Revision as of 18:06, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 466517987 of page Succinonitrile for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 16:26, 18 August 2022 edit JWBE (talk | contribs)Extended confirmed users10,127 edits removed Category:Nitriles; added Category:Alkanedinitriles using HotCat |
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{{Chembox |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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| Watchedfields = changed |
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{{chembox |
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| verifiedrevid = 444121536 |
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| verifiedrevid = 470472165 |
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| ImageFile = Succinonitrile.png |
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| ImageFile = Succinonitrile.png |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageSize = 150 |
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| ImageSize = 150 |
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| ImageAlt = Skeletal formula |
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| ImageName = Skeletal formula of succinonitrile |
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| ImageFile1 = Succinonitrile-3D-balls.png |
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| ImageFileL1 = Succinonitrile-3D-balls.png |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageSize1 = 160 |
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| ImageSizeL1 = 120 |
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| ImageAlt1 = Ball-and-stick model |
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| ImageNameL1 = Ball and stick model of succinonitrile |
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| IUPACName = Butanedinitrile |
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| ImageFileR1 = Succinonitrile-3D-spacefill.png |
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| OtherNames = Dicyanoethane<br>Ethylene cyanide<br>Deprelin |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| Section1 = {{Chembox Identifiers |
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| ImageNameR1 = Spacefill model of succinonitrile |
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| InChI = 1/C4H4N2/c5-3-1-2-4-6/h1-2H2 |
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| PIN = Butanedinitrile<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=902 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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| InChIKey = IAHFWCOBPZCAEA-UHFFFAOYAW |
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| OtherNames = {{Unbulleted list|Deprelin|Dicyanoethane|Ethylene cyanide |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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| StdInChI = 1S/C4H4N2/c5-3-1-2-4-6/h1-2H2 |
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|Section1={{Chembox Identifiers |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = IAHFWCOBPZCAEA-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 110-61-2 |
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| CASNo = 110-61-2 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 8062 |
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| PubChem = 8062 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID=21106481 |
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| ChemSpiderID = 21106481 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII = 1R479O92DO |
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| UNII = 1R479O92DO |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 203-783-9 |
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| MeSHName = succinonitrile |
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| RTECS = WN3850000 |
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| Beilstein = 1098380 |
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| SMILES = N#CCCC#N |
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| SMILES = N#CCCC#N |
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| StdInChI = 1S/C4H4N2/c5-3-1-2-4-6/h1-2H2 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = IAHFWCOBPZCAEA-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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|Section2={{Chembox Properties |
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| C=4 | H=4 | N=2 |
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| Appearance = Colorless, waxy crystals |
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| Odor = odorless<ref name=PGCH/> |
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| Density = 985 mg mL<sup>−1</sup> |
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| MeltingPtC = 58 |
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| MeltingPt_ref = <ref>{{Cite journal|last1=Rubinstein|first1=E. R.|last2=Tirmizi|first2=S. H.|last3=Glicksman|first3=M. E.|date=1990-11-01|title=Long-term purity assessment in succinonitrile|url=https://dx.doi.org/10.1016%2F0022-0248%2890%2990290-2|journal=Journal of Crystal Growth|language=en|volume=106|issue=1|pages=89–96|doi=10.1016/0022-0248(90)90290-2|bibcode=1990JCrGr.106...89R|issn=0022-0248}}</ref> |
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| BoilingPtK = 539.2 |
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| Solubility = 130 g L<sup>−1</sup> |
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| VaporPressure = 300 Pa (at 100 °C) |
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}} |
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|Section3={{Chembox Thermochemistry |
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| DeltaHf = 139.3–140.4 kJ mol<sup>−1</sup> |
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| DeltaHc = −2.2848–−2.2860 MJ mol<sup>−1</sup> |
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| Entropy = 191.59 J K<sup>−1</sup> mol<sup>−1</sup> |
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| HeatCapacity = 145.60 J K<sup>−1</sup> mol<sup>−1</sup> |
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}} |
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|Section4={{Chembox Hazards |
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| GHSPictograms = {{GHS exclamation mark}} |
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| GHSSignalWord = '''WARNING''' |
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| HPhrases = {{H-phrases|302|315|319|335}} |
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| PPhrases = {{P-phrases|261|305+351+338}} |
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| FlashPtC = 113 |
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| LD50 = 450 mg kg<sup>−1</sup> <small>(oral, rat)</small> |
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| PEL = none<ref name=PGCH>{{PGCH|0573}}</ref> |
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| IDLH = N.D.<ref name=PGCH/> |
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| REL = TWA 6 ppm (20 mg/m<sup>3</sup>)<ref name=PGCH/> |
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}} |
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|Section5={{Chembox Related |
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| OtherFunction_label = alkanenitriles |
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| OtherFunction = {{Unbulleted list|]|]|]|]|]|]}} |
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| OtherCompounds = ] |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>4</sub>H<sub>4</sub>N<sub>2</sub> |
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| MolarMass = 80.09 g/mol |
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| Appearance = Colorless wax |
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| Density = 0.985 g/mL |
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| MeltingPt = 57 °C |
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| BoilingPt = 265-267 °C |
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| Solubility = |
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}} |
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| Section3 = {{Chembox Hazards |
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| FlashPt = 141 °C |
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| MainHazards = flammable |
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| Autoignition = |
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}} |
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}} |
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}} |
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'''Succinonitrile''', also '''butanedinitrile''', is a ], with the ] of C<sub>2</sub>H<sub>4</sub>(CN)<sub>2</sub>. It is a colorless waxy solid which melts at 58 °C. |
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Succinonitrile is produced by the addition of ] to ] (]):<ref>{{cite encyclopedia |
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| encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry |
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| title = Nitriles |
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| url = http://www.mrw.interscience.wiley.com/emrw/9783527306732/ueic/article/a17_363/current/html?hd=All%2Csuccinonitrile |
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| access-date = 2007-09-10 |
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| edition = 7th |
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}}</ref> |
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:CH<sub>2</sub>=CHCN + HCN → NCCH<sub>2</sub>CH<sub>2</sub>CN |
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] of succinonitrile yields ] (1,4-diaminobutane). |
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==See also== |
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* ] - A di-nitrile with 3 carbon atoms |
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* ] - A di-nitrile with 5 carbon atoms |
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* ] - A di-nitrile with 6 carbon atoms |
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==References== |
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{{Reflist}} |
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==External links== |
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* |
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* |
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] |
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{{Organic-compound-stub}} |