Methyl 3-Hydroxy-5-Methoxybenzoate: Properties & Lab Use Guide

Methyl 3-hydroxy-5-methoxybenzoate is a bifunctional aromatic ester reagent bearing both a free phenolic hydroxyl group and a methoxy substituent, making it a versatile building block for organic synthesis and medicinal chemistry research.

Chemical Name

Methyl 3-hydroxy-5-methoxybenzoate

SKU

M191858

Molecular Formula

C9H10O4

Molecular Weight

182.17 g/mol

CAS Number

3709-44-2

Key Functional Groups

Phenolic hydroxyl (-OH), methoxy (-OCH3), methyl ester (-COOCH3)

Typical Application

Intermediate in organic synthesis, pharmaceutical research, and materials chemistry

Chemical Identity and Physical Properties

Methyl 3-hydroxy-5-methoxybenzoate (CAS 3709-44-2, SKU M191858) is a substituted benzoate ester with the molecular formula C₉H₁₀O₄ and a molecular weight of approximately 182.17 g/mol. Its aromatic ring carries three distinct substituents at the 1-, 3-, and 5-positions: a methyl ester group (–COOCH₃), a free phenolic hydroxyl group (–OH), and a methoxy group (–OCH₃). This meta-substituted pattern confers a high degree of symmetry and influences both the electronic properties of the ring and the compound's reactivity. The compound is typically a white to off-white crystalline solid at room temperature. It is generally soluble in common polar organic solvents such as methanol, ethanol, ethyl acetate, and dimethyl sulfoxide (DMSO), and has limited solubility in water. Researchers should verify specific purity, melting point, and solubility data from the certificate of analysis (CoA) supplied with each lot of M191858.

Research Applications and Synthetic Utility

The bifunctional nature of Methyl 3-hydroxy-5-methoxybenzoate makes it a valuable intermediate in multi-step organic synthesis. The free phenolic hydroxyl group is available for selective O-alkylation, O-acylation, etherification, or coupling reactions, while the methyl ester can undergo hydrolysis to the corresponding carboxylic acid, reduction to the benzyl alcohol, or conversion to amide derivatives. The methoxy group can, under forcing conditions, be demethylated to unmask a second hydroxyl group, providing further structural diversity.

In medicinal chemistry, phenolic methyl esters of this structural class have been employed as precursors to natural product analogues and as scaffolds for structure–activity relationship (SAR) studies. The electron-donating methoxy and hydroxyl groups modulate ring electron density, which can influence binding interactions with biological targets. In materials chemistry, such compounds have been explored as monomers or crosslinkers in the synthesis of functional polymers and resins. Researchers are encouraged to consult the primary literature for application-specific protocols before beginning synthetic work.

Handling, Storage, and Safety Guidelines

As with all laboratory chemicals, Methyl 3-hydroxy-5-methoxybenzoate should be handled in accordance with standard laboratory safety practices. Always consult the Safety Data Sheet (SDS) for M191858 before use, as it contains authoritative hazard classifications, first-aid measures, and disposal guidance specific to this compound.

Storage: Store the compound in a tightly sealed container, protected from light and moisture, at room temperature or as specified on the product label and CoA. Prolonged exposure to air and humidity may cause gradual degradation of phenolic reagents.

Personal Protective Equipment (PPE): Wear appropriate PPE including laboratory coat, chemical-resistant gloves, and safety glasses when weighing or handling the neat compound. Work in a well-ventilated area or fume hood to minimize inhalation exposure to fine particulates.

Waste Disposal: Dispose of waste material and used containers in accordance with local regulations governing aromatic organic compounds. Do not pour organic reagent waste down the drain.

Quality, Purity, and Procurement Guidance

Aladdin Scientific supplies Methyl 3-hydroxy-5-methoxybenzoate under SKU M191858. Purity specifications and analytical data, including results from techniques such as HPLC, GC, or NMR, are provided on the lot-specific certificate of analysis (CoA) available upon request or via the product page. Researchers should select the appropriate purity grade based on the sensitivity of their application: high-purity grades are recommended for biological assays and precise physicochemical measurements, while standard grades may be appropriate for exploratory synthetic work.

For bulk quantities, custom packaging, or enquiries regarding specific purity grades and analytical certificates, contact Aladdin Scientific's technical support or your regional sales representative. Proper lot-to-lot consistency is critical for reproducible research; always record the lot number in experimental notebooks and publications.

Frequently asked questions

What solvents are recommended for dissolving Methyl 3-hydroxy-5-methoxybenzoate?

Methyl 3-hydroxy-5-methoxybenzoate is generally soluble in polar organic solvents including methanol, ethanol, ethyl acetate, acetone, and DMSO. Solubility in water is limited due to the hydrophobic aromatic core. Always prepare a small test dissolution before committing to large-scale use, and refer to the lot CoA for confirmed solubility data.

How should Methyl 3-hydroxy-5-methoxybenzoate be stored to maintain stability?

The compound should be stored in a tightly closed container, away from light, heat, and moisture, at room temperature unless otherwise specified on the product label or CoA. Phenolic compounds can be susceptible to oxidative degradation upon prolonged exposure to air; therefore, minimizing headspace and using inert atmosphere storage for opened containers is advisable.

Can the free hydroxyl group of Methyl 3-hydroxy-5-methoxybenzoate be selectively functionalized?

Yes, the phenolic hydroxyl group at the 3-position can be selectively functionalized through reactions such as O-alkylation (e.g., using alkyl halides with a base), O-acylation, or Mitsunobu reactions, while the methyl ester group remains intact under mild conditions. Careful selection of reaction conditions and protecting group strategies is essential to achieve chemoselectivity when multiple reactive sites are present.

What analytical methods can be used to characterize Methyl 3-hydroxy-5-methoxybenzoate purity?

Common analytical methods include high-performance liquid chromatography (HPLC) with UV detection, gas chromatography (GC), and nuclear magnetic resonance (NMR) spectroscopy (1H and 13C). Mass spectrometry (MS) can confirm molecular identity. The lot-specific CoA from Aladdin Scientific will detail which methods were used and the corresponding purity values for SKU M191858.

References

1. Safety Data Sheet: Methyl 3-hydroxy-5-methoxybenzoate, Aladdin Scientific, SKU M191858. Consult current SDS for up-to-date hazard and handling information.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed. Wiley-Interscience, 1992. General reference for esterification, O-alkylation, and related reactions of phenolic compounds.
3. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed. Oxford University Press, 2012. Textbook reference for functional group transformations relevant to benzoate esters and phenols.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.