1603-40-3

Basic information

• Product Name: 2-Amino-3-picoline
• Synonyms: AURORA KA-876;2-AMINO-3-PICOLINE 96%;2-AMINO-3-METHYL-PYRIDIN,99%;2-AMINO-3-METHYL PYRIDINE 3-METHYLPYRIDIN-2-YLAMINE;2-AMINO-3-METHYLPYRIDINE (2-AMINO-3-PICOLINE);2-Amino-3-methylpyridine ,99%;2-Amino-3-picoline,96%;2-Amino-3-methylpyridine ,98.5%
• CAS NO: 1603-40-3
• Molecular Formula: C₆H₈N₂
• Molecular Weight: 108.14
• EINECS: 216-501-4
• Product Categories: VARIOUSAMINE;Pyridines, Pyrimidines, Purines and Pteredines;Pyridine series;Pyridine;Pyridines derivates;amine
• Mol File: 1603-40-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: 29-31 °C(lit.)
• Boiling Point: 221-222 °C(lit.)
• Flash Point: 233 °F
• Appearance: Clear yellow/Liquid After Melting
• Density: 1.073 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.11mmHg at 25°C
• Refractive Index: n20/D 1.5823(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 1000g/l
• PKA: pK1: 7.24(+1) (25°C)
• Water Solubility: SOLUBLE
• Sensitive: Hygroscopic
• BRN: 107892
• CAS DataBase Reference: 2-Amino-3-picoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3-picoline(1603-40-3)
• EPA Substance Registry System: 2-Amino-3-picoline(1603-40-3)

Safety Data

• Hazard Codes: T
• 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
• Hazardous Substances Data: 1603-40-3(Hazardous Substances Data)

Usage

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.

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].

InChI:InChI=1/C6H8N2/c1-5-3-2-4-8-6(5)7/h2-4H,1H3,(H2,7,8)/p+1

Synthetic route

2-bromo-3-picoline (3430-17-9) → 3-methylpyridin-2-ylamine (1603-40-3)

Conditions	Yield
With copper(I) oxide; potassium carbonate; ammonium hydroxide; N,N-dimethylethylenediamine In ethylene glycol at 60℃; for 16h; Inert atmosphere;	98%

N-Cyclohexyl-8-methyl-2-phenylimidazo[1,2-a]pyridin-3-amine → 3-methylpyridin-2-ylamine (1603-40-3) + N-cicloesil-α-ossofenilacetamide (724-92-5)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 96%

3-methyl-2-pyridinecarboxamide (937648-82-3) → 3-methylpyridin-2-ylamine (1603-40-3)

Conditions	Yield
With sodium hypobromide; water; sodium hydroxide at 0 - 60℃; for 0.5h; Hofmann Rearrangement;	87.8%

N-cyclohexyl-2-isopropyl-8-methylimidazo[1,2-a]pyridin-3-amine (553626-46-3) → 3-methylpyridin-2-ylamine (1603-40-3) + N-cyclohexyl-3-methyl-2-oxobutanamide (32998-89-3)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 74%

N-cyclohexyl-2-ethyl-8-methylimidazo[1,2-a]pyridin-3-amine → 3-methylpyridin-2-ylamine (1603-40-3) + N-cyclohexyl-2-oxobutanamide (5070-30-4)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 72%

2-fluoro-3-methylpyridine (2369-18-8) → 3-methylpyridin-2-ylamine (1603-40-3)

Conditions	Yield
With acetamidine hydrochloride; sodium hydroxide In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; chemoselective reaction;	43%

3-Methylpyridine (108-99-6) → (5-methyl-pyridin-2-yl)amine (1603-41-4) + 3-methylpyridin-2-ylamine (1603-40-3)

Conditions	Yield
With sodium amide; xylene
With ammonia; sodium; ethanolamine In toluene at 60 - 170℃; under 22502.3 - 41254.1 Torr; Pressure; Temperature; Autoclave; Inert atmosphere; Large scale;	A 1928 g B 144 g

3-Methylpyridine (108-99-6) → 3-methylpyridin-2-ylamine (1603-40-3)

Conditions	Yield
With sodium amide; xylene at 135 - 140℃;
With sodium amide In o-xylene Chichibabin reaction;

tetrachloromethane (56-23-5) + 3-Methylpyridine (108-99-6) + sodium amide → 3-methylpyridin-2-ylamine (1603-40-3)

2,2-dimethyl-3-(3-methyl-pyridin-2-yl)-2,3-dihydro-benzo[e][1,3]oxazin-4-one → 3-methylpyridin-2-ylamine (1603-40-3)

Conditions	Yield
With hydrogenchloride Hydrolysis;

3-picoline-N-oxide (1003-73-2) → (5-methyl-pyridin-2-yl)amine (1603-41-4) + 3-methylpyridin-2-ylamine (1603-40-3)

Conditions	Yield
Stage #1: 3-picoline-N-oxide With p-toluenesulfonylanhydride; tert-butylamine In various solvent(s) for 0.25h; Stage #2: With trifluoroacetic acid In various solvent(s) at 70℃; Further stages. Title compound not separated from byproducts.;

3-picoline-N-oxide (1003-73-2) → 3-methylpyridin-2-ylamine (1603-40-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: CH2Cl2 / Heating 2: conc. HCl View Scheme

2 chloro-3-methylpyridine (18368-76-8) → 3-methylpyridin-2-ylamine (1603-40-3)

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 2-[di-(3S,5S,7S)-adamantan-1-ylphosphino]-N,N-dimethylaniline; ammonia; sodium t-butanolate In 1,4-dioxane at 110 - 120℃; Buchwald-Hartwig amination; Inert atmosphere;

2 chloro-3-methylpyridine (18368-76-8) → 3-methylpyridin-2-ylamine (1603-40-3) + 3,3’-dimethyl-2,2’-dipyridylamine (6654-69-9)

Conditions	Yield
With diphenyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; diphenyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H58NO4PPdS; C50H58NO4PPdS; ammonia; sodium t-butanolate In 1,4-dioxane at 50℃; for 24h; Inert atmosphere;

N,N,N-tri-nbutyl-N-(5-chloro-4-hydroxy-3-((3-methylpyridin-2-ylimino)methyl)benzyl)-ammonium chloride → 3-methylpyridin-2-ylamine (1603-40-3) + 3-(3-formyl-5-chloro-4-hydroxybenzyl)-tri-nbutylammonium chloride

Conditions	Yield
With hydrogenchloride In water for 4h;

N,N,N-tri-nbutyl-N-(5-chloro-4-hydroxy-3-((3-methylpyridin-2-ylimino)methyl)benzyl)-ammonium hexafluorophosphate → 3-methylpyridin-2-ylamine (1603-40-3) + 3-(3-formyl-5-chloro-4-hydroxybenzyl)-tri-nbutylammonium hexafluorophosphate

Conditions	Yield
With hydrogenchloride In water for 4h;

5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane (5123-13-7) + C10H14N2O → 3-methylpyridin-2-ylamine (1603-40-3) + 3-methyl-N-(1-phenylbutyl)pyridin-2-amine + 2-n-butylamino-3-methylpyridine

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; isopropyl alcohol at 140℃; for 24h; Inert atmosphere; Sealed tube;	A 22 %Spectr. B 58 %Spectr. C 14 %Spectr.

3-methylpyridin-2-ylamine (1603-40-3) → 5-bromo-3-methyl-pyridin-2-ylamine (3430-21-5)

Conditions	Yield
Stage #1: 3-methylpyridin-2-ylamine With bromine In dichloromethane at 0 - 20℃; for 4.66667h; Stage #2: With sodium hydroxide In dichloromethane; water pH=9;	100%
With 1-butyl-3-methylpyridinium tribromide at 20℃;	97%
With bromine; iodine; acetic acid at 0 - 10℃; Reagent/catalyst; Temperature;	95.2%

3-methylpyridin-2-ylamine (1603-40-3) → 3-methylpiperidin-2-imine hydrochloride

Conditions	Yield
With hydrogenchloride; hydrogen; platinum(IV) oxide In ethanol; water under 2068.65 Torr; for 6.5h;	100%

3-methylpyridin-2-ylamine (1603-40-3) + Isophthalaldehyde (626-19-7) → C20H18N4 (1445377-27-4)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 110℃; for 17h; Dean-Stark;	100%

3-methylpyridin-2-ylamine (1603-40-3) + 1-methoxy-4-(2-nitro-vinyl)-benzene (3179-10-0) → 2-(4-methoxyphenyl)-8-methyl-3-nitroimidazo[1,2-a]pyridine

Conditions	Yield
With pyridine; tert.-butylhydroperoxide; iodine In acetonitrile at 100℃; for 12h; Green chemistry;	100%
With sodium iodide dichloride In water; N,N-dimethyl-formamide at 80℃; for 1.5h;	76%
With sodium iodine dichloride In water; N,N-dimethyl-formamide at 80℃; for 1.5h;	76%
With copper(II) nitrate In acetonitrile at 85℃; for 1h; Inert atmosphere; regioselective reaction;	1 g

3-methylpyridin-2-ylamine (1603-40-3) + 4-hydroxy-6-methyl-2-pyron (675-10-5) + pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) → 2-amino-3-methylpyridinium 3-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide (1367748-01-3)

Conditions	Yield
In chloroform for 3h; Reflux;	99%

3-methylpyridin-2-ylamine (1603-40-3) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) → 2-amino-3-methylpyridinium 3-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-2,4-dioxochroman-3-ide (1367747-98-5)

Conditions	Yield
In chloroform for 3h; Reflux;	99%

3-methylpyridin-2-ylamine (1603-40-3) + pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + 2-Hydroxy-1,4-naphthoquinone (83-72-7) → 2-amino-3-methylpyridinium 2-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-1,3,4-trioxo-1,2,3,4-tetrahydronaphthalen-2-ide (1367748-05-7)

Conditions	Yield
In chloroform for 1h; Reflux;	99%

3-methylpyridin-2-ylamine (1603-40-3) + 1,1-bis(diethylphosphono)ethylene (37465-31-9) → C16H30N2O6P2

Conditions	Yield
In chloroform at 20℃; for 1h;	99%

3-methylpyridin-2-ylamine (1603-40-3) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 8-methylimidazo[1,2-a]pyridine (874-10-2)

Conditions	Yield
With hydrogen bromide In ethanol; water at 90℃; for 26h;	98%
With sodium carbonate In 1,4-dioxane; water for 22h; Cyclization; Tschitschibabin reaction; Heating;	20%

pyridine-2-carbaldehyde (1121-60-4) + 3-methylpyridin-2-ylamine (1603-40-3) → N,N'-bis-(3-methyl-pyridin-2-yl)-C-pyridin-2-yl-methanediamine

Conditions	Yield
With 4 A molecular sieve In benzene at 80℃; for 5h;	98%

6-methyl-2-pyridinecarboxaldehyde (1122-72-1) + 3-methylpyridin-2-ylamine (1603-40-3) → (3-Methyl-pyridin-2-yl)-[1-(6-methyl-pyridin-2-yl)-meth-(E)-ylidene]-amine

Conditions	Yield
With 4 A molecular sieve In benzene at 80℃; for 5h;	98%

3-methylpyridin-2-ylamine (1603-40-3) + pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + 1,3-dimethylbarbituric acid (769-42-6) → 2-amino-3-methylpyridinium 5-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-ide (1367748-03-5)

Conditions	Yield
In chloroform for 4h; Reflux;	98%

3-methylpyridin-2-ylamine (1603-40-3) + acetoacetic acid methyl ester (105-45-3) → 2,9-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one (30247-65-5)

Conditions	Yield
With bismuth(III) chloride at 100℃; for 3h; Green chemistry;	98%

3-methylpyridin-2-ylamine (1603-40-3) + Cyclopropylacetylene (6746-94-7) + phenylglyoxal hydrate (1074-12-0) → 3-((1-cyclopropylvinyl)oxy)-8-methyl-2-phenylimidazo[1,2-a]pyridine

Conditions	Yield
Stage #1: 3-methylpyridin-2-ylamine; phenylglyoxal hydrate In 1,2-dichloro-benzene at 20℃; Sealed tube; Stage #2: Cyclopropylacetylene With copper(l) iodide In 1,2-dichloro-benzene at 120℃; for 5h; Sealed tube; regioselective reaction;	98%

3-methylpyridin-2-ylamine (1603-40-3) + ethyl (ethoxymethylene)cyanoacetate (94-05-3) → ethyl 2-cyano-3-(3-methyl-2-pyridylamino)acrylate

Conditions	Yield
In toluene at 100℃; for 0.25h;	97.8%

3-methylpyridin-2-ylamine (1603-40-3) + ibuprofen (15687-27-1) → 2-(4-isobutylphenyl)-N-(3-methylpyridin-2-yl)propanamide

Conditions	Yield
Stage #1: ibuprofen With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: 3-methylpyridin-2-ylamine In dichloromethane for 72h; Heating;	97%

3-methylpyridin-2-ylamine (1603-40-3) + acetophenone (98-86-2) → 3-iodo-8-methyl-2-phenylimidazo[1,2-a]pyridine (660432-29-1)

Conditions	Yield
With iodine; oxygen In 1,2-dichloro-benzene at 100℃; for 20h;	97%

3-methylpyridin-2-ylamine (1603-40-3) + n-octyne (629-05-0) + phenylglyoxal hydrate (1074-12-0) → 8-methyl-3-(oct-1-en-2-yloxy)-2-phenylimidazo[1,2-a]pyridine

Conditions	Yield
Stage #1: 3-methylpyridin-2-ylamine; phenylglyoxal hydrate In 1,2-dichloro-benzene at 20℃; Sealed tube; Stage #2: n-octyne With copper(l) iodide In 1,2-dichloro-benzene at 120℃; for 5h; Sealed tube; regioselective reaction;	97%

3-methylpyridin-2-ylamine (1603-40-3) + diethyl malonate (105-53-3) → 2-hydroxy-9-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (17326-09-9)

Conditions	Yield
at 150℃; for 24h;	96.5%
at 200℃; for 2h;	76%
at 170℃; for 12h; Neat (no solvent);

3-methylpyridin-2-ylamine (1603-40-3) + ethyl bromoacetate (105-36-2) → 2-amino-3-methyl-1-(2-ethoxy-2-oxoethyl)-pyridin-1-ium bromide

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 8h; Inert atmosphere;	96%
In tetrahydrofuran at 0 - 20℃; for 8h; Inert atmosphere;	96%
In diethyl ether for 48h; Ambient temperature;	82%

3-methylpyridin-2-ylamine (1603-40-3) + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) + phthalonitrile (91-15-6) → Co(3-MeBPI)2 (79062-08-1)

Conditions	Yield
With sodium hydroxide In methanol; toluene 1,2-dicyanobenzene and 2-amino-3-methylpyridine heated in oil bath to 210°C for 3 h, mixt. cooled to ambient temp., toluene added, temp.increased to 90°C, NaOH in methanol added, Co(OAc)2 in methanol added and mixt. heated for 1 h; mixt. cooled to 40°C, product filtered, washed with methanol, diethyl ether and dried;	96%
With sodium hydroxide In methanol; toluene 1,2-dicyanobenzene and 2-amino-3-methylpyridine heated in oil bath to 210°C for 4 h, mixt. cooled to 210°C., toluene added, NaOH in methanol added and stirred for 5 min, Co(OAc)2 in methanol added and mixt. stirredd for 45 min; mixt. cooled to 40°C, product filtered, washed with methanol, diethyl ether and dried in vacuo at 80°C;

3-methylpyridin-2-ylamine (1603-40-3) + phenylacetaldehyde (122-78-1) → 8-methyl-3-phenyl-H-imidazo[1,2-a]pyridine

Conditions	Yield
With sulfur In cyclohexane; dimethyl sulfoxide at 120℃; for 1h; Sealed tube;	96%
Multi-step reaction with 2 steps 1: N-iodo-succinimide / dichloromethane / 1 h / 20 °C 2: sodium hydrogencarbonate / dichloromethane / 1.5 h View Scheme

3-methylpyridin-2-ylamine (1603-40-3) + para-bromophenacyl bromide (99-73-0) → 3-(4-bromophenyl)-8-methyl-H-imidazo[1,2-a]pyridine

Conditions	Yield
With fluconazole immobilized chloropropyl-modified Fe3O4-SiO2 core-shell nanoparticle In water at 60℃; for 2h;	96%

3-methylpyridin-2-ylamine (1603-40-3) + aconic acid (585-68-2) → 2-[9-methyl-2-oxo-2H-pyrido[1,2-a]pyrimidin-3(4H)-ylidene]acetic acid

Conditions	Yield
In ethanol at 20℃;	96%

3-methylpyridin-2-ylamine (1603-40-3) + phenylglyoxal hydrate (1074-12-0) + hex-1-yne (693-02-7) → 3-(hex-1-en-2-yloxy)-8-methyl-2-phenylimidazo[1,2-a]pyridine

Conditions	Yield
Stage #1: 3-methylpyridin-2-ylamine; phenylglyoxal hydrate In 1,2-dichloro-benzene at 20℃; Sealed tube; Stage #2: hex-1-yne With copper(l) iodide In 1,2-dichloro-benzene at 120℃; for 5h; Sealed tube; regioselective reaction;	96%

3-methylpyridin-2-ylamine (1603-40-3) + 2-Bromo-4'-phenylacetophenone (135-73-9) → 2-([1,1'-biphenyl]-4-yl)-8-methylimidazo[1,2-a]pyridine

Conditions	Yield
In water; isopropyl alcohol at 75℃; Microwave irradiation; Green chemistry;	95%

3-methylpyridin-2-ylamine (1603-40-3) + acetylene (74-86-2) → 1-Vinyl-3-methyl-2-pyridone (124695-16-5)

Conditions	Yield
cadmium(II) acetate In 1,4-dioxane; water at 160 - 165℃; for 3h; autoclave;	95%

Upstream product

• 110-86-1 pyridine 
• 1003-73-2 3-picoline-N-oxide 
• 407-25-0 trifluoroacetic anhydride 
• 937648-82-3 3-methyl-2-pyridinecarboxamide 
• 553626-46-3 N-cyclohexyl-2-isopropyl-8-methylimidazo[1,2-a]pyridin-3-amine 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 2369-18-8 2-fluoro-3-methylpyridine 
• 18368-76-8 2 chloro-3-methylpyridine 
• 3430-17-9 2-bromo-3-picoline 
• 56-23-5 tetrachloromethane 
• 108-99-6 3-Methylpyridine 

Downstream Products

• 18368-73-5 2-nitro-3-methylpyridine 
• 125537-85-1 N-(3-methyl-2-pyridyl)-N'-(p-tolyl)-thiourea 
• 893-16-3 8-methyl-2-(4-nitro-phenyl)-imidazo[1,2-a]pyridine 
• 298683-52-0 ethyl 1,1,1,3,3,3-hexafluoro-2-(3-methylpyridin-2-yl)aminoprop-2-yl carbamate 
• 59129-93-0 2-[(1E)-2-aza-2-(3-methyl(2-pyridyl))ethenyl]benzen-1-ol 
• 36952-41-7 4-methoxybenzylidene-(3-methyl-pyridin-2-yl)-imine 
• 225112-12-9 3-<(Benzyloxycarbonyl)amino>-9-methyl-4H-pyrido<1,2-a>pyrimidin-4-one 
• 69372-19-6 pemirolast 
• 220465-48-5 ethyl 8-methyl-2-phenylimidazo[1,2-a]pyridine-3-carboxylate 
• 136152-40-4 2-(triphenylphosphoranylidene)amino-3-picoline 
• 4931-46-8 N-(3-methyl-2-pyridinyl)formamide 
• 148926-70-9 (1)-2-dodecyl-N-(3-methyl-2-pyridinyl)-α-phenyl-2H-tetrazole-5-acetamide 
• 166266-19-9 2-amino-3-methyl-5-iodopyridine 

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