30489-43-1

Basic information

• Product Name: IMIDAZO[1,2-A]PYRIDIN-3-YLMETHANOL
• Synonyms: 3-(HYDROXYMETHYL)IMIDAZO[1,2-A]PYRIDINE;IMIDAZO[1,2-A]PYRIDIN-3-YLMETHANOL;imidazo[1,2-a]pyridin-3-ylmethanol(SALTDATA: FREE);IiMidazo[1,2-a]pyridin-3-ylMethanol;Imidazo[1,2-a]pyridine-3-methanol;IMidazo[1,2-a]pyridine-3-ylMethanol
• CAS NO: 30489-43-1
• Molecular Formula: C8H8N2O
• Molecular Weight: 148.17
• Mol File: 30489-43-1.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Density: 1.26
• Refractive Index: 1.64
• Storage Temp.: 2-8°C
• PKA: 14.08±0.10(Predicted)
• CAS DataBase Reference: IMIDAZO[1,2-A]PYRIDIN-3-YLMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: IMIDAZO[1,2-A]PYRIDIN-3-YLMETHANOL(30489-43-1)
• EPA Substance Registry System: IMIDAZO[1,2-A]PYRIDIN-3-YLMETHANOL(30489-43-1)

Safety Data

• Hazardous Substances Data: 30489-43-1(Hazardous Substances Data)

Usage

General Description

Imidazo[1,2-a]pyridin-3-ylmethanol is a novel compound belonging to a broader class of chemical compounds known as Imidazopyridines. Discovered through organic chemistry processes, it features a unique structure that consists of methanol and imidazopyridine moieties. Often used in complex chemical reactions, it serves as a pharmaceutical intermediate, useful in the production of various types of drugs. However, little is known about its toxicity or potential side effects, so it's primarily used in research and development applications rather than in consumer products.

InChI:InChI=1/C8H8N2O/c11-6-7-5-9-8-3-1-2-4-10(7)8/h1-5,11H,6H2

Upstream product

• 274-76-0 imidazo[1,2-a]pyridine 
• 107-21-1 ethylene glycol 
• 504-29-0 2-aminopyridine 
• 1284210-49-6 tert-butyl prop-2-yn-1-yl(pyridin-2-yl)carbamate 
• 5857-45-4 3-methylimidazo[1,2-α]pyridine 
• 117459-95-7 N-(prop-2-yn-1-yl)pyridin-2-amine 
• 38427-94-0 N-(tert-butoxycarbonyl)-2-aminopyridine 
• 6188-43-8 imidazo[1,2-a]pyridine-3-carbaldehyde 
• 50-00-0 formaldehyd 

Downstream Products

• 113855-44-0 3-chloromethylimidazo[1,2-a]pyridine 

Relevant articles and documents

KIO4-mediated Selective Hydroxymethylation/Methylenation of Imidazo-Heteroarenes: A Greener Approach

Herein, we report a KIO4-mediated, sustainable and chemoselective approach for the one-pot C(sp2)?H bond hydroxymethylation or methylenation of imidazo-heteroarenes with formaldehyde, generated in situ via the oxidative cleavage of ethylene glycol or glycerol (renewable reagents) through the Malaprade reaction. In the presence of ethylene glycol, a series of 3-hydroxymethyl-imidazo-heteroarenes was obtained in good to excellent yields. These compounds are important intermediates to access pharmaceutical drugs, e.g., Zolpidem. Furthermore, by using glycerol, bis(imidazo[1,2-a]pyridin-3-yl)methane derivatives were selectively obtained in good to excellent yields.

Silver-catalyzed cyclization of N-(prop-2-yn-1-yl)pyridin-2-amines

We report herein the silver-catalyzed cycloisomerization of readily available N-(prop-2-yn-1-yl)pyridine-2-amines as a new and practical method for the synthesis of differently substituted 3-methylimidazo[1,2-a]pyridines. The isomerization reactions proce

Synthesis, stereochemistry and SAR of a series of minodronate analogues as RGGT inhibitors

Phosphonocarboxylate (PC) analogues of bisphosphonates are of interest due to their selective inhibition of a key enzyme in the mevalonate pathway, Rab geranylgeranyl transferase (RGGT). The dextrarotatory enantiomer of 2-hydroxy-3-(imidazo[1,2-a]pyridin-3-yl)-2-phosphonopropanoic acid (3-IPEHPC, 1) is the most potent PC-type RGGT inhibitor thus far identified. The absolute configuration of (+)-1 in the active site complex has remained unknown due to difficulties in obtaining RGGT inhibitor complex crystals suitable for X-ray diffraction analysis. However, we have now succeeded in crystallizing (-)-1 and here report its absolute configuration (AC) obtained by X-ray crystallography, thus also defining the AC of (+)-1. An Autodock Vina 1.1 computer modeling study of (+)-1 in the active site of modified RGGT binding GGPP (3DSV) identifies stereochemistry-dependent interactions that could account for the potency of (+)-1 and supports the hypothesis that this type of inhibitor binds at the TAG tunnel, inhibiting the second geranylgeranylation step. We also report a convenient 31P NMR method to determine enantiomeric excess of 1 and its pyridyl analogue 2, using α- and β-cyclodextrins as chiral solvating agents, and describe the synthesis of a small series of 1 α-X (X = H, F, Cl, Br; 7a-d) analogues to assess the contribution of the α-OH group to activity at enzyme and cellular levels. The IC50 of 1 was 5-10× lower than 7a-d, and the LED for inhibition of Rab11 prenylation in vitro was 2-8× lower than for 7a-d. However, in a viability reduction assay with J774 cells, 1 and 7b had similar IC50 values, ～10× lower than those of 7a and 7c-d.