109345-94-0

Basic information

• Product Name: 5-METHOXY-PYRIDIN-3-OL
• Synonyms: 3-HYDROXY-5-METHOXYPYRIDINE;5-METHOXY-PYRIDIN-3-OL;3-Pyridinol,5-methoxy-(9CI);5-Methoxypyridin-3-ol, 5-Hydroxypyridin-3-yl methyl ether;5-Methoxy-pyridin-3-ol
• CAS NO: 109345-94-0
• Molecular Formula: C₆H₇NO₂
• Molecular Weight: 125.13
• Product Categories: PYRIDINE
• Mol File: 109345-94-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 147.5-148.5 °C(Solv: ethanol (64-17-5))
• Boiling Point: 346.72 °C at 760 mmHg
• Flash Point: 163.491 °C
• Appearance: /
• Density: 1.191 g/cm³
• Vapor Pressure: 2.82E-05mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.93±0.10(Predicted)
• CAS DataBase Reference: 5-METHOXY-PYRIDIN-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-PYRIDIN-3-OL(109345-94-0)
• EPA Substance Registry System: 5-METHOXY-PYRIDIN-3-OL(109345-94-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 109345-94-0(Hazardous Substances Data)

Usage

Chemical Properties

Off white powder

Uses

5-Methoxypyridin-3-ol is patented as a reagent to prepare various compounds as nicotinic receptor ligands.

InChI:InChI=1/C6H7NO2/c1-9-6-2-5(8)3-7-4-6/h2-4,8H,1H3

Upstream product

• 50720-12-2 3-bromo-5-methoxypyridine 
• 445264-60-8 3-methoxy-5-pyridineboronic acid pinacol ester 
• 64436-92-6 3-amino-5-methoxypyridine 
• 50866-56-3 1-(benzyl)piperidin-3,5-dione 
• 50720-06-4 1-benzyl-3-methoxy-5-oxo-3,4-dehydropiperidine 
• 109345-93-9 1-benzyl-5-methoxy-3-oxidopyridinium betaine 

Downstream Products

• 1289038-89-6 3-hydroxy-5-methoxypyridin-4-carbaldehyde 
• 672957-96-9 3-hydroxy-5-methoxy-2-pyridinecarboxylic acid 
• 29681-46-7 methyl 5-methoxypyridine-3-carboxylate 
• 20826-03-3 5-methoxypyridine-3-carboxylic acid 
• 109345-96-2 1-amino-3-hydroxy-5-methoxypyridinium mesitylenesulfonate 

Relevant articles and documents

INHIBITORS OF THE KYNURENINE PATHWAY

The present application provides novel inhibitors of indoleamine 2,3-dioxygenase-1 and/or indoleamine 2,3-dioxygenase-2 and/or tryptophan 2,3-dioxygenase, metabolites thereof, and phannaceutically acceptable salts or prodrugs thereof. Also provided are methods for preparing these compounds. A therapeutically effective amount of one or more of the compounds of formula (I) is useful in treating diseases resulting from dysregulation of the kynurenine pathway. Compounds of formula (I) act by inhibiting the enzymatic activity or expression of indoleamine 2,3-dioxygenase-1 and/or indoleamine 2,3-dioxygenase-2 and/or tryptophan 2,3-dioxygenase.

PHARMACEUTICAL COMPOSITIONS AND METHODS FOR USE

Patients susceptible to or suffering from conditions and disorders, such as central nervous system disorders, are treated by administering to a patient in need thereof aryloxyalkylamines, including pyridyloxylalkylamines and phenoxyalkylamines. Exemplary compounds include dimethyl(2-(3-pyridyloxy)ethylamine, dimethyl(4-(3-pyridyloxy)butyl)amine, 2-(3-pyridyloxy)ethylamine, 4-(3-pyridyloxy)butylamine, methyl(3-(5-methoxy-3-pyridyloxy)propyl)amine, ethyl(3-(3-pyridyloxy)propyl)amine, methyl(2-(3-pyridyloxy)ethyl)amine, methyl(3-(6-methyl(3-pyridyloxy))propyl)amine, (3-(3-methoxyphenoxy)propyl)methylamine, (3-(5-chloro(3-pyridyloxy))-1-methylpropyl)methylamine, dimethyl(3-(3-pyridyloxy)propyl)amine, 3-(3-pyridyloxy)propylamine, methyl(4-(3-pyridyloxy)butyl)amine, 3-(5-chloro-3-pyridyloxy)propyl amine, methyl(3-(5-isopropoxy-3-pyridyloxy)propyl)amine, (3-(5-chloro(3-pyridyloxy))propyl) methylamine, methyl(3-(5-(phenylmethoxy)(3-pyridyloxy))propyl)amine, methyl(3-(2-methyl(3-pyridyloxy))propyl)amine, (methylethyl)(3-(3-pyridyloxy)propyl)amine, benzyl(3-(3-pyridyloxy)propyl)amine, cyclopropyl(3-(3-pyridyloxy)-propyl)amine, methyl(1-methyl-3-(3-pyridyloxy)propyl)amine, methyl(3-(3-nitrophenoxy)propyl)amine, 1-(3-chloropropoxy)-3-nitrobenzene, (3-(3-aminophenoxy)propyl)methylamine,dimethyl (3-(3-(methylamino)-propoxy)phenyl)amine, methyl(3-tricyclo[7.3.1.0]tridec-2-yloxypropyl)amine, (3-benzo[3,4-d]1,3-dioxolan-5-yloxypropyl)methylamine, 3-(4-piperidinyloxy)pyridine and 3-((3S)-3-pyrrolidinyloxy)pyridine.

SYNTHESIS AND 1,3-DIPOLAR CYCLOADDITION OF 3-HYDROXY-5-METHOXY-PYRIDINIUM N-IMINE

The synthesis and 1,3-dipolar cycloaddition of 3-hydroxy-5-methoxypyridinium N-imine (12) is described.Compound 12 was found to undergo 1,3-dipolar cycloaddition reaction with ethyl propiolate to give ethyl 8-amino-4-methoxy-2-oxo-8-azabicyclooct-3,6-diene-6-carboxylate (13) and ethyl 4-hydroxy-6-methoxypyrazopyridine-3-carboxylate (14).