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6628-77-9

Basic Information
CAS No.: 6628-77-9
Name: 5-Amino-2-methoxypyridine
Article Data: 35
Cas Database
Molecular Structure:
Molecular Structure of 6628-77-9 (5-Amino-2-methoxypyridine)
Formula: C6H8N2O
Molecular Weight: 124.142
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;
EINECS: 229-612-8
Density: 1.139 g/cm3
Melting Point: 29-31 °C(lit.)
Boiling Point: 264.8 °C at 760 mmHg
Flash Point: 109.5 °C
Solubility: slightly soluble in water
Appearance: yellow-brown or red to very dark red liquid
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36/37/38
Safety: 26-37/39-36
Transport Information: N/A
PSA: 48.14000
LogP: 1.25360
Synthetic route
5446-92-4

2-methoxy-5-nitropyridine

6628-77-9

6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With iron In acetic acid89%
4548-45-2

2-chloro-5-nitropyridine

6628-77-9

6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
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
ConditionsYield
With hydrogen; Lindlar's catalyst In ethanol
7150-23-4

6-methyoxy-3-pyridinecarboxamide

6628-77-9

6-methoxy-pyridin-3-ylamine

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