7-(Hydroxymethyl)isoquinoline: Properties & Lab Use FAQ

7-(Hydroxymethyl)isoquinoline is a hydroxymethyl-functionalized isoquinoline heterocycle that serves as a versatile synthetic building block for the preparation of more complex nitrogen-containing compounds in medicinal and synthetic chemistry research.

Chemical Name

7-(Hydroxymethyl)isoquinoline

SKU

M726430

Molecular Formula

C10H9NO

Core Structure

Isoquinoline ring bearing a –CH2OH substituent at the 7-position

Key Functional Group

Primary benzylic alcohol (–CH2OH) on an aromatic nitrogen heterocycle

Typical Application

Synthetic intermediate for drug discovery and heterocyclic chemistry

What Is 7-(Hydroxymethyl)isoquinoline?

7-(Hydroxymethyl)isoquinoline is an organic heterocyclic compound consisting of an isoquinoline bicyclic aromatic ring system with a hydroxymethyl (–CH2OH) group attached at the 7-position. The isoquinoline core is a benzopyridine isomer in which the nitrogen atom is located at position 2 of the fused ring system. The appended primary benzylic alcohol introduces a reactive handle that significantly broadens the compound's utility as a synthetic building block compared with unsubstituted isoquinoline.

Because the –CH2OH group can be readily oxidized, esterified, etherified, or converted to a leaving group, 7-(Hydroxymethyl)isoquinoline occupies a strategically important position in the synthesis of isoquinoline-containing pharmaceuticals, agrochemicals, and functional materials.

Key Physicochemical Properties

7-(Hydroxymethyl)isoquinoline has the molecular formula C₁₀H₉NO and a molecular weight of approximately 159.19 g/mol. The compound combines the aromatic, mildly basic isoquinoline nitrogen (pK_a of conjugate acid ~5.4 for the isoquinoline class) with the polarity introduced by the hydroxymethyl substituent, resulting in a molecule that is more hydrophilic than the parent isoquinoline.

The benzylic alcohol is expected to be a solid or low-melting solid at room temperature, with solubility in polar organic solvents such as methanol, ethanol, dimethyl sulfoxide (DMSO), and dichloromethane. Limited solubility in non-polar solvents such as hexane is anticipated. Researchers should verify the exact melting point and solubility profile from the certificate of analysis supplied with each lot.

Storage, Handling, and Safety

Storage: Store 7-(Hydroxymethyl)isoquinoline in a tightly sealed container in a cool, dry, well-ventilated area away from light and moisture. A refrigerated environment (2–8 °C) is generally recommended for long-term stability of benzylic alcohol-containing heterocycles. Always check the product label and safety data sheet (SDS) for lot-specific recommendations.

Handling: Use appropriate personal protective equipment (PPE) including chemical-resistant gloves, safety goggles, and a laboratory coat. Handle in a well-ventilated fume hood. Avoid inhalation of dust or aerosols. Wash hands thoroughly after handling.

Safety: As with most nitrogen-containing aromatic heterocycles, 7-(Hydroxymethyl)isoquinoline should be treated as a potential irritant. Consult the SDS before use. Dispose of waste in accordance with local environmental regulations.

Applications in Synthesis and Research

The bifunctional nature of 7-(Hydroxymethyl)isoquinoline — combining an aromatic nitrogen heterocycle with a reactive primary alcohol — makes it a valuable intermediate in several research contexts:

• Medicinal chemistry: The isoquinoline scaffold appears in numerous bioactive natural products and approved drugs. The 7-hydroxymethyl handle enables coupling to other pharmacophoric fragments via esterification, etherification, or Mitsunobu reactions, facilitating structure–activity relationship (SAR) studies.
• Prodrug design: The benzylic alcohol can be acylated to produce prodrug esters that may release the parent alcohol under physiological conditions.
• Ligand synthesis: Isoquinoline nitrogen atoms are useful metal-coordination sites; the additional –CH2OH group can be further elaborated into phosphine, amine, or other donor groups to create multidentate ligands for catalysis.
• Fluorescent probes and materials: Isoquinoline derivatives have been explored as fluorescent scaffolds; the hydroxymethyl group offers a conjugation point for attachment to surfaces or other chromophores.

Ordering and Quality Information

7-(Hydroxymethyl)isoquinoline is available from Aladdin Scientific under SKU M726430. When placing an order, please reference this SKU to ensure correct product identification. Each shipment is accompanied by a certificate of analysis (CoA) stating purity, appearance, and characterization data for the specific lot.

For questions regarding bulk quantities, custom packaging, or technical specifications, contact Aladdin Scientific's technical support or your regional sales representative. Current pricing, available pack sizes, and stock status can be found on the Aladdin Scientific website product page.

Frequently asked questions

What is the molecular formula and molecular weight of 7-(Hydroxymethyl)isoquinoline?

7-(Hydroxymethyl)isoquinoline has the molecular formula C10H9NO and a molecular weight of approximately 159.19 g/mol. Please confirm the exact value against the certificate of analysis provided with your specific lot (SKU M726430).

How should 7-(Hydroxymethyl)isoquinoline be stored to maintain stability?

Store the compound in a tightly sealed container at 2–8 °C, away from light, moisture, and incompatible materials. Polar organic solvents such as DMSO or ethanol can be used to prepare stock solutions; aliquot and freeze stock solutions to minimize freeze–thaw degradation. Always refer to the product SDS for authoritative storage guidance.

What reactions can be performed with the hydroxymethyl group of 7-(Hydroxymethyl)isoquinoline?

The primary benzylic –CH2OH group is highly versatile: it can be oxidized to an aldehyde or carboxylic acid, esterified or etherified with appropriate reagents, converted to a halide or mesylate/tosylate leaving group for nucleophilic substitution, or coupled via Mitsunobu conditions. These transformations make 7-(Hydroxymethyl)isoquinoline a flexible building block for drug discovery and materials science applications.

In which solvents does 7-(Hydroxymethyl)isoquinoline dissolve readily?

The compound is expected to dissolve readily in polar organic solvents including DMSO, methanol, ethanol, and dichloromethane, owing to the combined polarity of the isoquinoline nitrogen and the –CH2OH group. Solubility in water may be limited but enhanced at acidic pH due to protonation of the ring nitrogen. Solubility in non-polar solvents such as hexane is anticipated to be low. Verify solubility data with the CoA or by in-house testing.

What purity grade is Aladdin Scientific's 7-(Hydroxymethyl)isoquinoline (M726430) supplied at?

Purity information for SKU M726430 is provided on the certificate of analysis (CoA) accompanying each lot. For the most accurate and lot-specific purity data, please refer to the CoA available on the Aladdin Scientific website or contact technical support directly.

References

1. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. General reference for reactions of benzylic alcohols and heterocyclic chemistry.
2. Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications, 3rd ed.; Wiley-VCH: Weinheim, 2012. Reference for isoquinoline chemistry and reactivity.

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