Production Method 1

18282-59-2

93361-94-5

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Nitric acid

Reference

Potential noncataleptic neuroleptic agents: 2,3-dichloro-10-[4-(2-hydroxyethyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin

Urban, Jiri; Dlabac, Antonin; Valchar, Martin; Protiva, Miroslav, Collection of Czechoslovak Chemical Communications, 1984, 49(4), 992-100

Production Method 2

18282-59-2

93361-94-5

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Water ;  0 °C
1.2 Reagents: Sulfuric acid ,  Nitric acid Solvents: Water ;  40 min, 0 °C; 0 °C → rt; 0.5 h, rt
1.3 Reagents: Water ;  cooled

Reference

Preparation of benzo[1,2,5]thiadiazoles as CCK2 modulators for treatment of gastrointestinal disorders, pain, and other conditions

, United States, , ,

1-Bromo-4,5-dichloro-2-nitrobenzene Raw materials

• 1-Bromo-3,4-dichlorobenzene

1-Bromo-4,5-dichloro-2-nitrobenzene Preparation Products

• 1-Bromo-4,5-dichloro-2-nitrobenzene (93361-94-5)

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• 3. An approach to biodegradable star polymeric architectures using disulfide coupling?
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• 5. An analysis of the WTC fires using CIB correlations and simple modeling
  JGQuintiere

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

Chemical Profile of 1-Bromo-4,5-dichloro-2-nitrobenzene (CAS No. 93361-94-5)

1-Bromo-4,5-dichloro-2-nitrobenzene, identified by its Chemical Abstracts Service (CAS) number 93361-94-5, is a halogenated aromatic compound that has garnered significant attention in the field of organic synthesis and pharmaceutical chemistry. This compound serves as a versatile intermediate in the preparation of various fine chemicals, agrochemicals, and potential pharmacological agents. Its unique structural features, comprising bromine and chlorine substituents on a nitro-substituted benzene ring, make it a valuable building block for further functionalization.

The molecular structure of 1-Bromo-4,5-dichloro-2-nitrobenzene consists of a benzene ring substituted with a nitro group at the 2-position, and bromine atoms at the 1-position, along with chlorine atoms at the 4- and 5-positions. This arrangement imparts distinct reactivity patterns, enabling its use in diverse synthetic transformations. The nitro group is a well-known electrophile, facilitating nucleophilic aromatic substitution reactions, while the halogen atoms can participate in cross-coupling reactions or serve as anchors for further derivatization.

In recent years, the pharmaceutical industry has shown increasing interest in halogenated aromatic compounds due to their role as key intermediates in drug development. The presence of multiple halogen atoms in 1-Bromo-4,5-dichloro-2-nitrobenzene enhances its utility in constructing complex molecular architectures. For instance, palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings can be employed to introduce aryl or heteroaryl groups at specific positions, expanding the compound's synthetic potential.

One of the most compelling applications of 1-Bromo-4,5-dichloro-2-nitrobenzene lies in its use as a precursor for biologically active molecules. Researchers have leveraged its structural framework to develop novel compounds with therapeutic properties. For example, derivatives of this compound have been investigated for their antimicrobial and antifungal activities. The nitro group can be reduced to an amine, which can then be further modified to produce bioactive scaffolds. Additionally, the halogen atoms provide handles for selective functionalization, allowing chemists to tailor the molecule for specific biological targets.

The agrochemical sector also benefits from the versatility of 1-Bromo-4,5-dichloro-2-nitrobenzene. Its structural motif is common in many herbicides and pesticides, where halogenated aromatic compounds exhibit potent activity against unwanted vegetation or pests. By modifying the substituents on the benzene ring, researchers can fine-tune the biological activity and environmental profile of these compounds. This adaptability makes 1-Bromo-4,5-dichloro-2-nitrobenzene a valuable asset in developing next-generation agrochemicals.

From a synthetic chemistry perspective, 1-Bromo-4,5-dichloro-2-nitrobenzene offers unique opportunities for exploring new reaction pathways and methodologies. The combination of electron-withdrawing nitro and electron-releasing halogen groups creates a dynamic interplay that influences reaction outcomes. For instance, directed ortho-metalation strategies can be utilized to introduce various functional groups at specific positions on the benzene ring. This approach has enabled the synthesis of complex molecules that would be otherwise challenging to access.

The growing interest in sustainable chemistry has also influenced the use of 1-Bromo-4,5-dichloro-2-nitrobenzene. Researchers are increasingly focusing on developing greener synthetic routes that minimize waste and reduce hazardous byproducts. Catalytic methods and solvent-free reactions are being explored to enhance efficiency and environmental compatibility. These efforts align with global initiatives to promote sustainable chemical manufacturing practices.

In conclusion, 1-Bromo-4,5-dichloro-2-nitrobenzene (CAS No. 93361-94-5) is a multifaceted compound with broad applications across pharmaceuticals and agrochemicals. Its unique structural features enable diverse synthetic transformations, making it an indispensable intermediate in modern organic synthesis. As research continues to uncover new methodologies and applications, this compound will undoubtedly remain a cornerstone in the development of innovative chemical solutions.

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