Methyl 2-bromomethyl-3-nitrobenzoate
[CAS# 98475-07-1]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon nitrite
• Name: Methyl 2-bromomethyl-3-nitrobenzoate
• Synonyms: 2-Bromomethyl-3-nitrobenzoic acid methyl ester
• Molecular Formula: C₉H₈BrNO₄
• Molecular Weight: 274.07
• CAS Registry Number: 98475-07-1
• EC Number: 619-354-8
• SMILES: COC(=O)C1=C(C(=CC=C1)[N+](=O)[O-])CBr

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Boiling point: 370.9±32.0 ºC 760 mmHg (Calc.)^*
• Flash point: 178.1±25.1 ºC (Calc.)^*
• Index of refraction: 1.594 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 DangerGHS05
• Hazard Statements: H290-H314-H315-H318-H319-H335-H340-H350-H373
• Precautionary Statements: P203-P234-P260-P261-P264-P264+P265-P271-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P318-P319-P321-P332+P317-P337+P317-P362+P364-P363-P390-P403+P233-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Specific target organ toxicity - single exposure	STOT SE	3	H335
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Serious eye damage	Eye Dam.	1	H318
Germ cell mutagenicity	Muta.	1B	H340
Skin corrosion	Skin Corr.	1C	H314
Carcinogenicity	Carc.	1B	H350

Discovory and Applicatios

Methyl 2-bromomethyl-3-nitrobenzoate is an organic compound with the molecular formula C8H8BrNO4. It consists of a benzoate ester group (-COOCH3) attached to a benzene ring, along with a bromomethyl group (-CH2Br) at the 2-position and a nitro group (-NO2) at the 3-position on the ring. This structure places it within the class of halogenated and nitro-substituted aromatic compounds.

The synthesis of methyl 2-bromomethyl-3-nitrobenzoate typically involves a series of reactions starting from 2-bromomethyl-3-nitrobenzoic acid or other similar precursors. The esterification step, where the carboxyl group (-COOH) of the benzoic acid is converted into a methyl ester group (-COOCH3), is typically carried out using methanol in the presence of a strong acid catalyst such as sulfuric acid or through direct esterification with methyl alcohol. The bromo and nitro groups on the benzene ring are already in place in the starting material, making it easier to produce the desired compound.

The compound is highly functionalized and, like other halogenated aromatic compounds, is quite reactive due to the presence of both the bromomethyl and nitro groups. The bromomethyl group, in particular, serves as an electrophilic center and can participate in nucleophilic substitution reactions, allowing for the introduction of various functional groups. This reactivity makes methyl 2-bromomethyl-3-nitrobenzoate a valuable intermediate in organic synthesis.

One of the key applications of methyl 2-bromomethyl-3-nitrobenzoate is in the synthesis of more complex organic molecules, including pharmaceuticals and agrochemicals. The bromomethyl group can undergo nucleophilic substitution with a variety of nucleophiles such as amines, alcohols, and thiols, enabling the introduction of new functional groups into the molecule. The presence of the nitro group may also impart certain electronic properties to the molecule, making it useful in the design of compounds with specific biological or chemical activities.

In addition to pharmaceutical applications, methyl 2-bromomethyl-3-nitrobenzoate can be used as a building block in materials science. The nitro and bromomethyl groups can influence the electronic and optical properties of the compound, making it useful for the development of new materials, such as sensors, polymers, and organic semiconductors. By functionalizing the molecule further, researchers can tailor its properties for specific applications in electronics, photonics, and sensing technologies.

Methyl 2-bromomethyl-3-nitrobenzoate can also find use in the synthesis of fluorescent compounds. The nitro group is an electron-withdrawing group that can modify the electronic structure of the aromatic ring, which may affect the light absorption and emission properties of the molecule. As a result, derivatives of this compound could potentially be used in fluorescence-based applications, such as in organic light-emitting diodes (OLEDs) or as dyes in various sensing technologies.

Despite its useful applications, methyl 2-bromomethyl-3-nitrobenzoate should be handled with care due to its reactive nature. The bromomethyl group can be hazardous, as it may cause irritation or burns upon contact with the skin, eyes, or mucous membranes. Proper safety precautions, including wearing gloves, goggles, and protective clothing, are essential when working with this compound. It is also important to handle the compound in a well-ventilated area to avoid inhalation of any potentially harmful vapors.

In summary, methyl 2-bromomethyl-3-nitrobenzoate is a versatile compound used in the synthesis of various organic compounds. Its reactivity, due to the bromomethyl and nitro groups, makes it a valuable intermediate in the development of pharmaceuticals, agrochemicals, and materials. Its application potential extends to fluorescence-based technologies, and it serves as a key building block in organic synthesis. However, as with any reactive chemical, appropriate safety measures should be observed during handling to minimize risks to health and safety.

References

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DOI: 10.1007/s10593-015-1670-0

2022. Experimental design optimization for the synthesis of lenalidomide nitro precursor. Research on Chemical Intermediates, 48(12).
DOI: 10.1007/s11164-022-04869-5