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Pyridine

Pyridine
Full structural formula of pyridine
Skeletal formula of pyridine, showing the numbering convention
Ball-and-stick diagram of pyridine
Space-filling model of pyridine
Pyridine sample.jpg
Names
Preferred IUPAC name
Pyridine
Other names
Azine
Azabenzene
Identifiers
110-86-1 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:16227 N
ChEMBL ChEMBL266158 YesY
ChemSpider 1020 YesY
ECHA InfoCard 100.003.464
EC Number 203-809-9
KEGG C00747 YesY
PubChem 1049
UNII NH9L3PP67S YesY
Properties
C5H5N
Molar mass 79.10 g·mol−1
Appearance colorless to yellow liquid
Odor nauseating, fish-like
Density 0.9819 g/mL
Melting point −41.6 °C (−42.9 °F; 231.6 K)
Boiling point 115.2 °C (239.4 °F; 388.3 K)
Miscible
Vapor pressure 16 mmHg (20 °C)
Acidity (pKa) 5.25 (for the conjugate acid)
1.5093
Viscosity 0.88 cP
2.2 D
Hazards
Safety data sheet See: data page
Flammable (F)
Harmful (Xn)
R-phrases R20 R21 R22 R34 R36 R38
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 21 °C (70 °F; 294 K)
Explosive limits 1.8%–12.4%
5 ppm (TWA)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
891 mg/kg (rat, oral)
1500 mg/kg (mouse, oral)
1580 mg/kg (rat, oral)
9000 ppm (rat, 1 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 5 ppm (15 mg/m3)
REL (Recommended)
TWA 5 ppm (15 mg/m3)
IDLH (Immediate danger)
1000 ppm
Related compounds
Related amines
Picoline
Quinoline
Related compounds
Aniline
Pyrimidine
Piperidine
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one methine group (=CH−) replaced by a nitrogen atom. The pyridine ring occurs in many important compounds, including azines and the vitamins niacin and pyridoxine.

Pyridine was discovered in 1849 by the Scottish chemist Thomas Anderson as one of the constituents of bone oil. Two years later, Anderson isolated pure pyridine through fractional distillation of the oil. It is a colorless, highly flammable, weakly alkaline, water-soluble liquid with a distinctive, unpleasant fish-like smell.

Pyridine is used as a precursor to agrochemicals and pharmaceuticals and is also an important solvent and reagent. Pyridine is added to ethanol to make it unsuitable for drinking (see denatured alcohol). It is used in the in vitro synthesis of DNA, in the synthesis of sulfapyridine (a drug against bacterial and viral infections), antihistaminic drugs tripelennamine and mepyramine, as well as water repellents, bactericides, and herbicides. Some chemical compounds, although not synthesized from pyridine, contain its ring structure. They include B vitamins niacin and pyridoxal, the anti-tuberculosis drug isoniazid, nicotine and other nitrogen-containing plant products. Historically, pyridine was produced from coal tar and as a byproduct of coal gasification. However, increased demand for pyridine resulted in the development of more economical methods of synthesis from acetaldehyde and ammonia, and more than 20,000 tonnes per year are manufactured worldwide.


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