Nicotinonitrile

{{Chembox

|ImageFile = 3-Cyanpyridin Strukturformel.svg

|PIN = Pyridine-3-carbonitrile

|Section1 = {{Chembox Identifiers

| PubChem = 79

| CASNo = 100-54-9

| EC_number = 202-863-0

| ChEBI = 86556

| ChEMBL = 3181972

| UNII = X64V0K6260

| ChemSpiderID = 78

| StdInChI=1S/C6H4N2/c7-4-6-2-1-3-8-5-6/h1-3,5H

| StdInChIKey = GZPHSAQLYPIAIN-UHFFFAOYSA-N

| SMILES = C1=CC(=CN=C1)C#N

}}

|Section2 = {{Chembox Properties

|C=6|H=4|N=2

|MeltingPtC=51

|BoilingPtC=206.9

|Density=1.1590

|VaporPressure = 0.296 mm Hg

}}

|Section3 = {{Chembox Structure

| Structure_ref ={{cite journal |last1=Kubiak |first1=R. |last2=Janczak |first2=J. |last3=Śledź |first3=M. |title=Crystal structures of 2- and 3-cyanopyridine |journal=Journal of Molecular Structure |date=June 2002 |volume=610 |issue=1–3 |pages=59–64 |doi=10.1016/S0022-2860(02)00012-1|bibcode=2002JMoSt.610...59K }}

|SpaceGroup=P2₁/c (No. 14)

|CrystalStruct =Monoclinic

|LattConst_a= 3.808 Å

|LattConst_b=13.120 Å

|LattConst_c=10.591 Å

|LattConst_beta= 97.97

|UnitCellVolume=524

|UnitCellFormulas=4

}}

|Section7={{Chembox Hazards

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|302|315|319|335}}

| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}}

}}

}}

Nicotinonitrile or 3-cyanopyridine is an organic compound with the formula NCC₅H₄N. The molecule consists of a pyridine ring with a nitrile group attached to the 3-position. A colorless solid, it is produced by ammoxidation of 3-methylpyridine:{{Ullmann|last1=Abe|first1=Nobuyuki|last2=Ichimura|first2=Hisao|last3=Kataoka|first3=Toshiaki|last4=Morishita|first4=Sinji|last5=Shimizu |first5=Shinkichi|last6=Shoji|first6=Takayuki|last7=Watanabe|first7=Nanao |year=2007|doi=10.1002/14356007.a22_399|title=Pyridine and Pyridine Derivatives|isbn=978-3527306732}}

:H₃CC₅H₄N + NH₃ + 1.5 O₂ → NCC₅H₄N + 3 H₂O

Nicotinonitrile is a precursor to the vitamin niacin.{{cite book |last1=Eggersdorfer |first1=Manfred |last2=Adam |first2=Geo |last3=John |first3=Michael |last4=Hähnlein |first4=Wolfgang |last5=Labler |first5=Ludvik |last6=Baldenius |first6=Kai-U. |last7=von dem Bussche-Hünnefeld |first7=Linda |last8=Hilgemann |first8=Eckhard |last9=Hoppe |first9=Peter |last10=Stürmer |first10=Rainer |last11=Weber |first11=Fritz |last12=Rüttimann |first12=August |last13=Moine |first13=Gérard |last14=Hohmann |first14=Hans-Peter |last15=Kurth |first15=Roland |last16=Paust |first16=Joachim |last17=Hähnlein |first17=Wolfgang |last18=Pauling |first18=Horst |last19=Weimann |first19=Bernd-Jürgen |last20=Kaesler |first20=Bruno |last21=Oster |first21=Bernd |last22=Fechtel |first22=Ulrich |last23=Kaiser |first23=Klaus |last24=de Potzolli |first24=Bernd |last25=Casutt |first25=Michael |last26=Koppe |first26=Thomas |last27=Schwarz |first27=Michael |last28=Weimann |first28=Bernd-Jürgen |last29=Hengartner |first29=Urs |last30=de Saizieu |first30=Antoine |last31=Wehrli |first31=Christof |last32=Blum |first32=René |title=Vitamins |date=2000 |publisher=Wiley-VCH Verlag GmbH & Co. KGaA |isbn=978-3527306732 |pages=148–150 |language=en|doi=10.1002/14356007.a27_443 }}

Nitrilase-catalyzed hydrolysis of 3-cyanopyridine by means of immobilized Rhodococcus rhodochrous J1 strains leads in quantitative yield to nicotinamide (vitamin B₃).{{cite journal|title = Nitrile Hydratase-Catalyzed Production of Nicotinamide from 3-Cyanopyridine in Rhodococcus rhodochrous J1|first1 = Toru|last1 = Nagasawa|first2 = Caluwadewa Deepal|last2 = Mathew|first3 = Jacques|last3 = Mauger|first4 = Hideaki|last4 = Yamada|journal = Appl. Environ. Microbiol.|year = 1988|volume = 54|issue = 7|pages = 1766–1769|doi = 10.1128/AEM.54.7.1766-1769.1988|pmid = 16347686|pmc = 202743|bibcode = 1988ApEnM..54.1766N|doi-access = free}}{{cite book|title = White Biotechnology|editor1-first = Roland|editor1-last = Ulber|editor2-first = Dieter|editor2-last = Sell|chapter = Building Blocks|volume = 105|series = Advances in Biochemical Engineering / Biotechnology|isbn = 9783540456957|doi = 10.1007/10_033|pmid = 17408083|pages = 133–173|chapter-url = https://books.google.com/books?id=_tXoG93OWHgC&pg=PA141|publisher = Springer Science & Business Media|year = 2007|last1 = Hilterhaus|first1 = L.|last2 = Liese|first2 = A.}}{{cite book|title = Biocatalysis in Organic Synthesis 1|series = Science of Synthesis|publisher = Georg Thieme Verlag|year = 2015|chapter = Enzymatic Synthesis of Amides|first1 = J. W.|last1 = Schmidberger|first2 = L. J.|last2 = Hepworth|first3 = A. P.|last3 = Green|first4 = S. L.|last4 = Flitsch|pages = 329–372|isbn = 9783131766113|editor1-first = Kurt|editor1-last = Faber|editor2-first = Wolf-Dieter|editor2-last = Fessner|editor3-first = Nicholas J.|editor3-last = Turner|chapter-url = https://books.google.com/books?id=8h_wBgAAQBAJ&pg=PA362}} The enzyme allows for a more selective synthesis as further hydrolysis of the amide to nicotinic acid is avoided.{{cite journal|title = Biocatalysis|first1 = Michael|last1 = Petersen|first2 = Andreas|last2 = Kiener|doi = 10.1039/A809538H|journal = Green Chem.|year = 1999|volume = 1|issue = 2|pages = 99–106}}

Oxidation of 3-cyanopyridine with hydrogen peroxide gives 3-cyanopyridine N-oxide, which hydrolyzes to nicotinic acid N-oxide, a precursor to pharmaceuticals.