36225-16-8

Basic information

• Product Name: 6-bromo-4-hydroxy-3-methoxy-2-nitrobenzaldehyde
• CAS NO: 36225-16-8
• Molecular Formula: C₈H₆BrNO₅
• Molecular Weight: 276.0409
• Mol File: 36225-16-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 410.9°C at 760 mmHg
• Flash Point: 202.3°C
• Density: 1.821g/cm³
• Vapor Pressure: 2.44E-07mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: 6-bromo-4-hydroxy-3-methoxy-2-nitrobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-4-hydroxy-3-methoxy-2-nitrobenzaldehyde(36225-16-8)
• EPA Substance Registry System: 6-bromo-4-hydroxy-3-methoxy-2-nitrobenzaldehyde(36225-16-8)

Safety Data

• Hazardous Substances Data: 36225-16-8(Hazardous Substances Data)

Upstream product

• 52783-83-2 4-acetoxy-2-bromo-5-methoxybenzaldehyde 
• 881-68-5 vanillin acetate 
• 121-33-5 vanillin 
• 90766-55-5 4-acetoxy-6-bromo-3-methoxy-2-nitrobenzaldehyde 

Downstream Products

• 69905-17-5 3,7,8-trimethoxy-2-methyl-5-(5'-phenyl-1'-pentyl)quinoline-4(1H)-one 
• 109306-07-2 6-(2,2-dimethoxyethyl)-3,4-dimethoxy-2-nitrobenzamide 
• 109306-02-7 6-(2,2-dimethoxyethyl)-3,4-dimethoxy-2-nitrobenzonitrile 
• 109306-01-6 3,4-dimethoxy-2-nitro-6-(trimethylsilylethynyl)benzonitrile 
• 109305-99-9 6-bromo-3,4-dimethoxy-2-nitrobenzonitrile 
• 109305-96-6 6-bromo-3,4-dimethoxy-2-nitrobenzaldehyde 

Relevant articles and documents

Convergent First Total Synthesis of Melovinone: A Densely Substituted 3-Methoxy-4-quinolone Isolated from Melochia tomentosa L

The first total synthesis of melovinone, a nonrutaceous 3-methoxy-4-quinolone alkaloid isolated from Melochia tomentosa L., is reported. The target was acquired in a convergent fashion through the Suzuki-Miyaura cross-coupling reaction between an ortho-nitrobenzoic acid acetonyl ester derivative prepared from vanillin and potassium 5-phenyl-1-pentyltrifluoroborate, obtained from β-phenethyl bromide. The coupling was followed by a chemoselective reduction of the nitro group and a microwave-Assisted and AcOH-promoted cyclization with rearrangement of the resulting acetonyl anthranilate. This afforded a pseudane intermediate, which was selectively methylated on the 3-OH. The synthetic pathway enabled to reach the objective in 11 steps and 18% overall yield. The 1 H NMR spectra of the synthetic and natural product were in full agreement.