109517-99-9

Basic information

• Product Name: 1,3-Benzenedicarboxaldehyde, 5-broMo-2-hydroxy-
• Synonyms: 1,3-Benzenedicarboxaldehyde, 5-broMo-2-hydroxy-;5-Bromo-2-hydroxy-1,3-benzenedicarboxaldehyde;5-bromo-2-hydroxyisophthalaldehyde
• CAS NO: 109517-99-9
• Molecular Formula: C₈H₅BrO₃
• Molecular Weight: 229.0275
• Mol File: 109517-99-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Benzenedicarboxaldehyde, 5-broMo-2-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzenedicarboxaldehyde, 5-broMo-2-hydroxy-(109517-99-9)
• EPA Substance Registry System: 1,3-Benzenedicarboxaldehyde, 5-broMo-2-hydroxy-(109517-99-9)

Safety Data

• Hazardous Substances Data: 109517-99-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1,3-Benzenedicarboxaldehyde, 5-bromo-2-hydroxyis used as a key monomer component in the development of recognition-encoded oligomers. Its unique structure allows for the creation of novel materials with specific recognition properties, making it valuable in fields such as biotechnology and materials science.
Used in Metal Organic Frameworks (MOF) Chemistry:
In the field of MOF chemistry, 1,3-Benzenedicarboxaldehyde, 5-bromo-2-hydroxyserves as an essential component. Its structural features enable the formation of complex and highly porous frameworks with potential applications in gas storage, catalysis, and drug delivery.
Used in Organic Cage Structures:
1,3-Benzenedicarboxaldehyde, 5-bromo-2-hydroxyis also utilized as a useful intermediate in the synthesis of organic cage structures. These cage-like molecules have potential applications in various industries, including pharmaceuticals, materials science, and energy storage, due to their unique properties and ability to encapsulate other molecules.

Upstream product

• 106-41-2 4-bromo-phenol 
• 100-97-0 hexamethylenetetramine 
• 50-00-0 formaldehyd 
• 76-05-1 trifluoroacetic acid 
• 111171-19-8 5-Bromo-2-hydroxy-3-hydroxymethyl-benzaldehyde 
• 6296-63-5 4-bromo-2,6-bis(hydroxymethyl)phenol 

Downstream Products

• 199010-29-2 4-bromo-2,6-bis[(2-pyridylmethyl)aminomethyl]phenol 
• 199010-31-6 4-bromo-2,6-bis[[2-(1-methyl-2-imidazolyl)ethyl]aminomethyl]phenol 
• 1094597-78-0 C₂₂H₁₅BrN₁₀OS₂ 

Relevant articles and documents

Two-component assembly of recognition-encoded oligomers that form stable H-bonded duplexes

A new family of recognition-encoded oligomers that form stable duplexes in chloroform have been prepared. Monomer building blocks composed of dialdehydes functionalised with either a trifluoromethylphenol or phosphine oxide H-bond recognition unit were prepared. The dialdehydes were coupled with diamines by imine formation and then reduction to give homo-oligomers between one and three recognition units in length. Duplex formation was characterised by 19F and 1H NMR titration experiments in toluene and in chloroform. For duplexes formed between length complementary H-bond donor and acceptor homo-oligomers, an order of magnitude increase in stability was observed for every base-pair added to the duplex in chloroform. The effective molarity for the intramolecular H-bonds responsible for zipping up the duplex is 30 mM, which results in the fully assembled duplex in all cases. The uniform increase in duplex stability with oligomer length suggests that the backbone structure and geometry is likely to be compatible with the formation of extended duplexes in longer oligomers.

Antioxidant, DNA interaction, molecular docking and cytotoxicity studies of aminoethylpiperazine-containing macrocyclic binuclear copper(II) complexes

A series of new macrocyclic binuclear copper(II) complexes of the type [Cu2L1–5(ClO4)](ClO4) (1–5) were synthesized by template condensation between precursor compounds 2,6-bis(4-aminoethylpiperazin-1-ylmethyl)-

Bimetallic Bis-anion Cascade Complexes of Magnesium in Nonaqueous Solution

Bimetallic magnesium(II) complexes are gaining significant interest in catalysis, yet their fundamental formation and behavior in organic media remain surprisingly unexplored relative to other divalent cations. To understand key principles of their formation, we investigate symmetric ditopic ligands bearing a phenolic backbone and characterize their ability to form dinuclear magnesium(II) cascade complexes with two bridging anions. High-fidelity production of bimetallic magnesium complexes relative to the monometallic complexes is indicative of positive cooperativity. Binding and recognition of analytes or substrates is a key characteristic of metal cascade complexes and relies on anion exchange, but this is also rarely studied with bimetallic magnesium complexes. Investigations with acetate, phosphate, and pyrophosphate reveal exchange of bridging nitrates using the bis-dipicolylamine complex. Rare seven-coordinate magnesium centers are found for the ester complex. The findings in this study provide formative steps to establish design principles for future generations of bimetallic magnesium(II) complexes.

Readily prepared inclusion forming chiral calixsalens

Calixsalens, chiral triangular hexaimines are readily synthesized by [3 + 3] cyclocondensation of trans-(R,R)-1,2-diaminocyclohexane with 2-hydroxyisophthalaldehyde derivatives. The usually rigid calixsalen ring is able to invert its conformation as a consequence of steric repulsion between bulky substituents at the C5 positions of the aromatic rings. The steric and electronic nature of the substituents does not affect only the conformation of the macrocycle. Small polar substituents enforce dimeric self-association to form an apohost where each of the monomers simultaneously serves as the host and the guest of its partner. Non-associating calixsalens form assemblies in which two symmetry-related molecules are arranged in a head-to-head fashion to form a capsule, or unimolecular cages that are able to entrap solvent molecules in their intrinsic voids.

One-pot Synthesis of a Truncated Cone-shaped Porphyrin Macrocycle and Its Self-assembly into Permanent Porous Material

Here, we report the synthesis of a truncated cone-shaped triangular porphyrinic macrocycle, P3L3, via a single step imine condensation of a cis-diaminophenylporphyrin and a bent dialdehyde-based linker as building units. X-ray diffra

Selective mono- and bis-oxidation of 2,6-bis(hydroxy methyl) phenols with active manganese dioxide

Selective mono- and bis-oxidations of 2, 6-bis (hydroxy methyl) phenols with active M(n)O2 were realized, giving 2-hydroxy-3- hydroxymethyl benzaldehydes and 2-hydroxyisophthalaldehydes in good yields. The influence of oxidant activity, reaction solvent and temperature on the selectivity were investigated, and favorable conditions developed.

A simple but highly efficient multi-formyl phenol-amine system for fluorescence detection of peroxide explosive vapour

A simple, highly stable, sensitive and selective fluorescent system for peroxide explosives was developed via an aromatic aldehyde oxidation reaction. The high efficiency arises from its higher HOMO level and multiple H-bonding. The sensitivity is obtaine

Mono- and diformylation of 4-substituted phenols: A new application of the duff reaction

Careful control of the reaction conditions in a modified Duff reaction using anhydrous trifluoroacetic acid as the solvent enables the selective synthesis of either 4-substituted 2-formylphenols (5-substituted salicylaldehydes) or 4-substituted 2,6-diformylphenols in one step starting from commercially available 4-substituted phenols in moderate to good yield.

Carboxylic Acid Functionalized Clathrochelate Complexes: Large, Robust, and Easy-to-Access Metalloligands

Polycarboxylate ligands are among the most important building blocks for the synthesis of metal-organic frameworks (MOFs). The ability to access these ligands in an efficient way is of key importance for future applications of MOFs. Here, we demonstrate that mono- and dinuclear clathrochelate complexes are versatile scaffolds for the preparation of polytopic carboxylate ligands. The largely inert clathrochelate complexes have a trigonal-bipyramidal shape. The synthesis of functionalized clathrochelates with two, three, four, or five carboxylic acid groups in the ligand periphery can be achieved in a few steps from simple starting materials. Apart from being easily accessible, the metalloligands display interesting characteristics for applications in metallasupramolecular chemistry and materials science: they are rigid, large (up to 2.2 nm), and robust and they can show additional functions (e.g., fluorescence or extra charge) depending on the metal ion that is present in the clathrochelate core. The utility of these new metalloligands in MOF chemistry is demonstrated by the synthesis of zinc- and zirconium-based coordination polymers. The combination of Zn(NO3)2 with clathrochelates having two or three carboxylic acid groups gives MOFs in which the clathrochelate ligands are connected by Zn4O clusters or zinc paddlewheel links. The structures of the resulting two- and three-dimensional networks could be established by single-crystal X-ray crystallography. The reaction of carboxylic acid functionalized clathrochelates with ZrCl4 gives amorphous powders that display permanent porosity after solvent removal.

Racemic Porous Organic Cage Crystal with Selective Gas Adsorption Behaviors

A mixture containing the reactions solution between 3,3′′,5,5′′-tetraformyl-4,4′′-[1,1′:4′,1′′-terphenyl]diol (TTD) and two enantiomers of cyclohexanediamine, respectively, affords porous racemic molecular crystal (1). Two kinds of homochiral [3+6] porous organic cage molecules 1 have been clearly disclosed by single crystal X-ray diffraction analysis, forming one-dimensional porous supramolecular channels with the narrowest size of 3.5 ?. The intercrossing channels of 1 enable the permanent porosity as well as the selective gas adsorption of acetylene and carbon dioxide over methane.