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2-Amino-3-picoline

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  • What is 2-Amino-3-picoline?
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  • Apr 9,2024
2-Amino-3-picoline Basic information
Product Name:2-Amino-3-picoline
Synonyms:AURORA KA-876;2-AMINO-3-PICOLINE 96%;2-amino-3-methyl-pyridin;2-Amino-beta-picoline;2-Pyridinamine,3-methyl-;3-Methyl-2-aminopyridine;3-methyl-2-pyridinamin;3-Methyl-2-pyridinamine
CAS:1603-40-3
MF:C6H8N2
MW:108.14
EINECS:216-501-4
Product Categories:amine;Pyridine;Pyridines derivates;Pyridine series;Pyridines, Pyrimidines, Purines and Pteredines;VARIOUSAMINE;bc0001
Mol File:1603-40-3.mol
2-Amino-3-picoline Structure
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.)
Fp 233 °F
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility 1000g/l
pkapK1: 7.24(+1) (25°C)
form Liquid After Melting
color Clear yellow
Water Solubility SOLUBLE
Sensitive Hygroscopic
BRN 107892
InChI1S/C6H8N2/c1-5-3-2-4-8-6(5)7/h2-4H,1H3,(H2,7,8)
InChIKeyRGDQRXPEZUNWHX-UHFFFAOYSA-N
SMILESCc1cccnc1N
CAS DataBase Reference1603-40-3(CAS DataBase Reference)
NIST Chemistry Reference2-Pyridinamine, 3-methyl-(1603-40-3)
EPA Substance Registry System2-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 TSCA listed
HazardClass 6.1
PackingGroup II
HS Code 29333999
Storage Class6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials
Hazard ClassificationsAcute Tox. 2 Dermal
Acute Tox. 3 Inhalation
Acute Tox. 3 Oral
Aquatic Chronic 3
Eye Dam. 1
Skin Corr. 1B
MSDS Information
ProviderLanguage
2-Amino-3-picoline English
SigmaAldrich English
ACROS English
ALFA English
2-Amino-3-picoline Usage And Synthesis
Chemical Properties2-Amino-3-picoline is CLEAR YELLOW LIQUID AFTER MELTING
Uses2-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
HazardToxic by ingestion.
Synthesis
3-Picoline

108-99-6

2-Amino-5-methylpyridine

1603-41-4

2-Amino-3-picoline

1603-40-3

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 MethodsRecrystallise 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
Tag:2-Amino-3-picoline(1603-40-3) Related Product Information
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