2-Amino-3-picoline Chemical Properties

Melting point:

29-31 °C (lit.)

Boiling point:

221-222 °C (lit.)

Density 

1.073 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.5823(lit.)

Flash point:

233 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

1000g/l

form 

Liquid After Melting

pka

pK1: 7.24(+1) (25°C)

color 

Clear yellow

Water Solubility 

SOLUBLE

Sensitive 

Hygroscopic

BRN 

107892

InChIKey

RGDQRXPEZUNWHX-UHFFFAOYSA-N

CAS DataBase Reference

1603-40-3(CAS DataBase Reference)

NIST Chemistry Reference

2-Pyridinamine, 3-methyl-(1603-40-3)

EPA Substance Registry System

2-Pyridinamine, 3-methyl- (1603-40-3)

Safety Information

Hazard Codes 

T

Risk Statements 

23/24/25-33-36/37/38-25

Safety Statements 

36/37/39-45-37/39-28A-26

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

US1850000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29333999

MSDS

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2-Amino-3-picoline Usage And Synthesis

Chemical Properties

2-Amino-3-picoline is CLEAR YELLOW LIQUID AFTER MELTING

Uses

2-Amino-3-picoline is used in the synthesis of ketones from aldehydes.

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 4453, 1973 DOI: 10.1021/ja00794a070

Hazard

Toxic by ingestion.

Synthesis

1) Add 9021 g of toluene, 538 g of sodium metal, 70 g of ethanolamine and 1900 g of 3-methylpyridine to the autoclave. After sealing the autoclave, open the feeding ports of the autoclave inlet and drip tank, and make sure the valves of the drip tank and the kettle are open. A hose was extended through the inlet port to the bottom of the kettle, and nitrogen was passed in to displace the air for 1 min, followed by closing the inlet cover. Heat the mixture to 60°C and slowly add liquid ammonia dropwise, maintaining the pressure in the autoclave at 3 MPa, until the total amount of liquid ammonia added reaches 600 g. 2) Increase the reaction temperature to 170°C and fill the autoclave with nitrogen until the pressure reaches 5 MPa to ensure that the reaction is fully carried out. When the pressure in the autoclave rose to 5.5 MPa, the pressure was released to 5 MPa and the process was repeated until the pressure no longer rose due to the reaction, indicating that the reaction was complete. The reaction system was then cooled to room temperature. 3) The ammoniated liquid was slowly added dropwise to 9 kg of water and the mixture was stirred to promote hydrolysis and extraction. After standing, the phases were separated and the aqueous phase was subjected to secondary extraction with 3 L of toluene. All organic phases were combined and the oil phase was quantitatively analyzed by gas chromatography to yield 1928 g of 2-amino-5-methylpyridine and 144 g of 2-amino-3-methylpyridine.

Purification Methods

Recrystallise the picoline three times from *benzene, most of the residual *benzene being removed from the crystals by standing over paraffin wax chips in an evacuated desiccator. The amine is also transferred to a separating funnel under N2, and left in contact with NaOH pellets for 3hours with occasional shaking. It is then placed in a vacuum distilling flask where it is refluxed gently in a stream of dry N2 before fractionally distilling it. [Mod et al. J Phys Chem 60 1651 1956, Beilstein 22/9 V 212].

References

[1] Patent: US2456379, 1946,
[2] Patent: CN106496105, 2017, A. Location in patent: Paragraph 0024; 0025; 0026; 0027; 0028; 0029; 0030-0035

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