60588-81-0

Basic information

• Product Name: (3-CHLOROPYRIDIN-2-YL)METHANOL
• Synonyms: (3-CHLOROPYRIDIN-2-YL)METHANOL;3-Chloro-2-pyridineMethanol;3-Chloro-2-hydroxymethylpyridine;3-Chloropyridine-2-methanol;(3-Chloro-2-pyridyl)methanol
• CAS NO: 60588-81-0
• Molecular Formula: C₆H₆ClNO
• Molecular Weight: 143.57
• Mol File: 60588-81-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 234.897°C at 760 mmHg
• Flash Point: 95.862°C
• Appearance: /
• Density: 1.324g/cm³
• Vapor Pressure: 0.028mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 12.80±0.10(Predicted)
• CAS DataBase Reference: (3-CHLOROPYRIDIN-2-YL)METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (3-CHLOROPYRIDIN-2-YL)METHANOL(60588-81-0)
• EPA Substance Registry System: (3-CHLOROPYRIDIN-2-YL)METHANOL(60588-81-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 60588-81-0(Hazardous Substances Data)

Usage

General Description

(3-Chloropyridin-2-yl)methanol is a chemical compound with the molecular formula C6H6ClNO. It is a derivative of pyridine, a six-membered ring compound containing one nitrogen atom. (3-CHLOROPYRIDIN-2-YL)METHANOL is a white to off-white powder that is used as a reagent in organic synthesis and pharmaceutical research. It is an important intermediate in the manufacture of various pharmaceuticals and agrochemicals. Its structure and properties make it a versatile building block for the synthesis of more complex molecules, and it is widely used in the development of new drugs and crop protection products.

InChI:InChI=1/C6H6ClNO/c7-5-2-1-3-8-6(5)4-9/h1-3,9H,4H2

Upstream product

• 124425-86-1 Acetic acid 3-chloro-pyridin-2-ylmethyl ester 
• 57266-69-0 3-chloropyridine-2-carboxylic acid 
• 72093-03-9 3-chloro-2-methylpyridine 
• 52313-57-2 3-Chlor-2-picolin-1-oxid 
• 38180-46-0 3-chloro-2-cyanopyridine 
• 52378-63-9 3-amino-2-hydroxy-methylpyridine 
• 626-60-8 3-Chloropyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 96424-68-9 2-bromo-3-chloropyridine 

Downstream Products

• 185315-53-1 3-chloro-2-(chloromethyl)pyridine 
• 206181-90-0 3-chloropyridine-2-carboxaldehyde 

Relevant articles and documents

Asymmetric Synthesis of Adjacent Tri- and Tetrasubstituted Carbon Stereocenters: Organocatalytic Aldol Reaction of an Hydantoin Surrogate with Azaarene 2-Carbaldehydes

A bifunctional amine/squaramide catalyst promoted direct aldol addition of an hydantoin surrogate to pyridine 2-carbaldehyde N-oxides to afford adducts bearing two vicinal tertiary/quaternary carbons in high diastereo- and enantioselectivity (d.r. up to >20:1; ee up to 98 %) is reported. Acid hydrolysis of adducts followed by reduction of the N-oxide group yields enantiopure carbinol-tethered quaternary hydantoin-azaarene conjugates with densely functionalized skeletons. DFT studies of the potential energy surface (B3LYP/6–31+G(d)+CPCM (dichloromethane)) of the reaction correlate the activity of different catalysts and support an intramolecular hydrogen-bond-assisted activation of the squaramide moiety in the transition state of the catalytic reaction.

SUBSTITUTED PYRIDIN-2-YLAMINE ANALOGUES

Substituted pyridin-2-ylamine analogues are provided, of the formula: wherein variables are as described herein. Such compounds are ligands that may be used to modulate specific receptor activity in vivo or in vitro, and are particularly useful in the tre

Synthesis, rotamer orientation, and calcium channel modulation activities of alkyl and 2-phenethyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(3- or 6-substituted-2-pyridyl)-5-pyridinecarboxylates

A group of racemic alkyl and 2-phenethyl 1,4-dihydro-2,6-dimethyl-3- nitro-4-(3- or 6-substituted-2-pyridyl)-5-pyridinecarboxylates (13a-q) was prepared using a modified Hantzsch reaction that involved the condensation of a 3- or 6-substituted-2-pyridinecarboxaldehyde (7a-j) with an alkyl or 2- phenethyl 3-aminocrotonate (11a-d) and nitroacetone (12). Nuclear Overhauser (NOE) studies indicated there is a significant rotamer fraction in solution where the pyridyl nitrogen is oriented above the 1,4-dihydropyridine ring, irrespective of whether a substituent is located at the 3- or 6-position. A potential H-bonding interaction between the pyridyl nitrogen free electron pair and the suitably positioned 1,4-dihydropyridine NH moiety may stablize this rotamer orientation. In vitro calcium channel antagonist and agonist activities were determined using guinea pig ileum longitudinal smooth muscle (GPILSM) and guinea pig left atrium (GPLA) assays, respectively. Compounds having an i-Pr ester substituent acted as dual cardioselective calcium channel agonists (GPLA)/smooth muscle-selective calcium channel antagonists (GPILSM), except for the C-4 3-nitro-2-pyridyl compound which exhibited an antagonist effect on both GPLA and GPILSM. In contrast, the compounds with a phenethyl ester group, which exhibited antagonist activity (IC50 = 10-5- 10-7 M range) on GPILSM, were devoid of cardiac agonist activity on GPLA. Structure-activity relationships showing the effect of a substituent (Me, CF3, C1, NO2, Ph) at the 3- or 6-position of a C-4 2-pyridyl moiety and a variety of ester substituents (Me, Et, i-Pr, PhCH2CH2-) upon calcium channel modulation are described. Compounds possessing a 3- or 6-substituted- 2-pyridyl moiety, in conjuction with an i-Pr ester substituent, are novel 1,4-dihydropyridine calcium channel modulators that offer a new drug design approach directed to the treatment of congestive heart failure and may also be useful as probes to study the structure-function relationships of calcium channels.