2-Methyl-3-hexanol: Properties, Uses & Lab Guide

2-Methyl-3-hexanol is a branched-chain secondary aliphatic alcohol valued in organic chemistry research for its chiral center, moderate boiling point, and versatility as a synthetic building block and analytical reference standard.

Molecular Formula

C₇H₁₆O

Molecular Weight

116.20 g/mol

Alcohol Class

Secondary (branched-chain) aliphatic alcohol

Chiral Centers

1 (C-3)

CAS Number

617-29-8

Appearance

Colorless liquid

Aladdin SKU

M352404

Chemical Identity and Physical Properties

2-Methyl-3-hexanol (CAS 617-29-8) is a seven-carbon, branched-chain secondary alcohol with the molecular formula C₇H₁₆O and a molecular weight of approximately 116.20 g/mol. The compound features a hydroxyl group at the C-3 position and a methyl branch at C-2, generating a single stereogenic center at C-3. As a result, two enantiomers exist: (R)- and (S)-2-methyl-3-hexanol.

Typical physical characteristics of 2-Methyl-3-hexanol include a colorless, clear liquid appearance with a mild, characteristic alcoholic odor. The compound is sparingly soluble in water but miscible with common organic solvents such as ethanol, diethyl ether, and acetone, consistent with its amphiphilic character as a mid-chain alcohol.

Note: Specific numerical values for boiling point, density, refractive index, and flash point should be confirmed against the supplier certificate of analysis (CoA) or a validated physicochemical database, as these may vary with purity and measurement conditions.

Synthesis and Structural Context

2-Methyl-3-hexanol belongs to the broader family of branched aliphatic alcohols and can be obtained through several classical synthetic routes. A common laboratory approach involves the Grignard reaction: treatment of 2-methylpropanal (isobutyraldehyde) or a related aldehyde with an appropriate alkyl magnesium halide reagent, followed by aqueous workup, yields the secondary alcohol product. Alternatively, reduction of the corresponding branched ketone (e.g., 2-methyl-3-hexanone) using hydride reducing agents such as sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄) provides access to the racemic alcohol.

The presence of the chiral center at C-3 makes enantioselective synthesis approaches—such as asymmetric hydrogenation or enzymatic resolution—relevant for researchers requiring enantiomerically enriched material. Racemic 2-Methyl-3-hexanol serves as a useful starting material for further functionalization, including esterification, oxidation to the ketone, or dehydration to branched alkene products.

Research Applications

2-Methyl-3-hexanol finds utility across several domains of chemical and biochemical research:

• Organic Synthesis Building Block: The compound serves as a chiral or racemic starting material for the preparation of more complex molecules, including natural product analogs and pharmaceutical intermediates that incorporate a branched secondary alcohol motif.
• Analytical Reference Standard: Branched-chain alcohols including 2-Methyl-3-hexanol are used as reference compounds in gas chromatography (GC) method development and in the characterization of flavor, fragrance, and environmental samples where such alcohols occur as minor constituents.
• Structure–Activity Relationship (SAR) Studies: As a structurally defined secondary alcohol, it can be employed in SAR panels to investigate how branching, chain length, and stereochemistry influence biological activity or physicochemical parameters.
• Solvent and Co-solvent Investigations: Mid-chain aliphatic alcohols are studied for their solvation properties, hydrogen-bonding capacity, and behavior in mixed solvent systems relevant to formulation research.

Researchers should consult primary literature and validate specific applications before use in regulated or critical assays.

Safe Handling, Storage, and Regulatory Considerations

As with most low-molecular-weight aliphatic alcohols, 2-Methyl-3-hexanol should be handled with standard laboratory precautions:

• Personal Protective Equipment (PPE): Wear chemical-resistant gloves, safety glasses or goggles, and a laboratory coat. Work in a well-ventilated area or fume hood to minimize inhalation exposure.
• Flammability: Branched aliphatic alcohols are typically flammable liquids. Keep away from open flames, sparks, and other ignition sources. Specific flash point data should be confirmed on the product Safety Data Sheet (SDS).
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated location away from oxidizing agents and heat sources. Recommended storage temperature is typically ambient or slightly below; confirm with the product SDS and CoA.
• Disposal: Dispose of waste material in accordance with local, regional, and national regulations governing flammable organic solvents.

Always consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific before use. SDS documents contain authoritative hazard classifications, first-aid measures, and transport information specific to each product lot.

Frequently asked questions

What is the CAS number for 2-Methyl-3-hexanol?

The CAS Registry Number for 2-Methyl-3-hexanol is 617-29-8. This identifier can be used to confirm the compound across supplier catalogues, safety databases, and chemical literature.

Is 2-Methyl-3-hexanol a chiral compound?

Yes. 2-Methyl-3-hexanol possesses one stereogenic center located at the C-3 carbon, giving rise to two enantiomers: the (R)- and (S)-forms. The commercially supplied material from Aladdin Scientific (SKU M352404) is racemic unless otherwise specified; researchers requiring enantiopure material should request specific stereochemical details.

What solvents are compatible with 2-Methyl-3-hexanol?

2-Methyl-3-hexanol is miscible with common organic solvents including ethanol, diethyl ether, acetone, and dichloromethane. It has limited solubility in water, consistent with its seven-carbon chain. Compatibility with specific reaction media should be verified experimentally before use in sensitive applications.

How should 2-Methyl-3-hexanol be stored to maintain purity?

Store 2-Methyl-3-hexanol in a tightly sealed container, in a cool and dry location away from oxidizing agents, strong acids, and ignition sources. Confirm exact storage temperature recommendations on the Aladdin Scientific product page or CoA for lot-specific guidance.

What are typical laboratory uses for 2-Methyl-3-hexanol?

Typical uses include its role as a synthetic intermediate or building block in organic chemistry, as an analytical reference standard for GC method development, and as a tool compound in structure–activity relationship studies. It may also appear in solvent studies due to its intermediate hydrophilicity and hydrogen-bonding capacity.

References

1. Royal Society of Chemistry. ChemSpider entry for 2-Methyl-3-hexanol. ChemSpider ID to be confirmed.
2. National Institute of Standards and Technology (NIST). NIST WebBook entry for 2-Methyl-3-hexanol, CAS 617-29-8.
3. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed. Oxford University Press, 2012. General reference for secondary alcohol chemistry and Grignard reactions.
4. Aladdin Scientific. Product page and Safety Data Sheet for 2-Methyl-3-hexanol, SKU M352404.

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