1-Chlorohexane: Properties, Uses & Lab Guide

1-Chlorohexane is a straight-chain primary alkyl chloride widely used as a versatile alkylating agent and intermediate in organic synthesis research.

Chemical Formula

C6H13Cl

Molecular Weight

120.62 g/mol

CAS Number

544-10-5

Appearance

Colorless to pale yellow liquid

Boiling Point

135 °C (literature)

Density

0.879 g/mL at 25 °C (literature)

SKU

C109280

Chemical Identity and Physical Properties

1-Chlorohexane (systematic IUPAC name: 1-chlorohexane; CAS 544-10-5) is a primary alkyl halide with the molecular formula C₆H₁₃Cl and a molecular weight of 120.62 g/mol. It presents as a colorless to pale yellow, mobile liquid at room temperature with a mild, characteristic hydrocarbon odor. Key physical constants reported in the literature include a boiling point of approximately 135 °C and a density of approximately 0.879 g/mL at 25 °C. The compound is practically insoluble in water but freely miscible with common organic solvents such as diethyl ether, dichloromethane, tetrahydrofuran, and hydrocarbons. Its relatively high boiling point compared to shorter-chain alkyl chlorides reflects the increased van der Waals interactions along the six-carbon chain, making it easier to handle under standard laboratory conditions without excessive volatility losses.

Synthetic Applications in Organic Chemistry

1-Chlorohexane serves as a fundamental building block and electrophilic alkylating agent across a broad range of synthetic transformations. Its primary alkyl structure makes it highly reactive toward S_N2 nucleophilic substitution, enabling efficient introduction of the hexyl chain into target molecules. Key applications include:

• Grignard Reagent Preparation: Reaction with magnesium turnings in anhydrous diethyl ether or THF affords hexylmagnesium chloride, a versatile nucleophile for carbon–carbon bond formation with aldehydes, ketones, esters, and epoxides.
• Organolithium Chemistry: Treatment with n-butyllithium or lithium metal can furnish hexyllithium, useful in highly reactive additions.
• Alkylation of Heteroatom Nucleophiles: 1-Chlorohexane is routinely used to N-alkylate amines, O-alkylate alcohols and phenols, and S-alkylate thiols under basic conditions, providing hexyl ethers, thioethers, and tertiary amines.
• Williamson Ether Synthesis: Reaction with sodium or potassium alkoxides allows straightforward access to hexyl ethers employed as model substrates in physical organic studies.
• Phase-Transfer and Surfactant Research: The hexyl chain length is frequently employed in studies of amphiphilic molecules, lipid mimics, and self-assembling systems.

The primary carbon bearing chlorine ensures minimal competing elimination under mild conditions, offering excellent selectivity in S_N2-driven reactions.

Safe Handling, Storage, and Regulatory Information

1-Chlorohexane is a flammable liquid and must be handled with appropriate precautions. The following safety guidelines reflect standard practice for primary alkyl chlorides of this carbon chain length:

• Flammability: The compound has a flash point in the range typically associated with flammable liquids (exact value should be confirmed on the current SDS). Keep away from open flames, sparks, and hot surfaces. Use explosion-proof electrical equipment in storage areas.
• Ventilation: Work in a well-ventilated fume hood. Vapors are heavier than air and may accumulate at floor level.
• Personal Protective Equipment (PPE): Wear chemical-resistant gloves (e.g., nitrile or neoprene), safety glasses or goggles, and a lab coat. For prolonged or high-concentration exposure, use a respirator equipped with an organic vapor cartridge.
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area away from oxidizing agents, strong bases, and ignition sources. Recommended storage temperature is typically 2–30 °C; confirm on product label.
• Waste Disposal: Dispose of as halogenated organic waste in accordance with local, regional, and national environmental regulations.
• First Aid: In case of skin or eye contact, flush thoroughly with water. If inhaled, remove to fresh air. Seek medical attention as needed.

Researchers should always consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific before use, as it contains the most up-to-date hazard classification, GHS pictograms, and regulatory data.

Quality Specifications and Ordering Information

Aladdin Scientific supplies 1-Chlorohexane (SKU: C109280) suitable for research and general laboratory use. Researchers and procurement teams should consider the following when ordering:

• Purity: Check the current certificate of analysis (CoA) for lot-specific purity data. Typical specifications for research-grade primary alkyl chlorides include purity assessed by GC.
• Packaging: Available in multiple pack sizes to support discovery-scale experiments through larger preparative work. Contact Aladdin Scientific for custom quantities.
• Lot Traceability: Each lot ships with a CoA; lot numbers are referenced for reproducibility in publications.
• Shelf Life and Re-testing: Store under recommended conditions. Re-test if the material has been stored beyond the stated shelf life or if color changes are observed, as traces of HCl can develop over time due to slow hydrolysis or oxidation.
• Technical Support: Aladdin Scientific technical specialists are available to assist with product selection, specification questions, and application guidance.

Frequently asked questions

What is 1-Chlorohexane used for in organic synthesis?

1-Chlorohexane is primarily used as an electrophilic alkylating agent to introduce a hexyl chain via SN2 reactions. Common applications include preparation of hexylmagnesium chloride (Grignard reagent), Williamson ether synthesis, N- and O-alkylation of nucleophiles, and as a building block in surfactant and lipid-mimetic research.

How should 1-Chlorohexane be stored to maintain stability?

Store 1-Chlorohexane in a tightly sealed container at 2–30 °C in a cool, dry, well-ventilated area away from heat sources, oxidizing agents, and strong bases. Because alkyl chlorides can slowly generate HCl upon hydrolysis or extended storage, monitor for color changes and re-test purity if the material has been stored beyond its stated shelf life.

Is 1-Chlorohexane a primary, secondary, or tertiary alkyl halide?

1-Chlorohexane is a primary alkyl halide, as the chlorine atom is attached to the terminal (C-1) carbon of the hexane chain. This primary structure makes it highly reactive in SN2 substitution reactions and minimizes competing E2 elimination under mild base conditions.

What personal protective equipment (PPE) is recommended when handling 1-Chlorohexane?

Use chemical-resistant gloves (nitrile or neoprene), safety glasses or splash goggles, and a laboratory coat. Conduct all manipulations in a properly functioning fume hood. For operations involving larger quantities or prolonged exposure, an organic vapor respirator cartridge is recommended. Always consult the current SDS for complete hazard information.

Can 1-Chlorohexane be used directly to prepare a Grignard reagent?

Yes. 1-Chlorohexane reacts with magnesium turnings in anhydrous THF or diethyl ether under inert atmosphere (nitrogen or argon) to form hexylmagnesium chloride. Strict exclusion of moisture and oxygen is essential for successful Grignard formation and to prevent premature quenching of the reagent.

References

1. March, J.; Smith, M. B. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th ed.; Wiley: Hoboken, NJ, 2013.
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012.
3. National Institute of Standards and Technology (NIST). 1-Chlorohexane. NIST WebBook, SRD 69. https://webbook.nist.gov/

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