Loading AI tools
Chemical compound From Wikipedia, the free encyclopedia
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:[2]
Names | |
---|---|
Preferred IUPAC name
Pyridine-3-carbonitrile | |
Identifiers | |
3D model (JSmol) |
|
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.002.603 |
EC Number |
|
PubChem CID |
|
UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
Properties | |
C6H4N2 | |
Molar mass | 104.112 g·mol−1 |
Density | 1.1590 |
Melting point | 51 °C (124 °F; 324 K) |
Boiling point | 206.9 °C (404.4 °F; 480.0 K) |
Vapor pressure | 0.296 mm Hg |
Structure[1] | |
Monoclinic | |
P21/c (No. 14) | |
a = 3.808 Å, b = 13.120 Å, c = 10.591 Å α = 90°, β = 97.97°, γ = 90° | |
Lattice volume (V) |
524 |
Formula units (Z) |
4 |
Hazards | |
GHS labelling: | |
Warning | |
H302, H315, H319, H335 | |
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 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Nicotinonitrile is a precursor to the vitamin niacin.[3]
Nitrilase-catalyzed hydrolysis of 3-cyanopyridine by means of immobilized Rhodococcus rhodochrous J1[2] strains leads in quantitative yield to nicotinamide (vitamin B3).[4][5][6] The enzyme allows for a more selective synthesis as further hydrolysis of the amide to nicotinic acid is avoided.[7]
Oxidation of 3-cyanopyridine with hydrogen peroxide gives 3-cyanopyridine N-oxide, which hydrolyzes to nicotinic acid N-oxide, a precursor to pharmaceuticals.
Seamless Wikipedia browsing. On steroids.
Every time you click a link to Wikipedia, Wiktionary or Wikiquote in your browser's search results, it will show the modern Wikiwand interface.
Wikiwand extension is a five stars, simple, with minimum permission required to keep your browsing private, safe and transparent.