5-Amino-2-methoxypyridine supplier

Name
5-Amino-2-methoxypyridine
EINECS 229-612-8
CAS No. 6628-77-9
Article Data35
CAS DataBase
Density 1.139 g/cm³
Solubility slightly soluble in water
Melting Point 29-31 °C(lit.)
Formula C₆H₈N₂O
Boiling Point 264.8 °C at 760 mmHg
Molecular Weight 124.142
Flash Point 109.5 °C
Transport Information
Appearance yellow-brown or red to very dark red liquid
Safety 26-37/39-36
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Pyridine, 5-amino-2-methoxy-;6-methoxypyridin-3-amine;6-Methoxy-3-pyridylamine;3-Pyridinamine, 6-methoxy-;5-22-11-00408 (Beilstein Handbook Reference);2-methoxy-5-aminopyridine;
PSA 48.14000
LogP 1.25360

Synthetic route

: 5446-92-4
2-methoxy-5-nitropyridine

: 6628-77-9
6-methoxy-pyridin-3-ylamine

Conditions

Conditions	Yield
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h;	100%
With cyclohexa-1,4-diene; 5%-palladium/activated carbon In methanol at 120℃; for 0.0833333h; Microwave irradiation;	99%
With iron; calcium chloride In ethanol for 2h; Heating;	97%

: 13472-85-0
2-methoxy-5-bromopyridine

: 6628-77-9
6-methoxy-pyridin-3-ylamine

Conditions

Conditions	Yield
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 80℃; for 23h; Inert atmosphere;	95%
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; Sealed tube;	86%
Multi-step reaction with 2 steps 1.1: copper(l) iodide; potassium carbonate; L-proline / dimethyl sulfoxide / Inert atmosphere 1.2: 80 °C / Inert atmosphere 2.1: palladium on activated charcoal; ammonium formate / methanol / Reflux View Scheme

: 96530-77-7
2-methoxy-5-nitropyridine N-oxide

: 6628-77-9
6-methoxy-pyridin-3-ylamine

Conditions

Conditions	Yield
With iron In acetic acid	89%

: 4548-45-2
2-chloro-5-nitropyridine

: 6628-77-9
6-methoxy-pyridin-3-ylamine

Conditions

Conditions	Yield
With sodium hydroxide anschliessendes Hydrieren an Palladium/CaCO3;
Multi-step reaction with 2 steps 2: iron-powder; acetic acid; aqueous methanol View Scheme
Multi-step reaction with 2 steps 2: platinum; ethanol / Hydrogenation View Scheme

: 2-bromo-6-methoxy-3-nitropyridine

: 6628-77-9
6-methoxy-pyridin-3-ylamine

Conditions

Conditions	Yield
With hydrogen; Lindlar's catalyst In ethanol

: 7150-23-4
6-methyoxy-3-pyridinecarboxamide

: 6628-77-9
6-methoxy-pyridin-3-ylamine

Conditions

Conditions	Yield
With sodium hydroxide; bromine In tetrahydrofuran at 5 - 70℃; Hoffmann rearrangement;

: 4548-45-2
2-chloro-5-nitropyridine

potassium-salt of/the/ 4-acetylamino-benzenesulfinic acid: potassium-salt of/the/ 4-acetylamino-benzenesulfinic acid

: 6628-77-9
6-methoxy-pyridin-3-ylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / NaH / tetrahydrofuran / 1 h / Ambient temperature 2: hydrogen / 5 percent Pd/C / methanol / 760 Torr / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 99 percent / 1.) sodium metal / 24 h / 70 °C / Heating 2: cyclohexene / 5percent Pd-C / ethanol / Heating View Scheme

: 40473-07-2
6-bromo-2-methoxypyridine

: 6628-77-9
6-methoxy-pyridin-3-ylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / potassium nitrate, concd. H2SO4 / 2 h / 75 °C 2: H2 / 5percent Pd/CaCO3 / ethanol View Scheme

: 28080-54-8
2-iodo-5-nitropyridine

: 6628-77-9
6-methoxy-pyridin-3-ylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium methylate; methanol 2: SnCl2; HCl; diethyl ether View Scheme

: 342793-48-0
N-benzyl-6-methoxypyridin-3-amine

: 6628-77-9
6-methoxy-pyridin-3-ylamine

Conditions

Conditions	Yield
With palladium on activated charcoal; ammonium formate In methanol Reflux;

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 6628-77-9
6-methoxy-pyridin-3-ylamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride; sodium nitrite / water / 0.67 h / 0 - 6 °C 2: trichlorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C / Reflux 3: methanol / 1 h / Reflux 4: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 60 °C / 7500.75 Torr View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / Reflux 2: trichlorophosphate / N,N-dimethyl-formamide / Reflux 3: Reflux 4: iron; acetic acid / ethanol / Reflux View Scheme

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 87-13-8
diethyl 2-ethoxymethylenemalonate

: 53241-90-0
diethyl {[(6-methoxypyridin-3-yl)amino]methylidene}propanedioate

Conditions

Conditions	Yield
In ethanol for 4h; Heating / reflux;	100%
In ethanol for 4h; Heating / reflux;	100%
In ethanol for 4h; Heating / reflux;	100%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 135795-46-9
2-bromo-6-methoxy-pyridin-3-ylamine

Conditions

Conditions	Yield
With bromine; sodium acetate In acetic acid at 20℃; for 0.5h;	100%
With hydrogen bromide; dihydrogen peroxide In water at 5 - 20℃;	97%
With bromine; sodium acetate In acetic acid for 0.333333h;	60%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 3282-30-2
pivaloyl chloride

: 227180-19-0
2,2-dimethyl-N-<5-(2-methoxypyridinyl)>propanamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 0.5h; Cooling with ice;	100%
With triethylamine In dichloromethane 0 deg C, 10 min; RT, 2h;	99%
With triethylamine In dichloromethane at 0 - 20℃; for 2.16667h;

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 6-methoxypyridin-3-diazonium tetrafluoroborate

Conditions

Conditions	Yield
With tetrafluoroboric acid; sodium nitrite In ethanol; water at 0℃; for 3h;	100%
With tetrafluoroboric acid; sodium nitrite In ethanol; water at 0℃; for 3h; Product distribution / selectivity;	91%
With tetrafluoroboric acid; sodium nitrite In ethanol; water at 0℃; for 2h;	91%
Stage #1: 6-methoxy-pyridin-3-ylamine With boron trifluoride diethyl etherate In tetrahydrofuran for 0.0833333h; Cooling with ice; Stage #2: With tert.-butylnitrite In tetrahydrofuran at 0℃;	80%
With tetrafluoroboric acid; sodium nitrite at 5℃;	72%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 5662-95-3
3,3-tetramethylene glutaric anhydride

: 8-(6-methoxypyridin-3-yl)-8-azaspiro[4.5]decane-7,9-dione hydrochloride

Conditions

Conditions	Yield
Stage #1: 6-methoxy-pyridin-3-ylamine; 3,3-tetramethylene glutaric anhydride In dichloromethane at 20℃; for 3h; Stage #2: With thionyl chloride In dichloromethane at 20℃; for 3.5h;	100%
Stage #1: 6-methoxy-pyridin-3-ylamine; 3,3-tetramethylene glutaric anhydride In dichloromethane at 20℃; for 3h; Stage #2: With thionyl chloride In dichloromethane at 20℃; for 3.5h;	100%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 2719-27-9
cyclohexanylcarbonyl chloride

: 548763-48-0
cyclohexanecarboxylic acid (6-methoxy-pyridin-3-yl)-amide hydrochloride

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether	100%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 23860-35-7
cyclohexylacetic acid chloride

: 548763-51-5
2-Cyclohexyl-N-(6-methoxy-pyridin-3-yl)-acetamide hydrochloride

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether	100%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 15568-85-1
5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

: 25063-69-8
5-[[(6-methoxypyridin-3-yl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions

Conditions	Yield
In isopropyl alcohol Heating;	100%
In isopropyl alcohol at 70℃; for 0.5h;
In isopropyl alcohol for 1h; Heating / reflux;

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 5231-87-8
3,4-diethoxy-3-cyclobuten-1,2-dione

: 1018682-14-8
C12H12N2O4

Conditions

Conditions	Yield
In methanol; water for 0.5h; Heating;	100%

: 288-36-8
1,2,3-triazole

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 864178-16-5
C12H13ClN2O2

A: 5-[3-(4-ethoxy-3-methyl-phenyl)-5-[1,2,3]triazol-2-ylmethyl-[1,2,4]triazol-4-yl]-2-methoxy-pyridine

B: 5-[3-(4-ethoxy-3-methyl-phenyl)-5-[1,2,3]triazol-1-ylmethyl-[1,2,4]triazol-4-yl]-2-methoxy-pyridine

Conditions

Conditions	Yield
Stage #1: 1,2,3-triazole; C12H13ClN2O2 With potassium carbonate In DMF (N,N-dimethyl-formamide); acetonitrile for 18h; Stage #2: 6-methoxy-pyridin-3-ylamine; toluene-4-sulfonic acid In xylene at 140℃; for 6h;	A 100% B 100%

...Expand

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 52023-93-5
5-isothiocyanato-2-methoxypyridine

Conditions

Conditions	Yield
In tetrahydrofuran	100%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 6834-42-0
3-methoxyphenylacetic acid chloride

: 295318-90-0
2-(3-methoxyphenyl)-N-{2-methoxy(5-pyridyl)}acetamide

Conditions

Conditions	Yield
	99%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 815-17-8
trimethylpyruvic acid

: 1028253-88-4
C12H18N2O3

Conditions

Conditions	Yield
Stage #1: 6-methoxy-pyridin-3-ylamine; trimethylpyruvic acid With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 24h; Stage #2: With water; ammonium chloride In 1,2-dichloro-ethane	99%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 4-(chlorosulfonyl)benzenesulfonyl fluoride

: C12H11FN2O5S2

Conditions

Conditions	Yield
With pyridine In chloroform at 20℃; for 48h; chemoselective reaction;	99%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 607-68-1
2,4-dichloroquinazoline

: 2-chloro-N-(6-methoxypyridin-3-yl)quinazolin-4-amine

Conditions

Conditions	Yield
With sodium acetate In tetrahydrofuran; water at 60℃; for 0.75h;	98%
With sodium acetate In tetrahydrofuran; water at 60℃; for 0.75h;	98%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 24424-99-5
di-tert-butyl dicarbonate

: 183741-80-2
tert-butyl N-(6-methoxypyridin-3-yl)carbamate

Conditions

Conditions	Yield
In 1,4-dioxane Reflux;	97%
In 1,4-dioxane	96%
In 1,4-dioxane for 0.5h; Heating;	94%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 1147550-11-5
ammonium thiocyanate

: 13797-77-8
5-methoxythiazolo[5,4-b]pyridin-2-amine

Conditions

Conditions	Yield
Stage #1: 6-methoxy-pyridin-3-ylamine; ammonium thiocyanate In acetonitrile at 20℃; for 0.166667h; Stage #2: With benzyltrimethylazanium tribroman-2-uide In acetonitrile at 20℃;	97%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 710324-65-5
3-(2-Chloro-4-phenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester

: 710324-66-6
3-[2-(6-Methoxy-pyridin-3-ylamino)-4-phenylamino-pyrimidin-5-yl]-2-(4-methoxy-phenyl)-propionic acid methyl ester

Conditions

Conditions	Yield
In ethyl acetate at 110℃; for 4h;	96.8%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 1885-14-9
phenyl chloroformate

: 102671-59-0
(6-methoxy-pyridin-3-yl)-carbamic acid phenyl ester

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 0 - 20℃; for 12h;	96%
With pyridine In tetrahydrofuran at 0 - 20℃;	96%
With pyridine In tetrahydrofuran at 0 - 20℃;	96%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 40134-18-7
methyl 2-chloropyridine-3-carboxylate

: 1239165-03-7
methyl 2-(6-methoxy-3-pyridinyl)aminonicotinate

Conditions

Conditions	Yield
With caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 90℃; for 72h;	96%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 17341-93-4
2,2,2-Trichloroethyl chloroformate

: 887624-73-9
2,2,2-trichloroethyl (6-methoxypyridin-3-yl)carbamate

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 0℃; for 0.5h;	95.4%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 2033-24-1
cycl-isopropylidene malonate

: 122-51-0
orthoformic acid triethyl ester

: 25063-69-8
5-[[(6-methoxypyridin-3-yl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions

Conditions	Yield
In ethanol for 1h; Reflux; Large scale;	95%
In ethanol for 1h; Reflux; Large scale;	95%
In ethanol for 1h; Reflux; Large scale;	95%

...Expand

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 160664-95-9
5-hydrazinyl-2-methoxy pyridine

Conditions

Conditions	Yield
Stage #1: 6-methoxy-pyridin-3-ylamine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With hydrogenchloride; tin(II) chloride dihdyrate In water at 0℃; for 2.5h; Stage #3: With potassium hydroxide In water	95%
Stage #1: 6-methoxy-pyridin-3-ylamine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With hydrogenchloride; tin(II) chloride dihdyrate In water at 0℃; for 2.5h;	95%
Stage #1: 6-methoxy-pyridin-3-ylamine With hydrogenchloride; water; sodium nitrite at 0 - 5℃; Stage #2: With hydrogenchloride; tin(ll) chloride at -25 - -20℃; for 2.5h; Stage #3: With water; potassium hydroxide In dichloromethane at 0 - 5℃; for 1.5h;	70%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 2-(4-(2-bromobenzoyl)phenoxy)acetic acid

: 2-[4-(2-bromobenzoyl)phenoxy]-N-(6-methoxypyridin-3-yl)acetamide

Conditions

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	94%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 787564-31-2
2-[(5-fluoropyridine-2-carbonyl)amino]malonic acid diethyl ester

: 787564-29-8
5-(5-fluoro-2-pyridyl)-1-(6-methoxy-3-pyridyl)-1H-1,2,4-triazole-3-carboxylic acid sodium salt

Conditions

Conditions	Yield
Stage #1: 6-methoxy-pyridin-3-ylamine With hydrogenchloride; acetic acid; sodium nitrite In water at 0℃; for 0.25h; Stage #2: 2-[(5-fluoropyridine-2-carbonyl)amino]malonic acid diethyl ester With potassium carbonate In water; acetone at -15 - 0℃; for 2.5h; Stage #3: With sodium methylate In methanol at 20℃; for 60h;	93%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: tert-butyl 6-oxo-3-azabicyclo[3.1.1]heptane-3-carboxylate

: tert-butyl 6-((6-methoxypyridin-3-yl)amino)-3-azabicyclo[3.1.1]heptane-3-carboxylate

Conditions

Conditions	Yield
With nido-decaborane In methanol; trans-1,2-dichloroethylene at 20℃; Inert atmosphere;	93%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 102368-13-8
1,1'-Thiocarbonyldi-2(1H)-pyridone

: 52023-93-5
5-isothiocyanato-2-methoxypyridine

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 3.5h;	92%

: 6628-77-9
6-methoxy-pyridin-3-ylamine

: 319-03-9
4-fluorophthalic anhydride

: 5-fluoro-2-(6-methoxypyridin-3-yl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With sodium acetate; acetic acid at 118℃; for 2h;	91.4%

5-Amino-2-methoxypyridine Specification

The 5-Amino-2-methoxypyridine with cas registry number of 6628-77-9 belongs to the classes in Pyridine; Pyridines, Pyrimidines, Purines and Pteredines; Pyridine series; Pyridines derivates; Pyridines; Boronic Acid; C6; Heterocyclic Building Blocks; Amino-pyridine series. Its EINECS registry number is 229-612-8. This chemical is also known as Pyridine, 5-amino-2-methoxy- and 6-Methoxy-3-pyridylamine which is also its IUPAC name.

Physical properties about this chemical are: (1)ACD/LogP: 0.47; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.46; (4)ACD/LogD (pH 7.4): 0.47; (5)ACD/BCF (pH 5.5): 1.29; (6)ACD/BCF (pH 7.4): 1.34; (7)ACD/KOC (pH 5.5): 41.42; (8)ACD/KOC (pH 7.4): 42.98; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.56 ; (13)Molar Refractivity: 35.25 cm³; (14)Molar Volume: 108.9 cm³; (15)Surface Tension: 46.1 dyne/cm; (16)Density: 1.139 g/cm³; (17)Flash Point: 109.5 °C; (18)Enthalpy of Vaporization: 50.27 kJ/mol; (19)Boiling Point: 264.8 °C at 760 mmHg; (20)Vapour Pressure: 0.00951 mmHg at 25°C.

Preparation of 5-Amino-2-methoxypyridine: this chemical can be made by 2-methoxy-5-nitro-pyridine by using reagents Me₃SiSNa and 1,3-dimethyl2-imidazolidinone under the reaction temperature 185 ℃. The reaction time is 3 hours. The yield is 70%.

Uses of 5-Amino-2-methoxypyridine: it can used to prepare 3-amino-2-bromo-6-methoxypyridine by using reagents NaOAc and Br₂, solvent Acetic acid with reaction time 20 min. The yield is 60%.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed and irritating to eyes, respiratory system and skin. Wear suitable protective clothing, gloves and eye/face protection during using it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: COC1=NC=C(C=C1)N;
(2)InChI: InChI=1S/C6H8N2O/c1-9-6-3-2-5(7)4-8-6/h2-4H,7H2,1H3;
(3)InChIKey: UUVDJIWRSIJEBS-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	1250mg/kg (1250mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 89, Pg. 153, 1947.

Product Name

5-Amino-2-methoxypyridine

Synthetic route

5-Amino-2-methoxypyridine Specification

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