Succinonitrile

{{Chembox

| Watchedfields = changed

| verifiedrevid = 470472165

| ImageFile = Succinonitrile.png

| ImageClass = skin-invert-image

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 150

| ImageName = Skeletal formula of succinonitrile

| ImageFileL1 = Succinonitrile-3D-balls.png

| ImageClassL1 = bg-transparent

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageSizeL1 = 120

| ImageNameL1 = Ball and stick model of succinonitrile

| ImageFileR1 = Succinonitrile-3D-spacefill.png

| ImageClassR1 = bg-transparent

| ImageFileR1_Ref = {{chemboximage|correct|??}}

| ImageNameR1 = Spacefill model of succinonitrile

| PIN = Butanedinitrile{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=902 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}

| OtherNames = {{Unbulleted list|Deprelin|Dicyanoethane|Ethylene cyanide

}}

|Section1={{Chembox Identifiers

| CASNo = 110-61-2

| CASNo_Ref = {{cascite|correct|CAS}}

| PubChem = 8062

| ChemSpiderID = 21106481

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| UNII = 1R479O92DO

| UNII_Ref = {{fdacite|correct|FDA}}

| EINECS = 203-783-9

| MeSHName = succinonitrile

| RTECS = WN3850000

| Beilstein = 1098380

| 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

| Density = 985 mg mL⁻¹

| MeltingPtC = 58

| MeltingPt_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}}

| BoilingPtK = 539.2

| Solubility = 130 g L⁻¹

| VaporPressure = 300 Pa (at 100 °C)

}}

|Section3={{Chembox Thermochemistry

| DeltaHf = 139.3–140.4 kJ mol⁻¹

| DeltaHc = −2.2848–−2.2860 MJ mol⁻¹

| Entropy = 191.59 J K⁻¹ mol⁻¹

| HeatCapacity = 145.60 J K⁻¹ mol⁻¹

}}

|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⁻¹ (oral, rat)

| PEL = none{{PGCH|0573}}

| IDLH = N.D.

| REL = TWA 6 ppm (20 mg/m³)

}}

|Section5={{Chembox Related

| OtherFunction_label = alkanenitriles

| OtherFunction = {{Unbulleted list|Propanenitrile|Aminopropionitrile|Pivalonitrile|Acetone cyanohydrin|Butyronitrile|Tetramethylsuccinonitrile}}

| OtherCompounds = DBNPA

}}

}}

Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C₂H₄(CN)₂. It is a colorless waxy solid which melts at 58 °C.

Succinonitrile is produced by the addition of hydrogen cyanide to acrylonitrile (hydrocyanation):{{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

}}

:CH₂=CHCN + HCN → NCCH₂CH₂CN

Hydrogenation of succinonitrile yields putrescine (1,4-diaminobutane).