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3-Aminopyridine

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Name

3-Aminopyridine

EINECS 207-322-2
CAS No. 462-08-8 Density 1.107 g/cm3
PSA 38.91000 LogP 1.24500
Solubility It is soluble in water as well as soluble in alcohol, benzene. Melting Point 60-63 ºC(lit.)
Formula C5H6N2 Boiling Point 251 ºC at 760 mmHg
Molecular Weight 94.116 Flash Point 126 ºC
Transport Information UN 2671 6.1/PG 2 Appearance white to light yellow crystal powder
Safety 36/37/39-45-28-26 Risk Codes 23/24/25-33-36/37/38
Molecular Structure Molecular Structure of 462-08-8 (3-Aminopyridine) Hazard Symbols IrritantXi,ToxicT
Synonyms

pyridin-3-amine;Amino-3 pyridine;3-Pyridinamine;;3-Amino Pyridine;3-Pyridylamine;Pyridine, 3-amino-;beta-Aminopyridine;

Article Data 198

3-Aminopyridine Synthetic route

2530-26-9

3-nitropyridine

462-08-8

pyridin-3-ylamine

Conditions
ConditionsYield
With hydrogen In ethyl acetate at 20℃; under 7600.51 Torr; for 6h; Autoclave;99%
With 0.2C27H36N2*Pt; hydrogen In tetrahydrofuran at 60℃; under 3000.3 Torr; for 5h; chemoselective reaction;99%
With hydrogen In ethyl acetate under 760.051 Torr; for 2h; Heating; Flow reactor; Green chemistry;99%
4548-45-2

2-chloro-5-nitropyridine

462-08-8

pyridin-3-ylamine

Conditions
ConditionsYield
With cyclohexa-1,4-diene; 5%-palladium/activated carbon In methanol at 120℃; for 0.0833333h; Microwave irradiation;99%
With palladium 10% on activated carbon; hydrazine hydrate In methanol at 120℃; for 0.25h; Microwave irradiation;89%
With ethanol; palladium Hydrogenation;
5470-18-8

2-Chloro-3-nitropyridine

462-08-8

pyridin-3-ylamine

Conditions
ConditionsYield
With cyclohexa-1,4-diene; 5%-palladium/activated carbon In methanol at 120℃; for 0.0833333h; Microwave irradiation;99%
With hydrazine hydrate In ethanol at 70℃; for 4h; chemoselective reaction;95%
With palladium 10% on activated carbon; hydrazine hydrate In methanol at 120℃; for 0.25h; Microwave irradiation;84%
With palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate In methanol at 20℃; under 760.051 Torr; for 2h; Sealed tube; chemoselective reaction;100 %Spectr.
98-92-0

nicotinamide

462-08-8

pyridin-3-ylamine

Conditions
ConditionsYield
With sodium hypochlorite In water at 0 - 5℃;94.1%
With sodium hypochlorite at 5 - 10℃; Temperature;92.3%
With sodium hydroxide; bromine r.t., 30 min.; then 65-75 deg C, 2 h;62%
1657-32-5

3-aminopyridine-N-oxide

462-08-8

pyridin-3-ylamine

Conditions
ConditionsYield
With titanium tetrachloride; tin(ll) chloride In diethyl ether for 0.5h; Ambient temperature;94%
626-60-8

3-Chloropyridine

462-08-8

pyridin-3-ylamine

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 6h;94%
With ammonium hydroxide; potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation;94%
With C46H71Cl3N2Pd; ammonia; sodium t-butanolate In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; Schlenk technique;88%
1120-90-7

3-iodopyridine

462-08-8

pyridin-3-ylamine

Conditions
ConditionsYield
With iron(III) oxide; sodium hydroxide; copper(l) iodide; ammonia In ethanol; water at 90℃; for 16h;94%
With [N,N'-bis(5-sulfonatosalicylidene)-1,2-diaminoethane]copper disodium salt; ammonia; sodium hydroxide In water at 120℃; for 12h; sealed tube;94%
With copper(I) oxide; ammonium hydroxide; C17H14N2O3; potassium hydroxide In ethanol at 60℃; for 24h; Schlenk technique; Inert atmosphere;93%
100-54-9

pyridine-3-carbonitrile

462-08-8

pyridin-3-ylamine

Conditions
ConditionsYield
With sodium hypochlorite; sodium hydroxide In water at 5 - 20℃; Temperature;93.8%
Multi-step reaction with 2 steps
1: manganese(IV) oxide / ethanol; water / 6 h / 85 °C
2: sodium hydroxide; sodium hypochlorite / 6 h / 90 °C
View Scheme
626-55-1

3-Bromopyridine

462-08-8

pyridin-3-ylamine

Conditions
ConditionsYield
With [N,N'-bis(5-sulfonatosalicylidene)-1,2-diaminoethane]copper disodium salt; ammonia; sodium hydroxide In water at 120℃; for 12h; sealed tube;93%
Stage #1: 3-Bromopyridine With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide Inert atmosphere;
Stage #2: With ammonium hydroxide In dimethyl sulfoxide at 90℃; for 12h; Inert atmosphere;
93%
With oxalic acid hydrazide; ammonium hydroxide; tetrabutylammomium bromide; potassium carbonate; 2,5-hexanedione; copper(II) oxide In water at 90℃; for 1.33333h;90%
5867-45-8

N-(pyridin-3-yl)acetamide

462-08-8

pyridin-3-ylamine

Conditions
ConditionsYield
Stage #1: N-(pyridin-3-yl)acetamide With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.05h; Inert atmosphere;
Stage #2: With water In tetrahydrofuran Inert atmosphere;
89%

3-Aminopyridine Consensus Reports

Reported in EPA TSCA Inventory.

3-Aminopyridine Standards and Recommendations

DOT Classification:  6.1; Label: Poison

3-Aminopyridine Specification

The 3-Aminopyridine, with the CAS registry number 462-08-8, is also known as 3-Pyridinamine. It belongs to the product categories of Fine Chemical & Intermediates; Pyridine; Organics; Pyridine Series; Pyridines Derivates. Its EINECS registry number is 207-322-2. This chemical's molecular formula is C5H6N2 and molecular weight is 94.11. What's more, both its IUPAC name and systematic name are the same which is called Pyridin-3-amine. 3-Aminopyridine is an aminopyridine. This chemical can be prepared by nicotinamide.

Physical properties about 3-Aminopyridine are: (1)# of Rule of 5 Violations: 0; (2)#H bond acceptors: 2; (3)#H bond donors: 2; (4)#Freely Rotating Bonds: 1; (5)Polar Surface Area: 38.91 Å2; (6)Index of Refraction: 1.587; (7)Molar Refractivity: 28.58 cm3; (8)Molar Volume: 84.9 cm3; (9)Surface Tension: 51.2 dyne/cm; (10)Density: 1.107 g/cm3; (11)Flash Point: 126 °C; (12)Enthalpy of Vaporization: 48.83 kJ/mol; (13)Boiling Point: 251 °C at 760 mmHg; (14)Vapour Pressure: 0.021 mmHg at 25 °C.

Uses of 3-Aminopyridine: (1) it is used for intermediates of medicine and dye and it also can be used as analytical reagent; (2) it is used to produce other chemicals. For example, it can react with Formaldehyde to get Dimethyl-pyridin-3-yl-amine. The reaction occurs with reagents H2SO4 and zinc-powder.

3-Aminopyridine can react with Formaldehyde to get Dimethyl-pyridin-3-yl-amine.

When you are dealing with this chemical, you should be very careful. This chemical is toxic by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. Therefore, you could take off immediately all contaminated clothing. And you must wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: Nc1cccnc1
(2) InChI: InChI=1S/C5H6N2/c6-5-2-1-3-7-4-5/h1-4H,6H2
(3) InChIKey: CUYKNJBYIJFRCU-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 13300ug/kg (13.3mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
mouse LD50 intracrebral 4mg/kg (4mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Australian Journal of Experimental Biology and Medical Science. Vol. 36, Pg. 365, 1958.
mouse LD50 intraperitoneal 28mg/kg (28mg/kg)   Journal of Medicinal Chemistry. Vol. 8, Pg. 296, 1965.
mouse LD50 intravenous 24mg/kg (24mg/kg)   Annales Pharmaceutiques Francaises. Vol. 26, Pg. 345, 1968.
mouse LD50 subcutaneous 30mg/kg (30mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 226, Pg. 163, 1955.
quail LD50 oral 178mg/kg (178mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
 

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