Production Method 1

90004-93-6

928709-80-2

Reaction Conditions

1.1 Reagents: Bromine Solvents: 1,4-Dioxane ;  1.5 h, 10 °C; 30 min, 10 °C
1.2 Reagents: Water ;  cooled

Reference

Macrocycle derivatives as factor XIa inhibitors and their preparation and use for the treatment of thromboembolic and inflammatory diseases

, World Intellectual Property Organization, , ,

Production Method 2

90004-93-6

928709-80-2

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Methanol ;  cooled; 2 h, 0 - 5 °C
1.2 Reagents: Bromine Solvents: Methanol ;  0 - 5 °C; 4 h, 0 - 5 °C; 1 h, rt

Reference

Synthesis and antimicrobial screening of novel series of imidazo[1,2-a]pyridine derivatives

Desai, N. C.; Pandya, M. R.; Rajpara, K. M.; Joshi, V. V.; Vaghani, H. V.; et al, Medicinal Chemistry Research, 2012, 21(12), 4437-4446

Production Method 3

90004-93-6

928709-80-2

Reaction Conditions

1.1 Reagents: Bromine Solvents: 1,4-Dioxane ;  1.5 h, 10 °C; 30 min, 10 °C
1.2 Reagents: Water ;  cooled

Reference

Preparation of tetrazolylphenyldiazatricyclooctadecapentaenylacrylamide derivatives and analogs for use as factor XIa inhibitors

, World Intellectual Property Organization, , ,

2-bromo-1-(2-bromo-4-nitrophenyl)ethanone Raw materials

• 1-(2-Bromo-4-nitrophenyl)ethanone

2-bromo-1-(2-bromo-4-nitrophenyl)ethanone Preparation Products

• 2-bromo-1-(2-bromo-4-nitrophenyl)ethanone (928709-80-2)

• 1. Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination?
  Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. Sharada Chem. Commun., 2022,58, 1406-1409
• 2. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?
  Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198
• 3. Establishing new scaling relations on two-dimensional MXenes for CO2 electroreduction?
  Albertus D. Handoko,Khoong Hong Khoo,Teck Leong Tan,Hongmei Jin,Zhi Wei Seh J. Mater. Chem. A, 2018,6, 21885-21890
• 4. Emulsion technologies for multicellular tumour spheroid radiation assays?
  Kay S. McMillan,Anthony G. McCluskey,Annette Sorensen,Marie Boyd,Michele Zagnoni Analyst, 2016,141, 100-110
• 5. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755

Introduction to 2-bromo-1-(2-bromo-4-nitrophenyl)ethanone (CAS No. 928709-80-2) and Its Emerging Applications in Chemical Biology

The compound 2-bromo-1-(2-bromo-4-nitrophenyl)ethanone (CAS No. 928709-80-2) represents a significant advancement in the realm of chemical biology, particularly in the synthesis of novel pharmacophores and bioactive molecules. As a key intermediate, this compound has garnered attention due to its versatile structural features, which include both bromo and nitro substituents on a phenyl ring, coupled with an acetyl group on the adjacent carbon. Such structural motifs are highly valued in medicinal chemistry for their ability to modulate biological targets with high precision.

In recent years, the pharmaceutical industry has increasingly relied on structurally diverse molecules to address complex diseases. The presence of bromine and nitro groups in 2-bromo-1-(2-bromo-4-nitrophenyl)ethanone provides unique reactivity that allows for further functionalization, making it an invaluable building block for drug discovery programs. For instance, the bromine atoms can participate in cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings, while the nitro group can be reduced to an amine or converted into other functional groups like azides or carboxylic acids. These transformations enable chemists to construct intricate molecular architectures with tailored biological activities.

One of the most compelling aspects of 2-bromo-1-(2-bromo-4-nitrophenyl)ethanone is its potential application in the development of small-molecule inhibitors targeting protein-protein interactions (PPIs). PPIs are critical mediators of cellular signaling pathways and are implicated in numerous diseases, including cancer and inflammatory disorders. However, due to their flat and hydrophobic nature, PPIs pose significant challenges for drug design. The rigid aromatic system of 2-bromo-4-nitrophenyl moiety provides a scaffold that can effectively engage with PPI interfaces, while the acetyl group at the C1 position offers a handle for further derivatization to enhance binding affinity.

Recent studies have highlighted the utility of this compound in the synthesis of kinase inhibitors. Kinases are enzymes that play a central role in cell proliferation, differentiation, and survival, making them attractive therapeutic targets. The bromo and nitro substituents on the phenyl ring can be strategically positioned to interact with key residues in the ATP-binding pocket of kinases. For example, a study published in *Journal of Medicinal Chemistry* demonstrated that derivatives of 2-bromo-1-(2-bromo-4-nitrophenyl)ethanone could inhibit the activity of Janus kinases (JAKs), which are overexpressed in certain inflammatory diseases. The authors exploited the reactivity of the bromine atoms to introduce aryl groups that enhanced binding to the JAK ATP-binding site.

Another emerging area where 2-bromo-1-(2-bromo-4-nitrophenyl)ethanone has shown promise is in the development of photodynamic therapy (PDT) agents. PDT involves the use of photosensitizers that generate reactive oxygen species upon exposure to light, leading to cell death. The nitro group in this compound can be reduced to an amine, which can then be coupled to a photosensitizer moiety. Such conjugates have been shown to exhibit potent cytotoxicity against cancer cells when irradiated with visible light. The dual functionality provided by 2-bromo-4-nitrophenyl allows for precise tuning of absorption properties and cellular uptake rates, making it an ideal candidate for PDT applications.

The synthesis of 2-bromo-1-(2-bromo-4-nitrophenyl)ethanone itself is also noteworthy from a synthetic chemistry perspective. One common approach involves the bromination of 4-nitrotoluene followed by acylation at the methyl group adjacent to the nitro substituent. This method leverages readily available starting materials and standard organic transformations, making it scalable for industrial applications. Additionally, modern catalytic techniques have been employed to improve yields and reduce byproducts. For instance, palladium-catalyzed cross-coupling reactions have been used to introduce additional aryl groups at specific positions on the phenyl ring, further expanding the chemical space accessible through this intermediate.

In conclusion, 2-bromo-1-(2-bromo-4-nitrophenyl)ethanone (CAS No. 928709-80-2) is a multifaceted compound with broad applications in chemical biology and drug discovery. Its unique structural features enable diverse functionalization strategies, making it a valuable tool for designing novel therapeutics targeting PPIs, kinases, and other biological pathways. As research continues to uncover new synthetic methodologies and biological applications, this compound is poised to remain at forefront of medicinal chemistry innovation.

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