247174-18-1

Basic information

• Product Name: 6-BROMO-2-METHOXYNAPHTHALENE-1-CARBALDEHYDE
• Synonyms: 6-BROMO-2-METHOXYNAPHTHALENE-1-CARBALDEHYDE;6-BroMo-2-Methoxy-1-naphthaldehyde
• CAS NO: 247174-18-1
• Molecular Formula: C₁₂H₉BrO₂
• Molecular Weight: 265.1
• Mol File: 247174-18-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 110 °C
• Boiling Point: 234-240 °C(Press: 15 Torr)
• Appearance: /
• Density: 1.511±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-BROMO-2-METHOXYNAPHTHALENE-1-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-2-METHOXYNAPHTHALENE-1-CARBALDEHYDE(247174-18-1)
• EPA Substance Registry System: 6-BROMO-2-METHOXYNAPHTHALENE-1-CARBALDEHYDE(247174-18-1)

Safety Data

• Hazardous Substances Data: 247174-18-1(Hazardous Substances Data)

Upstream product

• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 53815-56-8 6-Bromo-2-hydroxy-1-naphthaldehyde 
• 74-88-4 methyl iodide 
• 4885-02-3 Dichloromethyl methyl ether 
• 68-12-2 N,N-dimethyl-formamide 
• 93-61-8 N-methyl-N-phenylformamide 

Downstream Products

• 1007347-52-5 6-(4-fluorophenyl)-2-methoxy-1-naphthaldehyde 
• 92455-04-4 6-bromo-1-chloro-2-methoxynaphthalene 
• 66996-59-6 1,6-dibromo-2-methoxynaphthalene 

Relevant articles and documents

Mononuclear Zn(ii)- and Cu(ii)-complexes of a hydroxynaphthalene-derived dipicolylamine: Fluorescent sensing behaviours toward pyrophosphate ions

Mononuclear Zn(ii)-DPA and Cu(ii)-DPA complexes crafted on 2-hydroxy-6-cyanonaphthalene fluorophore selectively recognize PPi over ATP and other anions including inorganic phosphates in aqueous medium, showing turn-on type fluorescence enhancements. Coordination of a hydroxyl group of the fluorophore, directly or in alkoxy form, to the central metal ion is crucial for the sensing processes. Both the complexes elicit a fluorescence increase in a time-dependent fashion.

Discovery and Rational Design of Natural-Product-Derived 2-Phenyl-3,4-dihydro-2H-benzo[f]chromen-3-amine Analogs as Novel and Potent Dipeptidyl Peptidase 4 (DPP-4) Inhibitors for the Treatment of Type 2 Diabetes

Starting from the lead isodaphnetin, a natural product inhibitor of DPP-4 discovered through a target fishing docking based approach, a series of novel 2-phenyl-3,4-dihydro-2H-benzo[f]chromen-3-amine derivatives as potent DPP-4 inhibitors are rationally designed utilizing highly efficient 3D molecular similarity based scaffold hopping as well as electrostatic complementary methods. Those ingenious drug design strategies bring us approximate 7400-fold boost in potency. Compounds 22a and 24a are the most potent ones (IC50 ≈ 2.0 nM) with good pharmacokinetic profiles. Compound 22a demonstrated stable pharmacological effect. A 3 mg/kg oral dose provided >80% inhibition of DPP-4 activity within 24 h, which is comparable to the performance of the long-acting control omarigliptin. Moreover, the efficacy of 22a in improving the glucose tolerance is also comparable with omarigliptin. In this study, not only promising DPP-4 inhibitors as long acting antidiabetic that are clinically on demand are identified, but the target fish docking and medicinal chemistry strategies were successfully implemented.

Decarbonylative halogenation by a vanadium complex

Metal-catalyzed halogenation of the C-H bond and decarbonylation of aldehyde are conventionally done in nature. However, metal-mediated decarbonylative halogenation is unknown. We have developed the first metal-mediated decarbonylative halogenation reaction starting from the divanadium oxoperoxo complex K3V5+2(O 22-)4(O2-)2(μ-OH) (1). A concerted decarbonylative halogenation reaction was proposed based on experimental observations.