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4-Cyanopyridine

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4-Cyanopyridine Basic information

Product Name:
4-Cyanopyridine
Synonyms:
  • ISONICOTINIC ACID NITRILE
  • ISONICOTINONITRILE
  • AKOS BBS-00004486
  • 4-PYRIDINECARBONITRILE
  • 4-CYANOPYRIDINE
  • 4-Pyridinecarbonitrile 98%
  • Topiroxostat impurity B(Isoniazid Impurity 5)
  • 4-cyanopyridine (4-CP)
CAS:
100-48-1
MF:
C6H4N2
MW:
104.11
EINECS:
202-856-2
Product Categories:
  • Heterocycle-Pyridine series
  • cyanide
  • Pyridines derivates
  • bc0001
Mol File:
100-48-1.mol
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4-Cyanopyridine Chemical Properties

Melting point:
76-79 °C(lit.)
Boiling point:
196 °C
Density 
1.1145 (rough estimate)
vapor pressure 
41.9Pa at 25℃
refractive index 
1.5242 (estimate)
Flash point:
88 °C
storage temp. 
Sealed in dry,Room Temperature
solubility 
40g/l
pka
pK1:1.90(+1) (25°C)
form 
Crystals or Powder
color 
White to off-white
Water Solubility 
3.2 g/100ml (16.4 ºC)
BRN 
107712
Exposure limits
NIOSH: IDLH 25 mg/m3
Stability:
Stable. Incompatible with strong bases, strong oxidizing agents, strong acids.
InChIKey
GPHQHTOMRSGBNZ-UHFFFAOYSA-N
LogP
0.46 at 25℃
CAS DataBase Reference
100-48-1(CAS DataBase Reference)
NIST Chemistry Reference
4-Pyridinecarbonitrile(100-48-1)
EPA Substance Registry System
4-Pyridinecarbonitrile (100-48-1)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
20/21/22
Safety Statements 
36/37-24/25
RIDADR 
3276
WGK Germany 
3
TSCA 
Yes
PackingGroup 
III
HS Code 
29333999

MSDS

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4-Cyanopyridine Usage And Synthesis

Chemical Properties

beige solid

Chemical Properties

The cyanopyridines are as follows: 2-cyano-: A white to tan liquid or solid. Almond odor. Boiling point=2213℃ ; freezing/melting point=27℃ ; flash point=89℃ . 3-cyano-: a colorless liquid or gray crystal- line solid.

Uses

4-Cyanopyridine is used as an intermediate in organic synthesis and pharmaceutical substances like isonicotinylhydrazide, which is used in the treatment of tuberculosis. It is used as a precursor for the preparation of isonicotinic acid and 4-diemthylaminopyridine (DMAP). It is involved in the synthesis of 6-methyl-2-pyridin-4-yl-pyrimidin-4-ylamine by reacting with acetonitrile.

Synthesis

4-Cyanopyridine is synthesised by the reaction of 4-methylpyridine with ammonia and air in the presence of a catalyst. The specific synthesis steps are as follows:
4-Methylpyridine and ammonia vaporisation preheating to 180-330°C, then into the mixing tank and air mixing uniformly, into the fixed-bed reactor by the top of the fixed-bed reactor after the distribution of the catalyst-filled reactor, the control of the reaction temperature in the range of 330-450 ° C, the reaction head pressure is controlled in the range of 0.020-0.070 KPa, the reaction temperature is controlled by molten salts, the reaction gas after the end of the reaction After the reaction, the reaction gas was condensed to sub-zero fractionation to obtain the crude product of 4-cyanopyridine, and the crude product was distilled to obtain the finished product of 4-cyanopyridine. The conversion rate of 4-methylpyridine was above 99%, and the yield of 4-cyanopyridine was above 98%.

Potential Exposure

Limits in Air NIOSH IDLH525 mg/m3 NIOSH REL: (nitriles) 2 ppm, Ceiling Concentration, not to be exceeded in any 15-minute work period.

Shipping

UN3276 Nitriles, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required, Potential Inhalation Hazard (Special Provision 5).

Incompatibilities

Oxidizing agents, such as perchlorates, peroxides, and permanganates. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give car- boxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids .

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