2-Amino-5-methoxypyridine supplier

Name
5-METHOXY-PYRIDIN-2-YLAMINE
EINECS 125-856-9
CAS No. 10167-97-2
Article Data35
CAS DataBase
Density 1.139 g/cm³
Solubility
Melting Point 36-38 °C
Formula C₆H₈N₂O
Boiling Point 251.6 °C at 760 mmHg
Molecular Weight 124.142
Flash Point 106 °C
Transport Information
Appearance dark red oil
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Pyridine,2-amino-5-methoxy- (7CI,8CI);5-Methoxy-2-aminopyridine;5-Methoxypyridin-2-amine;
PSA 48.14000
LogP 1.25360

Synthetic route

: 638352-78-0
1-(5-methoxypyridin-2-yl)-2,5-dimethyl-1H-pyrrole

: 10167-97-2
2-amino-5-methoxypyridine

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; triethylamine In ethanol; water for 20h; Heating / reflux;	100%
With hydroxylamine hydrochloride; triethylamine In ethanol; water for 20h; Reflux;	100%
With hydroxylamine hydrochloride; triethylamine In ethanol; water for 20h; Heating;	81%

: 76066-07-4
2-bromo-3-methoxy-6-nitropyridine

: 10167-97-2
2-amino-5-methoxypyridine

Conditions

Conditions	Yield
With hydrazine; palladium 10% on activated carbon In ethanol for 0.75h; Heating / reflux;	96%
With hydrazine; palladium 10% on activated carbon In ethanol; water for 0.75h; Heating / reflux;	96%
With hydrazine hydrate; palladium on activated charcoal In ethanol for 1.5h; Heating;	95%

: 105170-27-2
2-bromo-5-methoxypyridine

: 10167-97-2
2-amino-5-methoxypyridine

Conditions

Conditions	Yield
With bis(triphenylphosphine)nickel(II) chloride; lithium hexamethyldisilazane In 1,4-dioxane at 90℃; for 2h; Glovebox; Sealed tube;	69%
With copper acetylacetonate; potassium phosphate; ammonia In N,N-dimethyl-formamide at 90℃; for 24h; Glovebox; Autoclave; chemoselective reaction;	66%

: 20511-12-0
2-amino-5-iodopyridine

: 67-56-1
methanol

: 10167-97-2
2-amino-5-methoxypyridine

Conditions

Conditions	Yield
With sodium; copper at 160℃; for 48h;	51%
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate at 110℃; Ullmann reaction;

: 1072-97-5
5-bromo-2-pyridylamine

: 124-41-4
sodium methylate

: 10167-97-2
2-amino-5-methoxypyridine

Conditions

Conditions	Yield
With copper In methanol at 100℃; for 12h;	44%
With copper In methanol at 135℃; for 14h;	36%
copper In methanol at 135℃; for 14h; Product distribution / selectivity;	36%

: 42900-89-0
3,4-dihydro-1H-2-benzopyran-3-ol

: 5-methoxy-2-(2-methylhydrazinyl)pyridinium bishydrochloride

A: 2-(5-methoxy-1H-indol-3-yl)phenylmethanol

B: 3-(2-(isopropoxymethyl)phenyl)-5-methoxy-1H-pyrrolo[2,3-b]pyridine

C: 3-(2-(chloromethyl)phenyl)-5-methoxy-1H-pyrrolo[2,3-b]pyridine

D: 10167-97-2
2-amino-5-methoxypyridine

Conditions

Conditions	Yield
In isopropyl alcohol at 80℃; for 24h; Fischer Indole Synthesis; Inert atmosphere;	A 34% B 4% C 4% D 13%

...Expand

: 20511-12-0
2-amino-5-iodopyridine

: 124-41-4
sodium methylate

: 10167-97-2
2-amino-5-methoxypyridine

Conditions

Conditions	Yield
With copper In methanol at 160℃;	31%

: 477889-91-1
1-(5-iodopyridin-2-yl)-2,5-dimethyl-1H-pyrrole

: 10167-97-2
2-amino-5-methoxypyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / copper(I) chloride / methanol; dimethylformamide / 2 h / 80 °C 2: 81 percent / hydroxylamine hydrochloride; triethylamine / ethanol; H2O / 20 h / Heating View Scheme

: 24100-18-3
2-bromo-3-methoxypyridine

: 10167-97-2
2-amino-5-methoxypyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / conc. H2SO4; fum. HNO3 / 4 h / 50 °C 2: 95 percent / N2H4*H2O / 5 percent Pd/C / ethanol / 1.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 48 percent / nitric acid, conc. sulfuric acid / 0.5 h / Heating 2: 78 percent / hydrazine hydrate / Pd/C / ethanol / 0.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 71 percent / fuming HNO3, concd H2SO4 / 1 h / 55 °C 2: 59 percent / H2, NaOH / 10percent Pd/C / ethanol View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / 3 h / 55 °C 2: palladium on activated charcoal; hydrogen; potassium acetate / methanol; ethyl acetate / 48 h / 50 °C / 2585.81 Torr View Scheme

: 20511-12-0
2-amino-5-iodopyridine

: 12775-96-1, 15158-11-9, 15721-63-8, 16941-75-6, 17493-86-6, 19498-52-3, 20499-83-6, 20499-84-7, 20499-85-8, 20499-86-9, 20573-10-8, 20573-11-9, 21595-51-7, 21595-52-8, 22206-52-6, 26445-28-3, 28959-95-7, 37362-93-9, 39417-05-5, 54603-16-6, 54603-23-5, 54603-32-6, 54603-40-6, 54603-48-4, 54603-81-5, 54603-89-3, 56316-56-4, 95985-91-4, 122297-32-9, 7440-50-8
copper

: 10167-97-2
2-amino-5-methoxypyridine

Conditions

Conditions	Yield
With sodium methylate In methanol

conc. aqueous ammonia: conc. aqueous ammonia

: 76066-07-4
2-bromo-3-methoxy-6-nitropyridine

: 10167-97-2
2-amino-5-methoxypyridine

Conditions

Conditions	Yield
With hydrazine hydrate; palladium-carbon In ethanol; water
With hydrazine hydrate; palladium-carbon In ethanol; water

: 6602-32-0
2-bromo-pyridin-3-ol

: 10167-97-2
2-amino-5-methoxypyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: diazomethyl-trimethyl-silane / dichloromethane; hexane / 3 h / 13 °C 2: sulfuric acid; nitric acid / 3 h / 55 °C 3: palladium on activated charcoal; hydrogen; potassium acetate / methanol; ethyl acetate / 48 h / 50 °C / 2585.81 Torr View Scheme

: 228710-82-5
5-bromo-2-(2,5-dimethyl-pyrrol-1-yl)-pyridine

: 10167-97-2
2-amino-5-methoxypyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide / N,N-dimethyl-formamide; methanol / 3 h / 80 °C 2: hydroxylamine hydrochloride; triethylamine / ethanol; water / 20 h / Reflux View Scheme

: 10167-97-2
2-amino-5-methoxypyridine

: 16182-04-0
Ethoxycarbonyl isothiocyanate

: 1092394-14-3
ethyl {[(5-methoxypyridin-2-yl)amino]carbonothioyl}carbamate

Conditions

Conditions	Yield
at 20℃;	100%
at 20℃;	100%

: 10167-97-2
2-amino-5-methoxypyridine

: 16182-04-0
Ethoxycarbonyl isothiocyanate

: 5-methoxypyridin-2-amine ethoxycarbonyl thiourea

Conditions

Conditions	Yield
In 1,4-dioxane at 20℃;	100%

: C21H26O3

: 10167-97-2
2-amino-5-methoxypyridine

: N-(5-methoxypyridin-2-yl)-3-((13S,15R)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl)propanamide

Conditions

Conditions	Yield
With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran for 2h; Reflux;	99%

: 2-(pyridin-3-yl)-1,3-benzoxazole-5-carbaldehyde

: 10167-97-2
2-amino-5-methoxypyridine

: 5-methoxy-N-{[2-(pyridin-3-yl)-1,3-benzoxazol-5-yl]methyl}pyridin-2-amine

Conditions

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; thiourea In toluene at 70℃; Molecular sieve; Inert atmosphere;	97%

: 23386-72-3
2-bromo-1-(1-hydroxycyclohexyl)ethanone

: 10167-97-2
2-amino-5-methoxypyridine

: 1-(6-methoxyimidazo[1,2-a]pyridin-2-yl)cyclohexanol

Conditions

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane at 110℃; for 12h; Sealed tube; Inert atmosphere;	91%

: 147410-78-4
3-(N-(4-chlorophenyl)sulfamoyl)benzoic acid

: 10167-97-2
2-amino-5-methoxypyridine

: 1586822-35-6
3-(N-(4-chlorophenyl)sulfamoyl)-N-(5-methoxypyridin-2-yl)benzamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	89%

: 10167-97-2
2-amino-5-methoxypyridine

: 82-86-0
acenaphthene quinone

: 2-(5-methoxypyridin-2-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions

Conditions	Yield
With oxygen; copper dichloride; Trimethylacetic acid In m-xylene; tert-butyl alcohol at 80 - 85℃; for 48h;	86%

: 62266-36-8
(+/-)-methylenecyclopropanecarboxylic acid

: 10167-97-2
2-amino-5-methoxypyridine

: 2-methylene-cyclopropanecarboxylic acid (5-methoxy-pyridin-2-yl)-amide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 30h;	85%

: 127-19-5
N,N-dimethyl acetamide

: 10167-97-2
2-amino-5-methoxypyridine

: 76066-09-6
N-(5-methoxy-2-pyridyl)acetamide

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl acetamide With 1,1'-carbonyldiimidazole at 120 - 125℃; for 0.5h; Inert atmosphere; Stage #2: 2-amino-5-methoxypyridine at 60 - 65℃; for 1.5h; Inert atmosphere;	84%

: 10167-97-2
2-amino-5-methoxypyridine

: 97-51-8
5-Nitrosalicylaldehyde

: (E)-2-(((5-methoxypyridin-2-yl)imino)methyl)-4-nitrophenol

Conditions

Conditions	Yield
In ethanol for 6h; Reflux;	83%

: 361473-14-5
3-(N-(4-chlorophenyl)-N-methylsulfamoyl)benzoic acid

: 10167-97-2
2-amino-5-methoxypyridine

: 1586822-59-4
3-(N-(4-chlorophenyl)-N-methylsulfamoyl)-N-(5-methoxypyridin-2-yl)benzamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	82%

: 90-02-8
salicylaldehyde

: 10167-97-2
2-amino-5-methoxypyridine

: (E)-2-(((5-methoxypyridin-2-yl)imino)methyl)phenol

Conditions

Conditions	Yield
In ethanol for 6h; Reflux;	82%

: 14003-96-4
8-formyl-4-methyl-7-hydroxycoumarin

: 10167-97-2
2-amino-5-methoxypyridine

: (E)-7-hydroxy-8-(((5-methoxypyridin-2-yl)imino)methyl)-4-methyl-2H-chromen-2-one

Conditions

Conditions	Yield
In methanol at 60℃; for 4h;	81%

: 3-((13S,15R)-4-fluoro-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl)propanoic acid

: 10167-97-2
2-amino-5-methoxypyridine

: 3-((13S,15R)-4-fluoro-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl)-N-(5-methoxypyridin-2-yl)propanamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 50℃; for 2h;	80%

: 100-41-4
ethylbenzene

: 10167-97-2
2-amino-5-methoxypyridine

: 869583-76-6
6-methoxy-2-phenylimidazolo[1,2-a]pyridine

Conditions

Conditions	Yield
Stage #1: ethylbenzene With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In water; ethyl acetate at 65℃; for 1.5h; Stage #2: 2-amino-5-methoxypyridine With sodium carbonate In water at 80℃;	80%

: 10167-97-2
2-amino-5-methoxypyridine

: C6H8N2O2

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In acetone at 0 - 20℃; for 12.5h;	80%

: 10167-97-2
2-amino-5-methoxypyridine

: 635-93-8
5-chlorosalicyclaldehyde

: (E)-4-chloro-2-(((5-methoxypyridin-2-yl)imino)methyl)phenol

Conditions

Conditions	Yield
In ethanol for 6h; Reflux;	79%

: 32807-28-6
Methyl 4-chloroacetoacetate

: 10167-97-2
2-amino-5-methoxypyridine

: 1434288-35-3
2-(chloromethyl)-7-methoxy-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With polyphosphoric acid at 100℃; for 2h; Sealed tube;	78%

: 107-20-0
2-chloroethanal

: 10167-97-2
2-amino-5-methoxypyridine

: 6-methoxyimidazo[1,2-a]pyridine hydrochloride

Conditions

Conditions	Yield
In ethanol; water Reflux;	77%

: 672-13-9
2-hydroxy-5-methoxybenzaldehyde

: 10167-97-2
2-amino-5-methoxypyridine

: (E)-4-methoxy-2-(((5-methoxypyridin-2-yl)imino)methyl)phenol

Conditions

Conditions	Yield
In ethanol for 6h; Reflux;	77%

: (3-bromo-2-oxopropyl)((tert-butyldiphenylsilyl)imino)(phenyl)-λ6-sulfanone

: 10167-97-2
2-amino-5-methoxypyridine

: ((tert-butyldiphenylsilyl)imino)((6-methoxyimidazo[1,2-a] pyridin-3-yl)methyl)(phenyl)-λ6-sulfanone

Conditions

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane at 90℃; for 15h; Sealed tube; Inert atmosphere;	76%

: 504-02-9
1,3-cylohexanedione

: 10167-97-2
2-amino-5-methoxypyridine

: 3-((5-methoxypyridin-2-yl)amino)cyclohex-2-en-1-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In water; toluene for 4h; Dean-Stark; Reflux; Inert atmosphere;	76%

: 30718-17-3
trimethylsilylmethyl isocyanide

: 123-08-0
4-hydroxy-benzaldehyde

: 10167-97-2
2-amino-5-methoxypyridine

: 4-(6-methoxy-3-(((trimethylsilyl)methyl)amino)imidazo[1,2-a]pyridin-2-yl)phenol

Conditions

Conditions	Yield
With hydrogenchloride In ethanol at 130℃; for 0.833333h; Flow reactor; Green chemistry;	76%

...Expand

: 1227281-44-8
3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-methoxy-4-oxobutanoic acid

: 10167-97-2
2-amino-5-methoxypyridine

: methyl 2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-[(5-methoxypyridin-2-yl)carbamoyl]propanoate

Conditions

Conditions	Yield
Stage #1: 3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-methoxy-4-oxobutanoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.333333h; Stage #2: 2-amino-5-methoxypyridine In N,N-dimethyl-formamide at 20℃; for 16h;	75%

: 455-14-1
4-trifluoromethylphenylamine

: 1227281-44-8
3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-methoxy-4-oxobutanoic acid

: 10167-97-2
2-amino-5-methoxypyridine

: methyl 2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-[(5-methoxypyridin-2-yl)carbamoyl]propanoate

Conditions

Conditions	Yield
Stage #1: 4-trifluoromethylphenylamine; 3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-methoxy-4-oxobutanoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.333333h; Stage #2: 2-amino-5-methoxypyridine In N,N-dimethyl-formamide at 20℃; for 16h;	75%

...Expand

: (R)-4-((8-chloro-2,5-dioxo-3-(pyridin-2-ylmethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-4(5H)-yl)methyl)-2-fluorobenzoic acid

: 10167-97-2
2-amino-5-methoxypyridine

: (R)-4-((8-Chloro-2,5-dioxo-3-(pyridin-2-ylmethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-4(5H)-yl)methyl)-2-fluoro-N-(5-methoxypyridin-2-yl)benzamide

Conditions

Conditions	Yield
Stage #1: (R)-4-((8-chloro-2,5-dioxo-3-(pyridin-2-ylmethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-4(5H)-yl)methyl)-2-fluorobenzoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In 1-methyl-pyrrolidin-2-one for 0.25h; Inert atmosphere; Microwave irradiation; Stage #2: 2-amino-5-methoxypyridine In 1-methyl-pyrrolidin-2-one at 80℃; for 0.0833333h; Inert atmosphere; Microwave irradiation;	75%

Yield

Stage #1: (R)-4-((8-chloro-2,5-dioxo-3-(pyridin-2-ylmethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-4(5H)-yl)methyl)-2-fluorobenzoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In 1-methyl-pyrrolidin-2-one for 0.25h; Inert atmosphere; Microwave irradiation;
Stage #2: 2-amino-5-methoxypyridine In 1-methyl-pyrrolidin-2-one at 80℃; for 0.0833333h; Inert atmosphere; Microwave irradiation;

75%

: 1-(bromomethyl)-4-ethynylbenzene

: 10167-97-2
2-amino-5-methoxypyridine

: 2-(4-bromomethylphenyl)-6-methoxyimidazo[1,2-a]pyridine

Conditions

Conditions	Yield
With silver carbonate In 1,4-dioxane at 100℃; for 10h; Schlenk technique; Inert atmosphere;	75%

: 24115-90-0
2-nitro-3-benzyloxybenzoyl chloride

: 10167-97-2
2-amino-5-methoxypyridine

: 3-benzyloxy-N-(5-methoxy-2-pyridyl)-2-nitrobenzamide

Conditions

Conditions	Yield
With pyridine at 20℃; for 20h;	74%

2-Amino-5-methoxypyridine Chemical Properties

Following is the structure of 2-Amino-5-methoxypyridine (CAS NO.10167-97-2):

Molecular Formula: C₆H₈N₂O
Molecular Weight: 124.14
Index of Refraction: 1.56
Molar Refractivity: 35.25 cm³
Molar Volume: 108.9 cm³
Density: 1.139 g/cm³
Flash Point: 106 °C
Surface Tension: 46.1 dyne/cm
Enthalpy of Vaporization: 48.9 kJ/mol
Boiling Point: 251.6 °C at 760 mmHg
Vapour Pressure: 0.0202 mmHg at 25 °C
Appearance of 2-Amino-5-methoxypyridine (CAS NO.10167-97-2): Dark Red Oil
Product Categories of 2-Amino-5-methoxypyridine (CAS NO.10167-97-2): Chemical Amines; Amines; Heterocycles
SMILES: O(c1cnc(N)cc1)C
InChI: InChI=1/C6H8N2O/c1-9-5-2-3-6(7)8-4-5/h2-4H,1H3,(H2,7,8)
InChIKey: XJKJHILCYUUVSJ-UHFFFAOYAQ

2-Amino-5-methoxypyridine Specification

2-Amino-5-methoxypyridine , its cas register number is 10167-97-2. It also can be called 5-Methoxy-pyridin-2-ylamine .

Product Name

5-METHOXY-PYRIDIN-2-YLAMINE

Synthetic route

2-Amino-5-methoxypyridine Chemical Properties

2-Amino-5-methoxypyridine Specification

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