Compound Overview and Chemical Properties

Methyl 2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylate (Aladdin SKU: M724940) is a member of the benzo[b][1,4]oxazine family. The compound features a bicyclic ring system in which a dihydro-oxazinone ring is fused to a benzene ring, with a methyl substituent at the 2-position and a methyl ester group at the 6-position of the aromatic ring. The lactam nitrogen (N-4) bears a free NH, making it amenable to N-alkylation, N-acylation, and other functionalization reactions. The ester moiety at C-6 provides a versatile handle for further elaboration via hydrolysis, amide coupling, or reduction. These combined features make the compound a valuable bifunctional scaffold in the construction of pharmacologically relevant heterocycles.

Safety and Handling Precautions

Before working with this compound, consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific. Standard laboratory precautions for fine organic chemicals apply:

• Personal Protective Equipment (PPE): Wear nitrile gloves, a laboratory coat, and safety spectacles at all times during handling.
• Ventilation: Handle the compound in a well-ventilated fume hood to minimise inhalation of dust or vapours.
• Skin and eye contact: In the event of skin or eye contact, flush immediately with copious water for at least 15 minutes and seek medical advice.
• Storage: Store in a tightly sealed container in a cool, dry location away from direct light, sources of ignition, and incompatible materials. Specific storage temperature should be confirmed from the product label and SDS.
• Waste disposal: Dispose of waste in accordance with local regulations for organic chemical waste.

Note: Specific hazard classifications, GHS pictograms, and first-aid measures must be verified against the current Aladdin SDS prior to use.

Solution Preparation and General Handling Protocol

Follow the steps below for reproducible preparation of stock and working solutions:

1. Equilibration: Allow the sealed container to equilibrate to room temperature before opening, particularly if stored cold, to prevent condensation and moisture uptake.
2. Weighing: Tare a clean, dry vial or weigh boat. Weigh the required mass of compound on an analytical balance in a fume hood.
3. Solvent selection: The compound is expected to dissolve in common organic solvents such as dimethyl sulfoxide (DMSO), dichloromethane (DCM), ethyl acetate, and tetrahydrofuran (THF). Solubility in aqueous systems is anticipated to be limited due to the lipophilic bicyclic scaffold. Confirm solubility experimentally before preparing large batches.
4. Stock solution preparation: Add the chosen solvent in portions to the weighed compound, vortex or stir gently until complete dissolution is observed. Prepare stock solutions at a convenient concentration (e.g., 10–100 mM) and aliquot to minimise freeze–thaw cycles.
5. Filtration (if required): If particulates are observed, filter through a 0.2 µm PTFE syringe filter.
6. Labelling: Label each aliquot with compound name, SKU (M724940), concentration, solvent, preparation date, and preparer initials.
7. Storage of solutions: Store solutions at −20 °C under inert atmosphere (argon or nitrogen) if extended storage is required. Verify stability under chosen conditions experimentally.

All specific solubility data and stability windows should be verified experimentally; consult the SDS and product technical documentation for further guidance.

Typical Applications in Synthetic Chemistry

Methyl 2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylate serves as a versatile intermediate in organic synthesis. Representative applications include:

• N-Functionalisation: The NH lactam nitrogen can be alkylated using alkyl halides under basic conditions (e.g., K₂CO₃ in DMF) or acylated with acid chlorides or anhydrides to yield N-substituted derivatives with modified pharmacokinetic profiles.
• Ester hydrolysis and amide coupling: The methyl ester at C-6 can be hydrolysed to the corresponding carboxylic acid under standard saponification conditions (e.g., LiOH, THF/H₂O), providing a carboxylic acid handle for HATU- or EDC-mediated amide coupling reactions to introduce amine fragments.
• Reduction: The ester can be reduced to the corresponding benzyl alcohol using reagents such as LiAlH₄ or DIBAL-H, expanding the structural diversity accessible from this scaffold.
• Scaffold elaboration for medicinal chemistry: The benzoxazinone core is recognised in medicinal chemistry as a privileged scaffold present in bioactive molecules. Derivatives are explored in the context of enzyme inhibition and receptor modulation programmes.

Specific reaction conditions, yields, and biological data should be sourced from primary literature. Claims regarding bioactivity require experimental validation.

Quality Control and Analytical Characterisation

Aladdin Scientific supplies M724940 with lot-specific quality control data. Researchers are encouraged to perform in-house confirmation of compound identity and purity prior to use in critical experiments. Recommended analytical methods include:

• Thin-Layer Chromatography (TLC): Run on silica gel plates using an appropriate eluent system (e.g., ethyl acetate/hexane mixtures). Visualise under UV light (254 nm) or with appropriate staining reagents.
• ¹H and ¹³C NMR Spectroscopy: Confirm structural identity and assess purity. Expected diagnostic signals include the methine proton at C-2, NH proton, aromatic protons, and the methyl ester singlet. Deuterated solvents such as CDCl₃ or DMSO-d₆ are typically suitable.
• HPLC Purity Analysis: Reverse-phase HPLC (C18 column, UV detection at 254 nm or 220 nm) provides quantitative purity assessment. A purity of ≥95% is generally expected for research-grade material; verify against the Certificate of Analysis (CoA) supplied with each lot.
• Mass Spectrometry (MS): Confirm molecular ion consistent with the molecular formula. ESI-MS in positive or negative ion mode is typically applicable.

Specific NMR chemical shifts, exact mass values, and HPLC retention times should be obtained from the product CoA or characterised experimentally.