Production Method 1

552-89-6

20357-21-5

56990-05-7

20357-20-4

1559060-83-1

882772-99-8

5551-12-2

213382-42-4

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide ,  Sulfuric acid ;  3 h, rt
1.2 Reagents: Water ;  cooled

Reference

Reexamination of the Bromination of 2-Nitrobenzaldehyde with NBS or NaBr-NaIO4 in Sulfuric Acid

Cummings, Matthew M.; et al, Synthetic Communications, 2014, 44(7), 954-958

2-Bromo-6-nitrobenzaldehyde Raw materials

• 2-Nitrobenzaldehyde

2-Bromo-6-nitrobenzaldehyde Preparation Products

• 4,5-Dibromo-2-nitrobenzaldehyde (56990-05-7)
• 5-Bromo-2-nitrobenzaldehyde (20357-20-4)
• Benzaldehyde, 3,4-dibromo-2-nitro- (1559060-83-1)
• 3-Bromo-2-nitrobenzaldehyde (882772-99-8)
• 4-Bromo-2-nitrobenzaldehyde (5551-12-2)
• 2-Bromo-6-nitrobenzaldehyde (20357-21-5)
• Benzaldehyde, 3,6-dibromo-2-nitro- (213382-42-4)

• 1. Polyaza heterocycles. Part 3. Halogenation of 1-substituted quinoxalino[2,3-c]cinnolines: mechanistic implications
  Ian W. Harvey,David M. Smith,Charles R. White J. Chem. Soc. Perkin Trans. 1 1996 1699
• 2. Acid-catalysed cyclisation of o-sulphonamido ketene dithioacetal S-oxides: a novel synthesis of the indole ring system
  Alan T. Hewson,Kevin Hughes,Stewart K. Richardson,David A. Sharpe,Alan H. Wadsworth J. Chem. Soc. Perkin Trans. 1 1991 1565
• 3. Subnanometric Pt clusters supported on MgO-incorporated porous carbon as efficient metal–base bifunctional catalysts for reductive heterocyclization reactions
  Yaping Song,Ruifang Xue,Li Wang,Nan Li,Zhijun Fang,Yanghe Fu,De-Li Chen,Weidong Zhu,Fumin Zhang Green Chem. 2023 25 1107
• 4. Organic chemistry
  J. Chem. Soc. Abstr. 1919 116 i145

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Nitrobenzenes Nitrobenzaldehydes

Chemical Profile of 2-Bromo-6-nitrobenzaldehyde (CAS No. 20357-21-5)

2-Bromo-6-nitrobenzaldehyde, identified by the Chemical Abstracts Service Number (CAS No.) 20357-21-5, is a significant organic compound widely utilized in the field of pharmaceutical synthesis and chemical research. This aromatic aldehyde derivative features both bromine and nitro substituents, which endow it with unique reactivity and make it a valuable intermediate in the development of various chemical entities.

The structural configuration of 2-Bromo-6-nitrobenzaldehyde consists of a benzene ring substituted at the 2-position with a bromine atom and at the 6-position with a nitro group, with an aldehyde functional group at the 1-position. This specific arrangement imparts distinct electronic properties, influencing its interactions with other molecules during synthetic transformations. The presence of both electron-withdrawing nitro and bromo groups enhances its utility as a building block in organic synthesis, particularly in constructing more complex heterocyclic compounds.

In recent years, 2-Bromo-6-nitrobenzaldehyde has garnered attention in the pharmaceutical industry due to its role as a precursor in the synthesis of biologically active molecules. Its reactivity allows for facile functionalization at multiple positions, enabling chemists to explore diverse chemical space. For instance, the aldehyde group can undergo condensation reactions to form Schiff bases, which are known for their pharmacological properties. Additionally, the bromo and nitro groups can be selectively modified through various coupling or reduction reactions, facilitating the construction of more intricate molecular architectures.

One of the most compelling applications of 2-Bromo-6-nitrobenzaldehyde lies in its use as an intermediate in the development of novel therapeutic agents. Researchers have leveraged its structural features to design compounds with potential antimicrobial, anti-inflammatory, and anticancer activities. The nitro group, in particular, has been shown to enhance binding affinity to biological targets, making it a strategic element in drug design. Recent studies have highlighted its incorporation into quinone-based compounds, which exhibit promising cytotoxic effects against certain cancer cell lines.

The compound’s utility extends beyond pharmaceuticals into agrochemicals and material science. In agrochemical research, derivatives of 2-Bromo-6-nitrobenzaldehyde have been investigated for their herbicidal and fungicidal properties. The ability to introduce additional functional groups allows for fine-tuning of biological activity, making it a versatile scaffold for designing environmentally friendly crop protection agents. Furthermore, its incorporation into polymer precursors has shown potential in developing advanced materials with tailored electronic and optical properties.

From a synthetic chemistry perspective, 2-Bromo-6-nitrobenzaldehyde serves as a cornerstone for exploring new reaction pathways and methodologies. Its compatibility with transition metal catalysis has enabled innovative cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, which are pivotal in constructing carbon-carbon bonds efficiently. These advancements have not only streamlined synthetic routes but also opened doors to accessing previously inaccessible molecular scaffolds.

The safety and handling of 2-Bromo-6-nitrobenzaldehyde are critical considerations in industrial and laboratory settings. While it is not classified as a hazardous substance under standard regulations, appropriate precautions must be taken to prevent exposure due to its potential irritant properties. Standard laboratory practices, including the use of personal protective equipment (PPE) such as gloves and safety goggles, along with adequate ventilation, are essential when working with this compound.

Future research directions involving 2-Bromo-6-nitrobenzaldehyde are likely to focus on expanding its applications in medicinal chemistry and materials science. The growing demand for sustainable chemical processes may drive investigations into greener synthetic routes for this intermediate. Additionally, computational modeling techniques are being increasingly employed to predict reactivity patterns and optimize synthetic strategies involving 2-Bromo-6-nitrobenzaldehyde, further enhancing its utility in drug discovery programs.

In conclusion,2-Bromo-6-nitrobenzaldehyde (CAS No. 20357-21-5) is a multifaceted compound with broad applications across multiple scientific disciplines. Its unique structural features make it an indispensable tool for chemists engaged in pharmaceutical synthesis, agrochemical development, and material innovation. As research continues to uncover new possibilities for this versatile intermediate，its significance is poised to grow further，contributing to advancements that benefit society.

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