Methyl 4-amino-3-bromobenzoate
[CAS# 106896-49-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Methyl ester compound
• Name: Methyl 4-amino-3-bromobenzoate
• Molecular Formula: C₈H₈BrNO₂
• Molecular Weight: 230.06
• CAS Registry Number: 106896-49-5
• EC Number: 628-549-7
• SMILES: COC(=O)C1=CC(=C(C=C1)N)Br

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Melting point: 104-108 ºC (Expl.)
• Index of Refraction: 1.601, Calc.^*
• Boiling Point: 334.2±22.0 ºC (760 mmHg), Calc.^*
• Flash Point: 155.9±22.3 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Hazard Statements: H301-H319
• Precautionary Statements: P264-P264+P265-P270-P280-P301+P316-P305+P351+P338-P321-P330-P337+P317-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H301
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 2811

Discovory and Applicatios

Methyl 4-amino-3-bromobenzoate is an aromatic compound that features a bromine atom, an amino group, and an ester functional group attached to a benzene ring. This multifunctional compound is widely used in organic synthesis due to its reactivity and structural versatility. It plays a crucial role in the development of advanced materials, pharmaceutical intermediates, and dyes.

The synthesis of methyl 4-amino-3-bromobenzoate typically begins with the bromination of methyl 4-aminobenzoate. This process introduces a bromine atom at the meta position relative to the amino group. Brominating agents such as bromine in acetic acid or N-bromosuccinimide (NBS) are commonly used to achieve high selectivity. Alternative synthesis routes involve functional group transformations starting from appropriately substituted benzoates.

Methyl 4-amino-3-bromobenzoate serves as a key intermediate in pharmaceutical research, particularly in the production of bioactive molecules. The bromine atom allows for further functionalization through cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig coupling. These reactions enable the incorporation of diverse substituents, facilitating the development of compounds with specific therapeutic properties. Additionally, the amino group can be modified through acylation or alkylation, expanding the compound's utility in drug discovery.

In the field of materials science, methyl 4-amino-3-bromobenzoate is used as a precursor for synthesizing advanced polymers and functional materials. The compound's aromatic core and functional groups contribute to the mechanical strength, thermal stability, and optical properties of the resulting materials. Its applications include coatings, electronic components, and specialty resins.

Methyl 4-amino-3-bromobenzoate is also valued in dye chemistry. The combination of an amino group and an aromatic ester facilitates the synthesis of chromophores with specific color properties. These dyes are used in textiles, printing, and analytical applications.

Recent research has focused on optimizing the synthesis of methyl 4-amino-3-bromobenzoate through green chemistry methods, such as solvent-free reactions and the use of recyclable catalysts. Additionally, its role in synthesizing novel heterocyclic compounds has expanded its importance in medicinal chemistry and agrochemical development.

References

2021. A Practical Procedure for Regioselective Bromination of Anilines. Synthesis.
DOI: 10.1055/a-1441-3236

2016. Recent Advances in Bromination of Aromatic and Heteroaromatic Compounds. Synthesis.
DOI: 10.1055/s-0035-1561503

2014. One-Step Synthesis of Quinolines via Palladium-Catalyzed Cross-Coupling of Cyclopropanols with Unprotected ortho-Bromoanilines. Synlett.
DOI: 10.1055/s-0034-1378613