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100-54-9

Basic Information
CAS No.: 100-54-9
Name: 3-Cyanopyridine
Article Data: 362
Molecular Structure:
Molecular Structure of 100-54-9 (3-Cyanopyridine)
Formula: C6H4N2
Molecular Weight: 104.111
Synonyms: Nicotinonitrile(8CI);3-Azabenzonitrile;3-Pyridinenitrile;3-Pyridylcyanide;3-Pyridylcarbonitrile;NSC 17558;Nicotinic acid nitrile;b-Cyanopyridine;3-Pyridinecarbonitrile;
EINECS: 202-863-0
Density: 1.159 g/cm3
Melting Point: 48-52 °C(lit.)
Boiling Point: 202.985 °C at 760 mmHg
Flash Point: 84.444 °C
Solubility: 140 g/L (20 °C) in water
Appearance: white to beige solid
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38
Safety: 22-24/25-36/37/39-26
PSA: 36.68000
LogP: 0.95328
Synthetic route
98-92-0

nicotinamide

100-54-9

pyridine-3-carbonitrile

Conditions
ConditionsYield
With N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; copper(l) chloride In toluene at 100℃; for 24h;99%
With 3 A molecular sieve at 150 - 500℃; under 0.001 Torr; for 0.666667h; Pyrolysis;98%
With oxalyl dichloride; triethylamine; Triphenylphosphine oxide In acetonitrile at 20℃; for 0.166667h;96%
500-22-1

3-pyridinecarboxaldehyde

100-54-9

pyridine-3-carbonitrile

Conditions
ConditionsYield
With ammonium sulfate; sodium carbonate; sulfur In dimethyl sulfoxide at 120℃; for 10h; Sealed tube;99%
With ammonia; oxygen In ethanol; water for 1.5h; Reflux;94%
With hydroxylamine hydrochloride; pyrographite; methanesulfonyl chloride at 100℃; for 1h;92%
100-55-0

3-hydroxymethylpyridin

100-54-9

pyridine-3-carbonitrile

Conditions
ConditionsYield
Stage #1: 3-hydroxymethylpyridin With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere;
99%
With ammonia; oxygen In tert-Amyl alcohol; water at 100℃; under 3750.38 Torr; for 4h; Autoclave; High pressure;99%
With potassium phosphate; ammonium formate In acetonitrile at 115℃; for 16h; Sealed tube; Green chemistry;91%
1120-90-7

3-iodopyridine

773837-37-9

sodium cyanide

100-54-9

pyridine-3-carbonitrile

Conditions
ConditionsYield
With C18H14CuIN4 In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation;99%
108-99-6

3-Methylpyridine

100-54-9

pyridine-3-carbonitrile

Conditions
ConditionsYield
With manganese; ammonia; oxygen; pyrographite at 335℃; Temperature;98.7%
With ammonia In water at 200 - 300℃; Concentration;97%
With aluminum oxide; ammonia; oxygen at 300℃; Concentration; Temperature;93.1%
626-55-1

3-Bromopyridine

potassium hexacyanoferrate(II) trihydrate

100-54-9

pyridine-3-carbonitrile

Conditions
ConditionsYield
With Palladium Nanoparticles with two shape-persistent covalent cages CC1' In N,N-dimethyl-formamide at 140℃; for 15h; Reagent/catalyst; Inert atmosphere;98%
4621-66-3

thionicotinamide

100-54-9

pyridine-3-carbonitrile

Conditions
ConditionsYield
With tellurium tetrachloride; triethylamine In chloroform for 3h; Ambient temperature;96%
With methylene blue; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; Sealed tube; Irradiation;95%
With bis(tri-n-butyltin)oxide In benzene for 0.5h; Heating;92%
1193-92-6

3-pyridinealdoxime

100-54-9

pyridine-3-carbonitrile

Conditions
ConditionsYield
With thionyl chloride; polyvinylpyrrolidone In dichloromethane at 20℃; for 0.25h; Dehydration;95%
With 1,4-diaza-bicyclo[2.2.2]octane; trichlorophosphate In dichloromethane at 20℃; for 0.0833333h;94%
With aluminium trichloride; sodium iodide In acetonitrile for 2.5h; Heating;92%
1120-90-7

3-iodopyridine

151-50-8

potassium cyanide

100-54-9

pyridine-3-carbonitrile

Conditions
ConditionsYield
With tributyltin chloride; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In acetonitrile at 22℃; for 3h;95%
626-60-8

3-Chloropyridine

potassium ferrocyanide

100-54-9

pyridine-3-carbonitrile

Conditions
ConditionsYield
With sodium carbonate; palladium diacetate In 1-methyl-pyrrolidin-2-one; Hexadecane at 160℃; for 16h;95%
With sodium carbonate; cyclopalladated ferrocenylimine tricyclohexylphosphine In 1-methyl-pyrrolidin-2-one at 140℃; for 18h;82%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 16h;57%
With tetra(adamantyl)biphosphine; palladium diacetate; sodium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 16h; Inert atmosphere;66 %Chromat.
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Chemistry

Nicotinonitrile(100-54-9) exists as white to off-white crystalline powder, insoluble in water, soluble in ethanol, benzene and other organic solvents.
Molecular Structure:
Molecular Formula: C6H4N2.
Molecular Weight: 104.11.
Density: 1.159.
Melting Point: 49 - 50 ℃.
Boiling Point: 202 ℃.
Flash Point: 85 ℃.
Solubility: 140 g/L (20℃).

Uses

Nicotinonitrile(100-54-9) is used as the intermediates of rodenticides in organic synthesis. Besides, Nicotinonitrile(100-54-9) is the intermediates of medicines, dyes, fodders, resins and so on.

Toxicity Data With Reference

1.   

orl-rat LD50:1185 mg/kg

   MEPAAX    Medycyna Pracy. Industrial Medicine. 30 (1979),109.
2.   

ipr-mus LD25:810 mg/kg

   JPMSAE    Journal of Pharmaceutical Sciences. 64 (1975),528.
3.   

skn-rbt LDLo:4000 mg/kg

   MEPAAX    Medycyna Pracy. Industrial Medicine. 30 (1979),109.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by ingestion, intraperitoneal, and skin contact routes. When heated to decomposition it emits toxic vapors of NOx.
Hazard Codes: Xn
Risk Statements: 22-36/37/38
22: Harmful if swallowed 
36/37/38: Irritating to eyes, respiratory system and skin 
Safety Statements: 22-24/25-36/37/39-26
22: Do not breathe dust 
24/25: Avoid contact with skin and eyes 
36/37/39: Wear suitable protective clothing, gloves and eye/face protection 
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
WGK Germany: 3
RTECS: QT3030000
HS Code: 29333999