lu|first4=Zhen-Ming|last5=Wu|first5=Yan|last6=Shi|first6=Jing-Song|last7=Xu|first7=Zheng-Hong|last8=Yun|first8=Sung-Hwan|title=Fungal His-Tagged Nitrilase from Gibberella intermedia: Gene Cloning, Heterologous Expression and Biochemical Properties|journal=PLoS ONE|date=30 November 2012|volume=7|issue=11|pages=e50622|doi=10.1371/journal.pone.0050622}}{{open access}} 7. ^{{cite journal|last1=Kaplan|first1=Ondřej|last2=Vejvoda|first2=Vojtěch|last3=Charvátová-Pišvejcová|first3=Andrea|last4=Martínková|first4=Ludmila|title=Hyperinduction of nitrilases in filamentous fungi|journal=Journal of Industrial Microbiology & Biotechnology|date=15 August 2006|volume=33|issue=11|pages=891–896|doi=10.1007/s10295-006-0161-9}} 1 : Nitriles |
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