1-Bromo-4-nitrobenzene
[CAS# 586-78-7]

Identification

• Classification: Pharmaceutical intermediate >> OLED material intermediate
• Name: 1-Bromo-4-nitrobenzene
• Synonyms: 4-Bromo-1-nitrobenzene
• Molecular Formula: C₆H₄BrNO₂
• Molecular Weight: 202.01
• CAS Registry Number: 586-78-7
• EC Number: 209-583-8
• SMILES: C1=CC(=CC=C1[N+](=O)[O-])Br

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*, 1.948 g/mL (Expl.)
• Melting point: 124-126 °C (Expl.)
• Index of Refraction: 1.606, Calc.^*
• Boiling Point: 252.6±13.0 °C (760 mmHg), Calc.^*, 255-256 °C (Expl.)
• Flash Point: 106.6±19.8 °C, Calc.^*
• Water solubility: insoluble

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335-H373
• Safety Statements: P260-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H311

• Transport Information: UN 3459

Discovery and Applications

1-Bromo-4-nitrobenzene is an organic compound consisting of a benzene ring substituted with a bromine atom at the first position and a nitro group at the fourth position. This compound is an important intermediate in organic synthesis, particularly in the preparation of various pharmaceuticals, agrochemicals, and other specialty chemicals.

The synthesis of 1-bromo-4-nitrobenzene was first reported in the mid-20th century as part of the broader interest in halogenated aromatic compounds. The compound is characterized by the presence of both a bromine atom and a nitro group on the benzene ring, which significantly influences its chemical reactivity, particularly in nucleophilic aromatic substitution reactions.

1-Bromo-4-nitrobenzene is primarily used as an intermediate in the synthesis of more complex organic molecules. Its bromine atom makes it an ideal candidate for substitution reactions, particularly those involving nucleophilic attack on the carbon-bromine bond. The nitro group, being an electron-withdrawing group, further activates the ring toward nucleophilic substitution, which is useful in the synthesis of a wide range of compounds.

One notable application of 1-bromo-4-nitrobenzene is in the synthesis of biologically active molecules. It is employed in the preparation of various pharmaceuticals and agrochemicals, where the compound's reactivity allows for the introduction of different functional groups into the benzene ring. The nitro group can be selectively reduced to an amine, enabling further functionalization and modification to create new drugs and therapeutic agents.

The compound is also used in the preparation of polycyclic aromatic compounds, which have applications in materials science, particularly in the development of organic semiconductors. Organic semiconductors are materials used in the fabrication of organic light-emitting diodes (OLEDs), organic solar cells, and organic field-effect transistors (OFETs). The synthesis of these materials often involves the use of halogenated aromatic compounds, such as 1-bromo-4-nitrobenzene, to construct larger, more complex aromatic structures with desired electronic properties.

In addition to its role in the synthesis of pharmaceuticals and materials, 1-bromo-4-nitrobenzene is also used in the development of new chemical reactions. It serves as a model compound in research on nucleophilic aromatic substitution and other organic transformations. Its well-established reactivity and the presence of both electron-withdrawing and halogen substituents on the benzene ring make it a valuable tool in the study of aromatic substitution mechanisms and the development of new synthetic methods.

Furthermore, 1-bromo-4-nitrobenzene is employed in the synthesis of various industrial chemicals, including those used in the production of dyes and pigments. The compound's ability to undergo substitution reactions with a range of nucleophiles makes it an important precursor in the chemical industry.

In summary, 1-bromo-4-nitrobenzene is a versatile and widely used intermediate in organic synthesis. Its applications span pharmaceuticals, materials science, agrochemicals, and the development of new chemical reactions. The compound's well-established reactivity, particularly in nucleophilic aromatic substitution, has made it an important building block in the synthesis of a variety of valuable chemicals.

References

2022. Pd-Fe bimetallic nanoparticles anchored on N-doped carbon-modified graphene for efficient catalytic organic reactions. Carbon Letters, 33(3).
DOI: 10.1007/s42823-022-00404-z

2023. Biomacromolecule supported N-heterocyclic carbene-palladium(II) as a novel catalyst for Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions. Cellulose, 30(12).
DOI: 10.1007/s10570-023-05323-4

2024. Recent synthetic strategies for N-arylation of pyrrolidines: a potential template for biologically active molecules. Molecular Diversity.
DOI: 10.1007/s11030-024-10924-7