848774-90-3

Basic information

• Product Name: 2-PyridineMethanol,3,6-diMethyl-
• Synonyms: 2-PyridineMethanol,3,6-diMethyl-;3,6-dimethyl-2-Pyridinemethanol
• CAS NO: 848774-90-3
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.17904
• Mol File: 848774-90-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 239.4 °C at 760 mmHg
• Flash Point: 98.6 °C
• Appearance: /
• Density: 1.063 g/cm³
• Vapor Pressure: 0.0219mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 2-PyridineMethanol,3,6-diMethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PyridineMethanol,3,6-diMethyl-(848774-90-3)
• EPA Substance Registry System: 2-PyridineMethanol,3,6-diMethyl-(848774-90-3)

Safety Data

• Hazardous Substances Data: 848774-90-3(Hazardous Substances Data)

Usage

General Description

2-Pyridinemethanol, 3,6-dimethyl- is a chemical compound with the molecular formula C9H13NO. It is a white to beige solid substance that is soluble in water and organic solvents. 2-Pyridinemethanol,3,6-dimethyl- is used in the synthesis of pharmaceuticals and agrochemicals. It is also commonly used in the manufacturing of perfumes and flavoring agents. Additionally, 2-Pyridinemethanol, 3,6-dimethyl- is utilized as an intermediate in the production of other compounds such as pesticides and herbicides. This chemical is known to have potential health hazards if inhaled or ingested, and should be handled with caution in a well-ventilated area with appropriate personal protective equipment.

InChI:InChI=1/C8H11NO/c1-6-3-4-7(2)9-8(6)5-10/h3-4,10H,5H2,1-2H3

Synthetic route

3,6-dimethyl-2-pyridinecarbonitrile (68164-77-2) → (3,6-dimethylpyridin-2-yl)methanol (848774-90-3)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal under 1551.44 Torr; for 2h;	57%

2,5-dimethylpyridine N-oxide (4986-05-4) → (3,6-dimethylpyridin-2-yl)methanol (848774-90-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: CH2Cl2 / 0.42 h / 20 °C 2: 9.72 g / Et2NCOCl / CH2Cl2 / 96 h / 20 °C 3: 57 percent / H2; aq. HCl / Pd/C / 2 h / 1551.44 Torr View Scheme

2-cyano-3,6-dimethylpyridine 1-oxide (892665-90-6) → (3,6-dimethylpyridin-2-yl)methanol (848774-90-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 9.72 g / Et2NCOCl / CH2Cl2 / 96 h / 20 °C 2: 57 percent / H2; aq. HCl / Pd/C / 2 h / 1551.44 Torr View Scheme

6-chloro-3-phenyl-7,8,9,10-tetrahydro-(7,10-ethano)-1,2,4-triazolo[3,4-a]phthalazine (202931-56-4) + (3,6-dimethylpyridin-2-yl)methanol (848774-90-3) → C25H25N5O

Conditions	Yield
Stage #1: (3,6-dimethylpyridin-2-yl)methanol With sodium hydride In N,N-dimethyl-formamide at 20℃; Stage #2: 6-chloro-3-phenyl-7,8,9,10-tetrahydro-(7,10-ethano)-1,2,4-triazolo[3,4-a]phthalazine In N,N-dimethyl-formamide at 20℃;	54%

Upstream product

• 892665-90-6 2-cyano-3,6-dimethylpyridine 1-oxide 
• 4986-05-4 2,5-dimethylpyridine N-oxide 
• 68164-77-2 3,6-dimethylpyridine-2-carbonitrile 

Relevant articles and documents

Discovery of functionally selective 7,8,9,10-tetrahydro-7,10-ethano-1,2,4- triazolo[3,4-a]phthalazines as GABAA receptor agonists at the α3 subunit

We have previously identified the 7,8,9,10-tetrahydro-7,10-ethano-1,2,4- triazolo[3,4-a]phthalazine (1) as a potent partial agonist for the 0.3 receptor subtype with 5-fold selectivity in binding affinity over α1. This paper describes a detailed investigation of the substituents on this core structure at both the 3- and 6-positions. Despite evaluating a wide range of groups, the maximum selectivity that could be achieved in terms of affinity for the α3 subtype over the α1 subtype was 12-fold (for 57). Although most analogues showed no selectivity in terms of efficacy, some did show partial agonism at α1 and antagonism at α3 (e.g., 25 and 75). However, two analogues tested (93 and 96), both with triazole substituents in the 6-position, showed significantly higher efficacy for the α3 subtype over the α1 subtype. This was the first indication that selectivity in efficacy in the required direction could be achieved in this series.