6-Chlorohexanol
[CAS# 2009-83-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty alcohol
• Name: 6-Chlorohexanol
• Synonyms: 1-Chloro-6-hydroxyhexane; 6-Chloro-1-hexanol; Hexamethylene chlorohydrin
• Molecular Formula: C₆H₁₃ClO
• Molecular Weight: 136.62
• CAS Registry Number: 2009-83-8
• EC Number: 217-925-2
• SMILES: C(CCCCl)CCO

Properties

• Density: 1.024
• Boiling point: 108-112 °C (14 mmHg)
• Refractive index: 1.4547-1.4567
• Flash point: 98 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H312-H315-H319-H332
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P317-P321-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 2810

Discovery and Applications

6-Chlorohexanol is a notable organic compound with the molecular formula C6H13ClO. It is a chlorinated alcohol that has found applications in various industrial and chemical processes. The discovery and synthesis of 6-Chlorohexanol have contributed significantly to its diverse applications, particularly in the fields of organic synthesis and pharmaceuticals.

The discovery of 6-Chlorohexanol emerged from research focused on halogenated alcohols and their potential utility in chemical synthesis. The compound is typically synthesized through the chlorination of hexanol, which introduces a chlorine atom at the sixth carbon position of the hexyl chain. This process is usually carried out using chlorine gas or chlorinating agents under controlled conditions to ensure high yield and purity of the chlorinated product.

In organic synthesis, 6-Chlorohexanol is used as a key intermediate in the preparation of various chemical derivatives. Its chlorinated structure makes it a valuable reagent for nucleophilic substitution reactions, where the chlorine atom can be replaced by different nucleophiles to form a range of products. This property is exploited in the synthesis of complex molecules and functionalized compounds, which are important in the development of new materials and chemicals.

Pharmaceutical applications of 6-Chlorohexanol are also notable. The compound serves as a building block in the synthesis of various drug molecules and bioactive compounds. Its ability to act as an intermediate in the formation of other chemical entities makes it useful in drug discovery and development. The incorporation of the chlorohexanol moiety into pharmaceutical compounds can enhance their biological activity or modify their pharmacokinetic properties.

In addition to its use in pharmaceuticals, 6-Chlorohexanol finds applications in the production of surfactants and polymer additives. The compound's chemical properties make it suitable for modifying the properties of polymers and surfactants, contributing to the development of new materials with specific functional characteristics. It is also employed in the manufacture of specialty chemicals and industrial products, where its chlorinated structure provides unique reactivity and stability.

Overall, 6-Chlorohexanol is an important compound in the field of organic chemistry due to its versatile applications. Its role as an intermediate in chemical synthesis, its utility in pharmaceuticals, and its applications in materials science highlight its significance in various industrial and research contexts.

References

2024. Synthetic peptide branched polymers for antibacterial and biomedical applications. *Nature Reviews Bioengineering*.
DOI: 10.1038/s44222-023-00143-4

2021. An acid-triggered porphyrin-based block copolymer for enhanced photodynamic antibacterial efficacy. *Science China Chemistry*.
DOI: 10.1007/s11426-020-9904-7

2019. A Novel Natural Dye Derivative for Natural Fabric Supercritical Carbon Dioxide Dyeing Technology. *Fibers and Polymers*.
DOI: 10.1007/s12221-019-9029-2

2018. Synthesis and Properties of Hydroxyl-Containing Ionic Liquids. *Russian Journal of Organic Chemistry*.
DOI: 10.1134/s1070428018010153

2017. Reversible change of wettability in poly(ɛ-caprolactone/azobenzene) honeycomb-patterned films by UV and visible light illumination. *Polymer Bulletin*.
DOI: 10.1007/s00289-017-1948-8