2-Methyl-6-nitro-1H-indole: Properties, Uses & FAQs

2-methyl-6-nitro-1H-indole is a nitro-substituted indole derivative widely used as a versatile heterocyclic building block in organic synthesis and medicinal chemistry research.

CAS Number

3484-17-1

Molecular Formula

C₉H₈N₂O₂

Molecular Weight

176.17 g/mol

Substitution Pattern

2-methyl group at C-2; nitro group at C-6 of the indole ring

Aladdin SKU

M176214

Compound Class

Nitroindole; bicyclic heteroaromatic

Overview and Chemical Identity

2-Methyl-6-nitro-1H-indole (SKU M176214) is a bicyclic heteroaromatic compound belonging to the indole family. Its structure consists of a benzene ring fused to a pyrrole ring, with a methyl substituent at the 2-position and a nitro (–NO₂) group at the 6-position of the benzene ring. The nitro group is a strong electron-withdrawing substituent that significantly alters the electronic density of the indole π-system, lowering the HOMO energy and modifying reactivity at the 3-position and nitrogen centre relative to unsubstituted indole. The 2-methyl group provides additional steric and electronic influence at the α-position of the pyrrole ring, blocking electrophilic attack at C-2 and directing synthetic transformations toward other positions.

These combined substitution effects make 2-methyl-6-nitro-1H-indole a distinctive scaffold with tunable reactivity, distinguishing it from simpler indoles and making it attractive for targeted synthetic sequences in drug discovery and materials research.

Physical Properties and Handling

2-Methyl-6-nitro-1H-indole is typically obtained as a solid at room temperature. The nitro group confers a characteristic pale-yellow to yellow colouration. Key physical parameters (molecular weight 176.17 g/mol, molecular formula C₉H₈N₂O₂) are confirmed by the structural assignment. Specific melting point, solubility values, and purity specifications for lot M176214 should be confirmed against the current Certificate of Analysis (CoA) available from Aladdin Scientific, as these figures may vary by lot.

Solubility guidance: Indole derivatives bearing electron-withdrawing nitro groups generally show moderate solubility in polar aprotic solvents such as dimethyl sulfoxide (DMSO) and N,N-dimethylformamide (DMF), and limited solubility in water. Dissolution in DMSO at stock concentrations followed by aqueous dilution is a common approach for biological assays.

Handling precautions: Standard laboratory precautions for fine organic chemicals apply. Work in a well-ventilated fume hood, wear appropriate PPE (gloves, lab coat, eye protection), and consult the Safety Data Sheet (SDS) before use. Nitroaromatic compounds should be handled with awareness of potential skin and eye irritancy.

Storage Conditions and Stability

For optimal long-term stability, 2-methyl-6-nitro-1H-indole should be stored in a tightly sealed container, protected from light, heat, and moisture. Cool, dry storage conditions (typically 2–8 °C or room temperature in a desiccated environment, per CoA recommendation) help prevent degradation of the nitro functionality and the indole NH. Exposure to strong reducing agents or prolonged UV irradiation should be avoided, as these can chemically alter nitroaromatic compounds.

Always confirm specific storage requirements for lot M176214 by referring to the product label and current CoA from Aladdin Scientific. Shelf-life data, where available, will be stated on the CoA.

Research and Synthetic Applications

The indole scaffold is one of the most prevalent heterocyclic motifs in bioactive natural products and pharmaceuticals. 2-Methyl-6-nitro-1H-indole combines several features useful to synthetic chemists:

• Medicinal chemistry building block: The electron-deficient nature introduced by the 6-nitro group can modulate binding interactions with biological targets. The nitro group may also serve as a handle for further functionalization, notably reduction to the corresponding 6-aminoindole derivative, which is itself a valuable intermediate for amide couplings, reductive aminations, and heterocycle formation.
• Cross-coupling partner: The C-3 position of 2-substituted indoles remains accessible for electrophilic or metal-catalysed reactions. N-protected variants can participate in palladium-catalysed cross-coupling reactions.
• Fluorescence and materials research: Nitroindoles exhibit photophysical properties of interest in the development of fluorescent probes and organic electronic materials; researchers have investigated nitroindole derivatives as fluorescence quenchers and charge-transfer components.
• Synthetic intermediate: The compound serves as a starting material or intermediate in multi-step syntheses targeting complex indole-containing natural product analogues and pharmaceutical candidates.

Researchers should consult the primary literature for specific reaction conditions and yields relevant to their synthetic targets.

Ordering, Purity and Quality Specifications

2-Methyl-6-nitro-1H-indole is available from Aladdin Scientific under SKU M176214. Purity grade, available pack sizes, and current pricing are listed on the product page. Each lot is supported by a Certificate of Analysis documenting purity (typically assessed by HPLC or GC), identity confirmation (NMR or MS), and relevant physical data.

To place an order, visit the Aladdin Scientific website and search by product name or SKU M176214. For bulk quantities, custom purity grades, or specific analytical requirements, contact the Aladdin Scientific sales or technical support team directly. Quantity discounts and institutional pricing may be available.

If you require a Safety Data Sheet (SDS) for risk assessment or regulatory compliance, this document is available for download from the product page or upon request from customer service.

Frequently asked questions

What is the CAS number for 2-methyl-6-nitro-1H-indole?

The CAS registry number for 2-methyl-6-nitro-1H-indole is 3484-17-1. At Aladdin Scientific it is catalogued under SKU M176214. Always verify the CAS number against the product label or CoA when ordering to ensure you receive the correct compound.

What solvents are suitable for dissolving 2-methyl-6-nitro-1H-indole?

Based on general properties of electron-deficient nitroindole derivatives, polar aprotic solvents such as DMSO and DMF are expected to provide good solubility. Solubility in water is likely to be low. Specific solubility data for lot M176214 should be confirmed from the CoA or by in-house testing, as exact values are not provided in the current source material.

Can the nitro group of 2-methyl-6-nitro-1H-indole be reduced to an amine?

Yes, nitro groups on aromatic rings are routinely reduced to primary amines using reagents such as iron or tin in acidic media, catalytic hydrogenation (H₂/Pd-C), or transfer hydrogenation conditions. Reduction of the 6-nitro group would yield 2-methyl-1H-indol-6-amine, a valuable intermediate for further derivatisation. Researchers should consult the primary literature for optimised conditions compatible with the indole NH and 2-methyl group.

How should 2-methyl-6-nitro-1H-indole be stored to maintain stability?

Store 2-methyl-6-nitro-1H-indole in a tightly sealed container, protected from light, moisture, and heat. Cool, dry conditions are generally recommended for nitroindole derivatives. Refer to the Aladdin Scientific CoA and SDS for lot-specific storage temperature recommendations and shelf-life information.

What is the molecular weight and molecular formula of 2-methyl-6-nitro-1H-indole?

2-Methyl-6-nitro-1H-indole has the molecular formula C₉H₈N₂O₂ and a molecular weight of 176.17 g/mol. These values are derived from its structural composition: the indole bicyclic core plus a methyl group at C-2 and a nitro group at C-6.

References

1. Aladdin Scientific product page: 2-Methyl-6-nitro-1H-indole, SKU M176214. Aladdin Scientific, accessed 2024.
2. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (General indole chemistry reference.)

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