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Basic Information
| CAS No.: | 100-54-9 |
|---|---|
| Name: | 3-Cyanopyridine |
| Article Data: | 362 |
| Molecular Structure: | |
|
|
|
| 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: |
 Xn
|
| Risk Codes: | 22-36/37/38 |
| Safety: | 22-24/25-36/37/39-26 |
| PSA: | 36.68000 |
| LogP: | 0.95328 |
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Synthetic route
Conditions
| Conditions | Yield |
|---|---|
| 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% |
Conditions
| Conditions | Yield |
|---|---|
| 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% |
Conditions
| Conditions | Yield |
|---|---|
| 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% |
Conditions
| Conditions | Yield |
|---|---|
| With C18H14CuIN4 In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation; | 99% |
Conditions
| Conditions | Yield |
|---|---|
| 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% |
Conditions
| Conditions | Yield |
|---|---|
| With Palladium Nanoparticles with two shape-persistent covalent cages CC1' In N,N-dimethyl-formamide at 140℃; for 15h; Reagent/catalyst; Inert atmosphere; | 98% |
Conditions
| Conditions | Yield |
|---|---|
| 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% |
Conditions
| Conditions | Yield |
|---|---|
| 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% |
Conditions
| Conditions | Yield |
|---|---|
| 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% |
Conditions
| Conditions | Yield |
|---|---|
| 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. |
Raw Materials
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3-Cyanopyridine
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℃).
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
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