(2-Methoxy-5-nitrophenyl)methanol: Properties & Lab Uses
(2-Methoxy-5-nitrophenyl)methanol: Properties & Lab Uses
(2-Methoxy-5-nitrophenyl)methanol is an aromatic benzyl alcohol derivative bearing both a methoxy and a nitro substituent on the phenyl ring, making it a versatile intermediate in organic synthesis and pharmaceutical research.
- IUPAC Name
- (2-Methoxy-5-nitrophenyl)methanol
- SKU
- M728946
- Molecular Formula
- C8H9NO4
- Molecular Weight
- 183.16 g/mol
- Functional Groups
- Benzyl alcohol (–CH2OH), methoxy (–OCH3), nitro (–NO2)
- Supplier
- Aladdin Scientific
Chemical Identity and Structure
(2-Methoxy-5-nitrophenyl)methanol (CAS registry; SKU M728946) is a substituted benzyl alcohol in which a methoxy group occupies the ortho position and a nitro group occupies the para position relative to the hydroxymethyl (–CH2OH) substituent. This arrangement creates an electron-rich oxygen donor (methoxy) and a strong electron-withdrawing group (nitro) on the same aromatic ring, conferring distinct reactivity profiles relevant to nucleophilic and electrophilic transformations.
The molecular formula is C8H9NO4 with a molecular weight of approximately 183.16 g/mol. The compound is typically encountered as a crystalline solid and should be stored in a cool, dry environment away from strong oxidizers and reducing agents, consistent with standard handling of nitroaromatic compounds.
Synthesis Relevance and Reactivity
(2-Methoxy-5-nitrophenyl)methanol serves as a key building block in the preparation of more complex aromatic scaffolds. The benzyl alcohol moiety can be oxidized to the corresponding aldehyde or carboxylic acid, or converted to benzyl halides and esters for use in protecting-group strategies and cross-coupling reactions. The nitro group offers a handle for reduction to the corresponding aniline, enabling access to aminobenzyl alcohol derivatives widely used in pharmaceutical synthesis.
The ortho-methoxy group can participate in directed metalation strategies, and its presence influences the regioselectivity of further electrophilic aromatic substitution. Researchers working on photoremovable protecting groups (caged compounds) may also find structural analogs of this scaffold relevant, as 2-nitrobenzyl alcohol derivatives are classical photolabile protecting groups in chemical biology.
Laboratory Applications
In medicinal chemistry, (2-Methoxy-5-nitrophenyl)methanol functions as an intermediate in the synthesis of nitro-substituted aromatic compounds that are screened for biological activity. The nitro group's ready convertibility to an amine allows for efficient structure–activity relationship (SAR) exploration around the aminobenzyl pharmacophore.
In material science and dye chemistry, methoxy- and nitro-substituted aromatic alcohols can serve as precursors to chromophoric systems and ligands for coordination chemistry. The compound may also be employed as a reference standard or calibration reagent in analytical method development.
Handling, Safety, and Storage
As a nitroaromatic compound, (2-Methoxy-5-nitrophenyl)methanol should be handled with standard laboratory precautions. Personnel should wear appropriate personal protective equipment (PPE) including gloves, safety glasses, and a lab coat. Work should be conducted in a well-ventilated area or under a fume hood.
The compound should be stored in a tightly sealed container in a cool, dry location, segregated from strong oxidizing and reducing agents. Users should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for specific hazard classifications, first-aid measures, and disposal procedures compliant with local regulations. Nitroaromatic compounds may present environmental hazards and should be disposed of through approved chemical waste channels.
Frequently asked questions
What is (2-Methoxy-5-nitrophenyl)methanol used for in organic synthesis?
(2-Methoxy-5-nitrophenyl)methanol is primarily used as a synthetic intermediate. Its benzyl alcohol group can be oxidized, halogenated, or esterified, while the nitro group can be reduced to an amine, providing versatile entry points into more complex molecular architectures relevant to medicinal chemistry and material science.
How should (2-Methoxy-5-nitrophenyl)methanol be stored?
The compound should be stored in a tightly sealed container in a cool, dry place, away from strong oxidizers and reducing agents. Always refer to the Aladdin Scientific SDS for the most current and specific storage recommendations.
Is (2-Methoxy-5-nitrophenyl)methanol related to photolabile protecting group chemistry?
Structurally, this compound belongs to the 2-nitrobenzyl alcohol family, which is well established in photolabile (caged) protecting group chemistry used in chemical biology. While the direct photochemical behavior of this specific compound should be verified experimentally, its scaffold is closely related to classical o-nitrobenzyl photocages.
What is the molecular weight of (2-Methoxy-5-nitrophenyl)methanol?
The molecular weight of (2-Methoxy-5-nitrophenyl)methanol is approximately 183.16 g/mol, with molecular formula C8H9NO4.
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for aromatic substitution and functional group interconversion.
- Klán, P. et al. Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy. Chemical Reviews. General reference for o-nitrobenzyl photocage chemistry.
- Aladdin Scientific. Product page for (2-Methoxy-5-nitrophenyl)methanol, SKU M728946.
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