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Nikotinonitril
Nama
	Nama IUPAC (preferensi) Piridina-3-karbonitril
Penanda
Nomor CAS	100-54-9;
Model 3D (JSmol)	Gambar interaktif;
ChEBI	CHEBI:86556;
ChEMBL	ChEMBL3181972;
ChemSpider	78;
Nomor EC
PubChem CID	79;
Nomor RTECS	{{{value}}}
UNII	X64V0K6260;
CompTox Dashboard (EPA)	DTXSID1026665 ;
	InChI InChI=1S/C6H4N2/c7-4-6-2-1-3-8-5-6/h1-3,5H Key: GZPHSAQLYPIAIN-UHFFFAOYSA-N;
	SMILES C1=CC(=CN=C1)C#N;
Sifat
Rumus kimia	C6H4N2
Massa molar	104,11 g·mol−1
Densitas	1.1590
Titik lebur	51 °C (124 °F; 324 K)
Titik didih	2.069 °C (3.756 °F; 2.342 K)
Tekanan uap	0.296 mm Hg
Struktur
Struktur kristal	Monoklinik
Grup ruang	P21/c (No. 14)
Konstanta kisi	a = 3.808 Å, b = 13.120 Å, c = 10.591 Å α = 90°, β = 97.97°, γ = 90°
Volum kisi (V)	524
Satuan formula (Z)	4
Bahaya
Piktogram GHS
Keterangan bahaya GHS	{{{value}}}
Pernyataan bahaya GHS	H302, H315, H319, H335
Langkah perlindungan GHS	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Kecuali dinyatakan lain, data di atas berlaku pada suhu dan tekanan standar (25 °C [77 °F], 100 kPa).
	Referensi

Nikotinonitril atau 3-sianopiridina adalah senyawa organik dengan rumus NCC₅H₄N. Molekulnya terdiri dari cincin piridina dengan gugus nitril yang terikat pada posisi 3. Senyawa ini merupakan padatan tak berwarna yang diproduksi melalui amoksidasi 3-metilpiridina:^[2]

H₃CC₅H₄N + NH₃ + 1.5 O₂ → NCC₅H₄N + 3 H₂O

Nikotinonitril merupakan prekursor vitamin niasin.^[3]

Hidrolisis 3-sianopiridina yang dikatalisis nitrilase dengan menggunakan galur Rhodococcus rhodochrous J1^[2] yang diimobilisasi menghasilkan nikotinamida (vitamin B₃) dalam jumlah kuantitatif.^[4]^[5]^[6] Enzim ini memungkinkan sintesis yang lebih selektif karena hidrolisis amida lebih lanjut menjadi asam nikotinat dapat dihindari.^[7]

Oksidasi 3-sianopiridina dengan hidrogen peroksida menghasilkan 3-sianopiridina N-oksida, yang terhidrolisis menjadi asam nikotinat N-oksida, suatu prekursor obat-obatan.

Referensi

^ Kubiak, R.; Janczak, J.; Śledź, M. (June 2002). "Crystal structures of 2- and 3-cyanopyridine". Journal of Molecular Structure. 610 (1–3): 59–64. Bibcode:2002JMoSt.610...59K. doi:10.1016/S0022-2860(02)00012-1.
^ ^a ^b Abe, Nobuyuki; Ichimura, Hisao; Kataoka, Toshiaki; Morishita, Sinji; Shimizu, Shinkichi; Shoji, Takayuki; Watanabe, Nanao (2005), "Pyridine and Pyridine Derivatives", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a22_399
^ Eggersdorfer, Manfred; Adam, Geo; John, Michael; Hähnlein, Wolfgang; Labler, Ludvik; Baldenius, Kai-U.; von dem Bussche-Hünnefeld, Linda; Hilgemann, Eckhard; Hoppe, Peter; Stürmer, Rainer; Weber, Fritz; Rüttimann, August; Moine, Gérard; Hohmann, Hans-Peter; Kurth, Roland; Paust, Joachim; Hähnlein, Wolfgang; Pauling, Horst; Weimann, Bernd-Jürgen; Kaesler, Bruno; Oster, Bernd; Fechtel, Ulrich; Kaiser, Klaus; de Potzolli, Bernd; Casutt, Michael; Koppe, Thomas; Schwarz, Michael; Weimann, Bernd-Jürgen; Hengartner, Urs; de Saizieu, Antoine; Wehrli, Christof; Blum, René (2000). Vitamins (dalam bahasa Inggris). Wiley-VCH Verlag GmbH & Co. KGaA. hlm. 148–150. doi:10.1002/14356007.a27_443. ISBN 978-3527306732.
^ Nagasawa, Toru; Mathew, Caluwadewa Deepal; Mauger, Jacques; Yamada, Hideaki (1988). "Nitrile Hydratase-Catalyzed Production of Nicotinamide from 3-Cyanopyridine in Rhodococcus rhodochrous J1". Appl. Environ. Microbiol. 54 (7): 1766–1769. Bibcode:1988ApEnM..54.1766N. doi:10.1128/AEM.54.7.1766-1769.1988. PMC 202743. PMID 16347686.
^ Hilterhaus, L.; Liese, A. (2007). "Building Blocks". Dalam Ulber, Roland; Sell, Dieter (ed.). White Biotechnology. Advances in Biochemical Engineering / Biotechnology. Vol. 105. Springer Science & Business Media. hlm. 133–173. doi:10.1007/10_033. ISBN 9783540456957. PMID 17408083.
^ Schmidberger, J. W.; Hepworth, L. J.; Green, A. P.; Flitsch, S. L. (2015). "Enzymatic Synthesis of Amides". Dalam Faber, Kurt; Fessner, Wolf-Dieter; Turner, Nicholas J. (ed.). Biocatalysis in Organic Synthesis 1. Science of Synthesis. Georg Thieme Verlag. hlm. 329–372. ISBN 9783131766113.
^ Petersen, Michael; Kiener, Andreas (1999). "Biocatalysis". Green Chem. 1 (2): 99–106. doi:10.1039/A809538H.

[1] Kubiak, R.; Janczak, J.; Śledź, M. (June 2002). "Crystal structures of 2- and 3-cyanopyridine". Journal of Molecular Structure. 610 (1–3): 59–64. Bibcode:2002JMoSt.610...59K. doi:10.1016/S0022-2860(02)00012-1.

[Ullmann-2] Abe, Nobuyuki; Ichimura, Hisao; Kataoka, Toshiaki; Morishita, Sinji; Shimizu, Shinkichi; Shoji, Takayuki; Watanabe, Nanao (2005), "Pyridine and Pyridine Derivatives", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a22_399

[3] Eggersdorfer, Manfred; Adam, Geo; John, Michael; Hähnlein, Wolfgang; Labler, Ludvik; Baldenius, Kai-U.; von dem Bussche-Hünnefeld, Linda; Hilgemann, Eckhard; Hoppe, Peter; Stürmer, Rainer; Weber, Fritz; Rüttimann, August; Moine, Gérard; Hohmann, Hans-Peter; Kurth, Roland; Paust, Joachim; Hähnlein, Wolfgang; Pauling, Horst; Weimann, Bernd-Jürgen; Kaesler, Bruno; Oster, Bernd; Fechtel, Ulrich; Kaiser, Klaus; de Potzolli, Bernd; Casutt, Michael; Koppe, Thomas; Schwarz, Michael; Weimann, Bernd-Jürgen; Hengartner, Urs; de Saizieu, Antoine; Wehrli, Christof; Blum, René (2000). Vitamins (dalam bahasa Inggris). Wiley-VCH Verlag GmbH & Co. KGaA. hlm. 148–150. doi:10.1002/14356007.a27_443. ISBN 978-3527306732.

[4] Nagasawa, Toru; Mathew, Caluwadewa Deepal; Mauger, Jacques; Yamada, Hideaki (1988). "Nitrile Hydratase-Catalyzed Production of Nicotinamide from 3-Cyanopyridine in Rhodococcus rhodochrous J1". Appl. Environ. Microbiol. 54 (7): 1766–1769. Bibcode:1988ApEnM..54.1766N. doi:10.1128/AEM.54.7.1766-1769.1988. PMC 202743. PMID 16347686.

[5] Hilterhaus, L.; Liese, A. (2007). "Building Blocks". Dalam Ulber, Roland; Sell, Dieter (ed.). White Biotechnology. Advances in Biochemical Engineering / Biotechnology. Vol. 105. Springer Science & Business Media. hlm. 133–173. doi:10.1007/10_033. ISBN 9783540456957. PMID 17408083.

[6] Schmidberger, J. W.; Hepworth, L. J.; Green, A. P.; Flitsch, S. L. (2015). "Enzymatic Synthesis of Amides". Dalam Faber, Kurt; Fessner, Wolf-Dieter; Turner, Nicholas J. (ed.). Biocatalysis in Organic Synthesis 1. Science of Synthesis. Georg Thieme Verlag. hlm. 329–372. ISBN 9783131766113.

[7] Petersen, Michael; Kiener, Andreas (1999). "Biocatalysis". Green Chem. 1 (2): 99–106. doi:10.1039/A809538H.

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Nikotinonitril

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