56479-63-1

Usage

Uses

Used in Pharmaceutical Industry:
3-bromo-4-dimethylamino-benzaldehyde is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs, particularly those targeting specific receptors or enzymes in the body.
Used in Chemical Synthesis:
In the field of organic chemistry, 3-bromo-4-dimethylamino-benzaldehyde serves as a valuable building block for the creation of more complex molecules. Its bromine and dimethylamino substituents can be further modified or used as starting points for the synthesis of a wide range of organic compounds, including dyes, pigments, and other specialty chemicals.
Used in Material Science:
3-bromo-4-dimethylamino-benzaldehyde's unique structure and properties make it a candidate for use in the development of new materials with specific characteristics. For example, it could be used in the design of novel polymers, coatings, or other materials with tailored properties for various applications, such as electronics, sensors, or energy storage devices.
Used in Research and Development:
3-bromo-4-dimethylamino-benzaldehyde is also utilized in academic and industrial research settings as a model compound for studying various chemical reactions and processes. Its reactivity and structural features make it an interesting subject for exploring new synthetic methods, understanding reaction mechanisms, and developing innovative applications in various fields.

InChI:InChI=1/C9H10BrNO/c1-11(2)9-4-3-7(6-12)5-8(9)10/h3-6H,1-2H3

Upstream product

• 100-10-7 4-dimethylamino-benzaldehyde 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 67-56-1 methanol 

Downstream Products

• 84562-58-3 N'-[1-(3-Bromo-4-dimethylamino-phenyl)-meth-(E)-ylidene]-2,6-dichloro-benzene-1,4-diamine 
• 1402432-05-6 (E)-2-[3-bromo-4-(dimethylamino)benzylidene]-5,6-dimethoxyindan-1-one 
• 1584546-66-6 (E)-3-(3-bromo-4-dimethylamino-benzylidene)-6-bromochroman-4-one 
• 28164-48-9 3-bromo-4-(methylamino)benzaldehyde 
• 500165-27-5 6-N,N'-dimethylamino-3-formyl-1-phenyl boronicacid 

Relevant academic research and scientific papers

Supramolecular organization of bis(3-halo-4-dimethylaminobenzylidene) hydrazines

Bis(3-bromo-4-dimethylaminobenzylidene)hydrazine and bis(3-chloro-4- dimethylaminobenzylidene)hydrazine have been synthesized, and their monoclinic crystal structures solved in space group P21/c. For the bromo derivative at 150 K, a = 10.4505(2

Toward bioluminescence in the near-infrared region: Tuning the emission wavelength of firefly luciferin analogues by allyl substitution

The synthesis and bioluminescence of allyl-substituted luciferin derivatives as substrates for firefly luciferase are reported. The allylation of luciferins induced bathochromic shift (15–40 nm) of the bioluminescence emission. Upon combination with other chemical modifications for bioluminescence wavelength tuning, novel red emitting luciferin analogues were obtained with emission maxima at 685 and 690 nm.

Ni-NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics

Herein, we report a facile method for the synthesis of Ni-NiO heterojunction nanoparticles, which we utilized for the nuclear halogenation reaction of phenol and substituted phenols usingN-bromosuccinimide (NBS). A remarkablepara-selectivity was achieved for the halogenated products under semi-aqueous conditions. Interestingly, blocking of thepara-position of phenol offeredortho-selective halogenation. In addition, the Ni-NiO nanoparticles catalyzed the oxidative esterification of carbonyl compounds with alcohol, diol or dithiol in the presence of a catalytic amount of NBS. It was observed that the aromatic carbonyls substituted with an electron-donating group favoured nuclear halogenation, whereas an electron-withdrawing group substitution in carbonyl compounds facilitated the oxidation reaction. In addition, the catalyst was magnetically separated and recycled 10 times. The tuned electronic structure at the Ni-NiO heterojunction controlled selectivity and activity as no suchpara-selectivity was observed with commercially available NiO or Ni nanoparticles.

Design and optimisation of a small-molecule TLR2/4 antagonist for anti-tumour therapy

In anti-tumour therapy, the toll-like receptor 2/4 (TLR2/4) signalling pathway has been a double-edged sword. TLR2/4 agonists are commonly considered adjuvants for immune stimulation, whereas TLR2/4 antagonists demonstrate more feasibility for anti-tumour therapy under specific chronic inflammatory situations. In individuals with cancer retaliatory proliferation and metastasis after surgery, blocking the TLR2/4 signalling pathway may produce favourable prognosis for patients. Therefore, here, we developed a small-molecule co-inhibitor that targets the TLR2/4 signalling pathway. After high-throughput screening of a compound library containing 14 400 small molecules, followed by hit-to-lead structural optimisation, we finally obtained the compound TX-33, which has effective inhibitory properties against the TLR2/4 signalling pathways. This compound was found to significantly inhibit multiple pro-inflammatory cytokines released by RAW264.7 cells. This was followed by TX-33 demonstrating promising efficacy in subsequent anti-tumour experiments. The current results provide a novel understanding of the role of TLR2/4 in cancer and a novel strategy for anti-tumour therapy.

Stepwise mechanism for the bromination of arenes by a hypervalent iodine reagent

A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring.

Alkylammoniotrifluoroborate functionalized polystyrenes: Polymeric pre-catalysts for the metal-free borylation of heteroarenes

Three polymeric versions of ansa-N,N-dialkylammoniumtrifluoroborate ambiphilic molecules based on the styrene motif (poly(1-NMe2H+-2-BF3--4-styrene) (P-Me), poly(1-NEt2H+-2-BF3--4-styrene) (P-Et) and poly(1-piperidinyl-H+-2-BF3--4-styrene) (P-Pip)) were synthesized, characterized and tested as heterogeneous pre-catalysts for the borylation of electron-rich heteroarenes. These heterogeneous versions of previously reported pre-catalysts show similar reactivity patterns and represent the first examples of solid-supported FLP metal-free catalysts for the C-H borylation of heteroarenes.

Environmentally benign indole-catalyzed position-selective halogenation of thioarenes and other aromatics

Halogenated aromatic compounds are the cores of many pharmaceutical, agricultural and chemical products but they are commonly prepared using electrophilic halogenation reactions in non-green chlorinated solvents under harsh conditions. A separate problem happens in the aromatic halogenation of thioarenes because they readily undergo oxidative side-reactions. Herein we report an environmentally benign electrophilic bromination of aromatics using an indole-catalytic protocol, which is suitable for a wide range of substrates including thioarenes.

The effects of bromine atoms on the photophysical and photochemical properties of 3-cinnamoylcoumarin derivatives

Eight coumarin derivatives (T1-T8) with or without modification using one or two bromine atoms were synthesized through the aldol condensation reaction. Their photophysical, photochemical and electrochemical properties were investigated. It was shown that

DMABI tripod structures with sensing capabilities: Synthesis, characterization and fluorescence analysis

We present herein the synthesis, and the structural and spectroscopic analysis of a non-planar tripod-shaped p-(N,N′-dimethylamino)benzyliden-1,3-indandione (DMABI) chromophore. This novel molecule is composed of a Si core with three incorporated arms, each of them contains a 1,3-indandione derivative with an electron donating (-NMe2) group, thus providing fluorescence capabilities. We prepared a DMABI arm by coupling a p-(N,N′-dimethylamino)benzaldehyde (DMAB) tripod substituted molecule with 1,3-indandione via aldol condensation. The structures of DMAB-tripods were confirmed by spectroscopic data and studied by quantum chemical calculations. Fluorescence spectroscopy was used for optical characterization. Quantum yields and the corresponding lifetimes reveal typical characteristics of conjugated derivatives. Finally, we monitored the enhancement in fluorescence intensity of compound 1 in the presence of 4-chloro-2,6-dinitroaniline (4CDNA) in the range between 0 and 20 mg L-1. We justify this enhancement by calculated energies and the distribution of the HOMO and the LUMO for DMABI-tripod and 4CDNA.

Aggregation-induced emission enhancement in halochalcones

A family of push-pull fluorophores, consisting of a chalcone core decorated with electron-donating substituents and halogen atoms, was designed and synthesized. Luminescence studies were performed in solution, aggregate form and in the solid state. Although some compounds are only weakly fluorescent in solution, all are emissive in the solid state showing aggregation-induced emission enhancement. In the crystalline state, the halogen atoms are not involved in halogen bonds but their presence strongly influences the aggregation-induced emission properties of the fluorophores.