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Description
Methyl 2-Amino-4,5-dimethoxybenzoate from TCI is the methyl ester of anthranilic acid bearing two methoxy groups at the 4 and 5 positions of the benzene ring. The molecule combines three complementary functional groups: a primary aromatic amine, a methyl ester, and an electron-rich pair of methoxy substituents. This combination makes it a highly productive starting material for building amide bonds and nitrogen-containing heterocyclic rings. The 4,5-dimethoxy substitution pattern is also characteristic of many natural and synthetic bioactive compounds, so this material frequently serves as the most direct entry point toward such scaffolds.
The property that makes it a preferred choice is its tiered, easily controlled reactivity. The aromatic amine, positioned ortho to the ester, can be acylated, sulfonylated, diazotised, or coupled with activated carboxylic acids; once the amide has formed, the geometric proximity between the amide and the ester facilitates intramolecular cyclisation into quinazolinones and benzoxazinones. The two methoxy groups raise the electron density of the ring, which in turn influences the rate of electrophilic aromatic substitution and the spectroscopic characteristics of the resulting derivatives. The ester group itself remains available for further transformation, giving synthetic chemists several independent handles on a single small scaffold.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic synthesis, medicinal chemistry, and peptide chemistry, as well as in industrial R&D units developing new compound libraries. It is normally purchased in research-scale quantities for multi-step syntheses, method development, and the preparation of reference derivatives, where a well-defined trifunctional starting material shortens the route and reduces the number of protection and deprotection steps required.
Laboratory Applications
- Amide bond formation: the primary aromatic amine couples readily with activated carboxylic acids, making this a reliable partner for building amide linkages in peptide chemistry work.
- Quinazolinone synthesis: after acylation of the amine, the neighbouring ester group allows intramolecular cyclisation, giving direct access to nitrogen-containing quinazolinone ring systems.
- Benzoxazinone preparation: the ortho relationship between the amide and ester functions provides the geometry needed for ring closure into benzoxazinone scaffolds under standard conditions.
- Bioactive scaffold construction: the 4,5-dimethoxy substitution pattern found in many natural and synthetic bioactive compounds is already present, shortening routes toward such targets.
- Derivatisation and reference compound preparation: the amine can be sulfonylated or diazotised while the ester remains available, supporting the systematic preparation of structurally related derivatives.
Specifications
- Brand: TCI
- CAS Number: 26759-46-6
- Chemical Name: Methyl 2-Amino-4,5-dimethoxybenzoate
- Product Code: D2749
- Category: Chemistry > Chemical Biology > Peptide Chemistry
- Pack Sizes: available in research-scale laboratory pack sizes; please confirm the currently offered packaging when ordering
- Storage: store in a tightly closed original container under the conditions stated on the manufacturer's label and safety data sheet
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area away from direct sunlight, heat sources, and incompatible materials, following the conditions specified on the TCI label and safety data sheet. Keep the material in its original supplier container, or in a clean, chemically compatible, clearly labelled glass container if subdivision is necessary. Handle in a fume hood using safety goggles, gloves, and a laboratory coat, and avoid inhalation of dust and contact with skin and eyes. As an aromatic amine derivative, the material may be sensitive to prolonged exposure to air and light, so minimise open handling time and reseal promptly after weighing. Review the current safety data sheet before use and dispose of residues and contaminated materials through the laboratory's regulated chemical waste stream.
