14142-90-6

Basic information

• Product Name: 5-(chloromethyl)-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine
• Synonyms: 5-(Chloromethyl)-2,2,8-trimethyl-4H-(1,3)dioxino(4,5-c)pyridine; 5-(Chloromethyl)-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine; 5-Chloromethyl-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine
• CAS NO: 14142-90-6
• Molecular Formula: C₁₁H₁₄ClNO₂
• Molecular Weight: 227.6874
• Mol File: 14142-90-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 316.2°C at 760 mmHg
• Flash Point: 145°C
• Density: 1.173g/cm³
• Vapor Pressure: 0.000773mmHg at 25°C
• Refractive Index: 1.52
• CAS DataBase Reference: 5-(chloromethyl)-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(chloromethyl)-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine(14142-90-6)
• EPA Substance Registry System: 5-(chloromethyl)-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine(14142-90-6)

Safety Data

• Hazardous Substances Data: 14142-90-6(Hazardous Substances Data)

Upstream product

• 13331-80-1 5-chloromethyl-4-hydroxymethyl-2-methyl-pyridin-3-ol; hydrochloride 
• 67-64-1 acetone 
• 1136-52-3 (2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol 
• 14309-02-5 4,5-bis-aminomethyl-2-methyl-pyridin-3-ol; trihydrochloride 
• 58-56-0 pyridoxal hydrochloride 

Downstream Products

• 352438-93-8 α⁴,3-O-isopropylidene-α⁵-deoxy-α⁵-[diethyl(1'-fluoro-1'-phenylsulfonyl)phosphonomethyl]pyridoxine 
• 26210-18-4 (4-formyl-3-hydroxy-2-methyl-5-pyridyl)methylphosphonic acid 
• 55273-17-1 5-benzoylsulfanylmethyl-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine 
• 1411702-70-9 5-[(triphenylphosphonio)methyl]-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine chloride 

Relevant articles and documents

A convenient method for chemoselective O-methylation of hydroxypyridines

ethereal-diazomethane in tert-butanol at -20 °C to rt, afforded the corresponding 3-methoxypyridine derivatives (2a-g) in 54-94% yield.

"Click" assembly of novel dual inhibitors of AChE and MAO-B from pyridoxine derivatives for the treatment of Alzheimer's disease

This study fast synthesizes numerous functionalized pyridoxines using click chemistry and assayed in vitro as inhibitors of the acetylcholinesterase (AChE), butyrylcholinesterase, and two monoamine oxidase (MAO) isoforms, MAO-A and MAO-B. Most of the obtained compounds demonstrate good AChE and selective MAO-B inhibitory activities in the micromolar range, especially one compound, called 4k5, exhibits excellent inhibitory performance against AChE (IC50 = 0.0816 ± 0.075 μM) and MAO-B (IC50 = 0.039 ± 0.003 μM). Finally, a docking study is carried out, demonstrating potential binding orientations and interactions of the compounds in terms of the AChE and MAO-B active sites.

Pyridoxine-resveratrol hybrids as novel inhibitors of MAO-B with antioxidant and neuroprotective activities for the treatment of Parkinson's disease

A series of pyridoxine-resveratrol hybrids were designed and synthesized as monoamine oxidase B inhibitors for the treatment of Parkinson's disease. Most of them exhibited potent inhibitory activities on MAO-B with high selectivity. Specifically, compounds 12a, 12g and 12l showed the most excellent inhibition to hMAO-B with the IC50 values of 0.01 μM, 0.01 μM and 0.02 μM, respectively. Further reversibility study demonstrated that 12a and 12l were reversible and 12g was irreversible MAO-B inhibitors. Molecular docking studies of MAO revealed the binding mode and high selectivity of these compounds with MAO-B. In addition, these three representative compounds also exhibited low cytotoxicity and excellent neuroprotective effect in the test on H2O2-induced PC-12 cell injury. Moreover, 12a, 12g and 12l showed good antioxidant activities and high blood-brain barrier permeability. Overall, all of these results highlighted 12a, 12g and 12l were potential and excellent MAO-B inhibitors for PD treatment.

A Convergent Triflate Displacement Approach to (α-Monofluoroalkyl)phosphonates

(Formula Presented) Treatment of primary alkyl triflates or iodides with the potassium salt of diethyl (α-fluoro-α-phenylsulfonylmethyl)phosphonate yields (α-fluoro-α-phenylsulfonylalkyl)phosphonates. These can be cleanly desulfonated, in a matter of minu