53811-50-0

Basic information

• Product Name: 6-BROMO-2,3-DIMETHOXY-BENZALDEHYDE
• Synonyms: SALOR-INT L135259-1EA;6-BROMO-2,3-DIMETHOXY-BENZALDEHYDE
• CAS NO: 53811-50-0
• Molecular Formula: C₉H₉BrO₃
• Molecular Weight: 245.07
• Mol File: 53811-50-0.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-BROMO-2,3-DIMETHOXY-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-2,3-DIMETHOXY-BENZALDEHYDE(53811-50-0)
• EPA Substance Registry System: 6-BROMO-2,3-DIMETHOXY-BENZALDEHYDE(53811-50-0)

Safety Data

• Hazardous Substances Data: 53811-50-0(Hazardous Substances Data)

Upstream product

• 20035-41-0 6-bromo-2-hydroxy-3-methoxybenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 492-88-6 3-ethoxysalicylaldehyde 
• 74-88-4 methyl iodide 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 107290-27-7 (6-bromo-2,3-dimethoxyphenyl)methanol 
• 5653-67-8 2,3-dimethoxybenzyl alcohol 
• 1314031-88-3 2-bromo-5,6-dimethoxybenzaldehyde O-methyloxime 
• 584-08-7 potassium carbonate 
• 20035-45-4 6-bromo-3-ethoxy-2-hydroxybenzaldehyde 
• 7150-01-8 2-acetoxy-3-methoxybenzaldehyde 
• 83983-71-5 6-bromo-2,3-dihydroxybenzaldehyde 

Downstream Products

• 6900-99-8 norchelerythrine 
• 1491841-51-0 4-benzyl-7,8-dimethoxy-3-phenylisoquinoline 
• 128957-88-0 7-(6-Bromo-2,3-dimethoxy-benzyl)-5-methylsulfanyl-5,7,8,9-tetrahydro-1,3-dioxa-7-aza-cyclohepta[f]inden-6-one 
• 128957-89-1 7-(6-Bromo-2,3-dimethoxy-benzyl)-5,7,8,9-tetrahydro-1,3-dioxa-7-aza-cyclohepta[f]inden-6-one 
• 128957-90-4 7-(6-Bromo-2,3-dimethoxy-benzyl)-6,7-dihydro-5H-1,3-dioxa-7-aza-cyclohepta[f]indene 
• 128957-87-9 (2-Benzo[1,3]dioxol-5-yl-ethyl)-(6-bromo-2,3-dimethoxy-benzyl)-amine 
• 3723-02-2 3,4-dimethoxyhomophthalic acid 
• 107290-24-4 1-(6'-bromo-2',3'-dimethoxybenzyl)-4-hydroxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 
• 107290-24-4 1-(6'-bromo-2',3'-dimethoxybenzyl)-4-hydroxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 
• 107290-31-3 [1-Benzo[1,3]dioxol-5-yl-2-(6-bromo-2,3-dimethoxy-phenyl)-eth-(E)-ylidene]-(2,2-diethoxy-ethyl)-amine 
• 107290-32-4 N-<2-(6'-bromo-2',3'-dimethoxyphenyl)-1-(3,4-methylenedioxyphenyl)ethyl>aminoacetaldehyde diethyl acetal 
• 107290-22-2 1-(6'-bromo-2',3'-dimethoxybenzyl)-4-hydroxy-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes via a monodentate transient directing group strategy

A facile and efficient monodentate transient directing group strategy was developed to enable the palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes. A broad scope of benzaldehydes were transformed into the desired products by employing 2-amino-5-chlorobenzotrifluoride as a monodentate transient directing group, demonstrating good functional group tolerance. Mild reaction conditions and no requirement for a silver salt are also features of this strategy.

Modular, Metal-Catalyzed Cycloisomerization Approach to Angularly Fused Polycyclic Aromatic Hydrocarbons and Their Oxidized Derivatives

Palladium-catalyzed cross-coupling reactions of 2-bromobenzaldehyde and 6-bromo-2,3-dimethoxybenzaldehyde with 4-methyl-1-naphthaleneboronic acid and acenaphthene-5-boronic acid gave corresponding o-naphthyl benzaldehydes. Corey-Fuchs olefination followed by reaction with n-BuLi led to various 1-(2-ethynylphenyl)naphthalenes. Cycloisomerization of individual 1-(2-ethynylphenyl)naphthalenes to various benzo[c]phenanthrene (BcPh) analogues was accomplished smoothly with catalytic PtCl2 in PhMe. In the case of 4,5-dihydrobenzo[l]acephenanthrylene, oxidation with DDQ gave benzo[l]acephenanthrylene. The dimethoxy-substituted benzo[c]phenanthrenes were demethylated with BBr3 and oxidized to the o-quinones with PDC. Reduction of these quinones with NaBH4 in THF/EtOH in an oxygen atmosphere gave the respective dihydrodiols. Exposure of the dihydrodiols to N-bromoacetamide in THF-H2O led to bromohydrins that were cyclized with Amberlite IRA 400 HO- to yield the series 1 diol epoxides. Epoxidation of the dihydrodiols with mCPBA gave the isomeric series 2 diol epoxides. All of the hydrocarbons as well as the methoxy-substituted ones were crystallized and analyzed by X-ray crystallography, and these data are compared to other previously studied BcPh derivatives. The methodology described is highly modular and can be utilized for the synthesis of a wide variety of angularly fused polycyclic aromatic hydrocarbons and their putative metabolites and/or other derivatives.

Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization

A methyl ketone, an aryl bromide, an electrophile, and ammonium chloride were combined in a four-component, three-step, and one-pot coupling procedure to furnish substituted isoquinolines in overall yields of up to 80%. This protocol utilizes the palladiu