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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
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
| Watchedfields = changed
{{chembox
| verifiedrevid = 444121536 | verifiedrevid = 470472165
| ImageFile = Succinonitrile.png | ImageFile = Succinonitrile.png
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 150 | ImageSize = 150
| ImageAlt = Skeletal formula | ImageName = Skeletal formula of succinonitrile
| ImageFile1 = Succinonitrile-3D-balls.png | ImageFileL1 = Succinonitrile-3D-balls.png
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageSize1 = 160
| ImageSizeL1 = 120
| ImageAlt1 = Ball-and-stick model
| ImageNameL1 = Ball and stick model of succinonitrile
| IUPACName = Butanedinitrile
| ImageFileR1 = Succinonitrile-3D-spacefill.png
| OtherNames = Dicyanoethane<br>Ethylene cyanide<br>Deprelin
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| Section1 = {{Chembox Identifiers
| ImageNameR1 = Spacefill model of succinonitrile
| InChI = 1/C4H4N2/c5-3-1-2-4-6/h1-2H2
| 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>
| InChIKey = IAHFWCOBPZCAEA-UHFFFAOYAW
| OtherNames = {{Unbulleted list|Deprelin|Dicyanoethane|Ethylene cyanide
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
}}
| StdInChI = 1S/C4H4N2/c5-3-1-2-4-6/h1-2H2
|Section1={{Chembox Identifiers
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IAHFWCOBPZCAEA-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 110-61-2 | CASNo = 110-61-2
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 8062
| PubChem = 8062
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=21106481 | ChemSpiderID = 21106481
| UNII_Ref = {{fdacite|correct|FDA}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = 1R479O92DO | UNII = 1R479O92DO
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 203-783-9
| MeSHName = succinonitrile
| RTECS = WN3850000
| Beilstein = 1098380
| SMILES = N#CCCC#N | SMILES = N#CCCC#N
| StdInChI = 1S/C4H4N2/c5-3-1-2-4-6/h1-2H2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IAHFWCOBPZCAEA-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C=4 | H=4 | N=2
| Appearance = Colorless, waxy crystals
| Odor = odorless<ref name=PGCH/>
| Density = 985 mg mL<sup>−1</sup>
| MeltingPtC = 58
| 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>
| BoilingPtK = 539.2
| Solubility = 130 g L<sup>−1</sup>
| VaporPressure = 300 Pa (at 100&nbsp;°C)
}}
|Section3={{Chembox Thermochemistry
| DeltaHf = 139.3–140.4 kJ mol<sup>−1</sup>
| DeltaHc = −2.2848–−2.2860 MJ mol<sup>−1</sup>
| Entropy = 191.59 J K<sup>−1</sup> mol<sup>−1</sup>
| HeatCapacity = 145.60 J K<sup>−1</sup> mol<sup>−1</sup>
}}
|Section4={{Chembox Hazards
| GHSPictograms = {{GHS exclamation mark}}
| GHSSignalWord = '''WARNING'''
| HPhrases = {{H-phrases|302|315|319|335}}
| PPhrases = {{P-phrases|261|305+351+338}}
| FlashPtC = 113
| LD50 = 450 mg kg<sup>−1</sup> <small>(oral, rat)</small>
| PEL = none<ref name=PGCH>{{PGCH|0573}}</ref>
| IDLH = N.D.<ref name=PGCH/>
| REL = TWA 6 ppm (20 mg/m<sup>3</sup>)<ref name=PGCH/>
}}
|Section5={{Chembox Related
| OtherFunction_label = alkanenitriles
| OtherFunction = {{Unbulleted list|]|]|]|]|]|]}}
| OtherCompounds = ]
}} }}
| Section2 = {{Chembox Properties
| Formula = C<sub>4</sub>H<sub>4</sub>N<sub>2</sub>
| MolarMass = 80.09 g/mol
| Appearance = Colorless wax
| Density = 0.985 g/mL
| MeltingPt = 57 °C
| BoilingPt = 265-267 °C
| Solubility =
}}
| Section3 = {{Chembox Hazards
| FlashPt = 141 °C
| MainHazards = flammable
| Autoignition =
}}
}} }}
'''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&nbsp;°C.

Succinonitrile is produced by the addition of ] to ] (]):<ref>{{cite encyclopedia
| encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry
| title = Nitriles
| url = http://www.mrw.interscience.wiley.com/emrw/9783527306732/ueic/article/a17_363/current/html?hd=All%2Csuccinonitrile
| access-date = 2007-09-10
| edition = 7th
}}</ref>
:CH<sub>2</sub>=CHCN + HCN → NCCH<sub>2</sub>CH<sub>2</sub>CN

] of succinonitrile yields ] (1,4-diaminobutane).

==See also==
* ] - A di-nitrile with 3 carbon atoms
* ] - A di-nitrile with 5 carbon atoms
* ] - A di-nitrile with 6 carbon atoms

==References==
{{Reflist}}

==External links==
*
*

]


{{Organic-compound-stub}}