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3-Cyanopyridine

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Name

3-Cyanopyridine

EINECS 202-863-0
CAS No. 100-54-9 Density 1.159 g/cm3
PSA 36.68000 LogP 0.95328
Solubility 140 g/L (20 °C) in water Melting Point 48-52 °C(lit.)
Formula C6H4N2 Boiling Point 202.985 °C at 760 mmHg
Molecular Weight 104.111 Flash Point 84.444 °C
Transport Information N/A Appearance white to beige solid
Safety 22-24/25-36/37/39-26 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 100-54-9 (3-Cyanopyridine) Hazard Symbols HarmfulXn
Synonyms

Nicotinonitrile(8CI);3-Azabenzonitrile;3-Pyridinenitrile;3-Pyridylcyanide;3-Pyridylcarbonitrile;NSC 17558;Nicotinic acid nitrile;b-Cyanopyridine;3-Pyridinecarbonitrile;

Article Data 362

3-Cyanopyridine 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.

3-Cyanopyridine Chemical Properties

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℃).

3-Cyanopyridine 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.

3-Cyanopyridine 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.

3-Cyanopyridine Consensus Reports

Reported in EPA TSCA Inventory.

3-Cyanopyridine 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
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