1-Bromo-2-methoxy-3-nitrobenzene
[CAS# 98775-19-0]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon nitrite
• Name: 1-Bromo-2-methoxy-3-nitrobenzene
• Molecular Formula: C₇H₆BrNO₃
• Molecular Weight: 230.95
• CAS Registry Number: 98775-19-0
• EC Number: 807-179-1
• SMILES: COC1=C(C=CC=C1Br)[N+](=O)[O-]

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.581, Calc.^*
• Boiling Point: 296.4±20.0 °C (760 mmHg), Calc.^*
• Flash Point: 133.1±21.8 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H332
• Safety Statements: P261-P264-P270-P271-P280-P301+P317-P302+P352-P304+P340-P317-P321-P330-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332

Discovery and Applications

1-Bromo-2-methoxy-3-nitrobenzene is an organic compound that is part of the class of substituted nitrobenzene derivatives. It consists of a benzene ring substituted with a bromine atom at the 1-position, a methoxy group (-OCH3) at the 2-position, and a nitro group (-NO2) at the 3-position. This molecule is commonly used as an intermediate in organic synthesis, particularly in the production of other functionalized aromatic compounds.

The discovery of 1-bromo-2-methoxy-3-nitrobenzene lies within the broader field of substituted nitrobenzene compounds, which have been extensively studied for their diverse chemical reactivity and applications in various industries. Nitrobenzenes, as a class of compounds, are known for their role in the synthesis of pharmaceuticals, dyes, and agrochemicals, among other uses. The introduction of electron-donating and electron-withdrawing groups, such as the methoxy and nitro groups in this case, significantly alters the electronic properties of the benzene ring, making these compounds valuable intermediates for further functionalization.

The synthesis of 1-bromo-2-methoxy-3-nitrobenzene typically involves electrophilic aromatic substitution reactions. One common method is the bromination of 2-methoxy-3-nitrobenzenes, where bromine is introduced at the 1-position of the ring under controlled conditions. This synthetic route is well-established and has been documented in the chemical literature. The positioning of the substituents on the benzene ring influences the reactivity of the compound, particularly in subsequent substitution reactions.

1-Bromo-2-methoxy-3-nitrobenzene has applications in organic synthesis, especially in the preparation of more complex organic molecules. The presence of the bromo group allows for its use in cross-coupling reactions such as the Suzuki, Heck, and Stille reactions. These reactions enable the formation of carbon-carbon bonds, which are essential for the synthesis of more complex molecules with potential applications in pharmaceuticals and material science.

One notable application of 1-bromo-2-methoxy-3-nitrobenzene is in the synthesis of compounds with potential pharmaceutical activity. The nitro group is a common pharmacophore, and its presence in combination with other functional groups such as methoxy and bromine can lead to compounds with enhanced biological activity. The compound's reactivity also makes it a suitable starting material for the development of agrochemicals and dyes, where similar functional groups are often required.

Furthermore, 1-bromo-2-methoxy-3-nitrobenzene plays a role in materials science, particularly in the synthesis of organic electronic materials. The introduction of electron-withdrawing and electron-donating groups can influence the electronic properties of the compound, making it useful for the development of organic semiconductors, OLEDs (organic light-emitting diodes), and other organic electronic devices.

In conclusion, 1-bromo-2-methoxy-3-nitrobenzene is a versatile intermediate in organic synthesis, with established applications in pharmaceuticals, agrochemicals, dyes, and materials science. Its synthesis and reactivity have been well-documented, and it continues to be an important compound for the development of various organic materials and bioactive molecules.

References

1927. Eine molekulare Umlagerung bei der Darstellung des Tribrom-o-Anisidins auso-Nitroanisol. Monatshefte für Chemie und verwandte Teile anderer Wissenschaften, 48(1).
DOI: 10.1007/bf01518079

2011. Eltrombopag. Pharmaceutical Substances.
https://pharmaceutical-substances.thieme.com