37669-64-0

Basic information

• Product Name: (5-BROMO-PYRIDIN-3-YL)-METHANOL
• Synonyms: (5-BROMO-PYRIDIN-3-YL)-METHANOL;3-BROMO-5-HYDROXYMETHYLPYRIDINE;AURORA KA-3029;(3-Bromo-pyridin-5-yl)methanol;(5-BROMO-3-PYRIDINYL)METHANOL;5-Bromo-3-pyridinemethanol;3-Bromopyridine-5-methanol;3-Bromo-5-pyridinemethanol
• CAS NO: 37669-64-0
• Molecular Formula: C₆H₆BrNO
• Molecular Weight: 188.02
• Product Categories: Building Blocks;Pyridine;Pyridines;NULL
• Mol File: 37669-64-0.mol
• Article Data: 85

Chemical Properties

• Boiling Point: 291.5 °C at 760 mmHg
• Flash Point: 130.1 °C
• Appearance: Clear pale yellow/Liquid or Low Melting Solid
• Density: 1.668 g/cm³
• Vapor Pressure: 0.00089mmHg at 25°C
• Refractive Index: 1.5940-1.5980
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 13.29±0.10(Predicted)
• CAS DataBase Reference: (5-BROMO-PYRIDIN-3-YL)-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (5-BROMO-PYRIDIN-3-YL)-METHANOL(37669-64-0)
• EPA Substance Registry System: (5-BROMO-PYRIDIN-3-YL)-METHANOL(37669-64-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 37669-64-0(Hazardous Substances Data)

Usage

General Description

"(5-Bromo-pyridin-3-yl)-methanol" is a chemical compound with the molecular formula C6H6BrNO. It is an organic compound with a pyridine ring that is substituted with a bromine atom and a hydroxymethyl group. (5-BROMO-PYRIDIN-3-YL)-METHANOL is commonly used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds. It can also act as a reagent in organic synthesis and as a precursor for the preparation of functionalized heterocycles. The presence of the bromine atom and the hydroxymethyl group make this compound useful in a wide range of chemical reactions and applications.

InChI:InChI=1/C6H6BrNO/c7-6-1-5(4-9)2-8-3-6/h1-3,9H,4H2

Upstream product

• 29681-44-5 5-bromo-3-pyridine carboxylic acid methyl ester 
• 39620-02-5 5-bromonicotinoyl chloride 
• 908864-98-2 1-(5-bromopyridin-3-yl)-N,N-dimethylmethanamine 
• 27828-71-3 5-hydroxynicotinic acid 
• 113118-81-3 5-bromopyridine-3-carbaldehyde 
• 20826-04-4 5-bromo-3-pyridinecarboxylic acid 
• 22620-36-6 3-bromo-5-(hydroxymethyl)pyridine hydrochloride 
• 20986-40-7 ethyl 5-bromo-3-pyridinecarboxylate 
• 20260-53-1 pyridine-3-carbonyl chloride hydrochloride 

Downstream Products

• 1035234-78-6 3-bromo-5-{[(4-methoxybenzyl)oxy]methyl}pyridine 
• 6221-06-3 methyl 5-formylpyridine-3-carboxylate 
• 1346687-20-4 (5-(furan-3-yl)pyridin-3-yl)methanol 
• 135124-70-8 (5-bromo-3-pyridinyl)methylamine 
• 120277-69-2 5-bromo-pyridin-3-ylmethyl chloride 
• 222551-22-6 3-(p-fluorophenyl)-5-hydroxymethyl-pyridine 
• 108337-85-5 2,6-dimethyl-4-(5-bromo-3-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-β-(N-benzyl-N-methylamino)ethyl ester 5-methyl ester 
• 166094-31-1 3-(N,N-dimethylthiocarbamoyl)-5-(2-tert-butyldiphenylsilyloxyethoxymethyl)pyridine 
• 166094-28-6 3-(N,N-dimethylcarbamoyl)-5-(2-tert-butyldiphenylsilyloxyethoxymethyl)pyridine 
• 166094-30-0 3-(N-methylthiocarbamoyl)-5-(2-tert-butyldiphenylsilyloxyethoxymethyl)pyridine 
• 166094-22-0 5-(2-tert-butyldiphenylsilyloxyethoxymethyl)-3-methoxycarbonylpyridine 
• 166094-27-5 3-(N-methylcarbamoyl)-5-(2-tert-butyldiphenylsilyloxyethoxymethyl)pyridine 
• 166094-29-7 3-thiocarbamoyl-5-(2-tert-butyldiphenylsilyloxyethoxymethyl)pyridine 
• 166094-26-4 3-carbamoyl-5-(2-tert-butyldiphenylsilyloxyethoxymethyl)pyridine 

Relevant articles and documents

Potent and Selective Human Neuronal Nitric Oxide Synthase Inhibition by Optimization of the 2-Aminopyridine-Based Scaffold with a Pyridine Linker

Neuronal nitric oxide synthase (nNOS) is an important therapeutic target for the treatment of various neurodegenerative disorders. A major challenge in the design of nNOS inhibitors focuses on potency in humans and selectivity over other NOS isoforms. Here we report potent and selective human nNOS inhibitors based on the 2-aminopyridine scaffold with a central pyridine linker. Compound 14j, the most promising inhibitor in this study, exhibits excellent potency for rat nNOS (Ki = 16 nM) with 828-fold n/e and 118-fold n/i selectivity with a Ki value of 13 nM against human nNOS with 1761-fold human n/e selectivity. Compound 14j also displayed good metabolic stability in human liver microsomes, low plasma protein binding, and minimal binding to cytochromes P450 (CYPs), although it had little to no Caco-2 permeability.

A Modular Synthesis of Teraryl-Based α-Helix Mimetics, Part 5: A Complete Set of Pyridine Boronic Acid Pinacol Esters Featuring Side Chains of Proteinogenic Amino Acids

Teraryl-based α-helix mimetics have proven to be useful compounds for the inhibition of protein-protein interactions (PPI). We have developed a modular and flexible approach for the synthesis of teraryl-based α-helix mimetics using pyridine containing boronic acid building blocks to increase the water solubility. Following our initial publication in which we have introduced the methodology in combination with sequential Pd-catalyzed cross-coupling for teraryl assembly, we can now report a complete set of pyridine based boronic acid building blocks decorated with side chains of all proteinogenic amino acids relevant for PPI (Ala, Arg, Asn, Asp, Cys, Gln, Glu, His, Ile, Leu, Lys, Met, Phe, Ser, Thr, Trp, Tyr, Val) to complement the core fragment set. For a representative set of teraryls we have studied the influence of the pyridine rings on the solubility of the assembled oligoarenes.

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.