7-Bromo-1-heptanol
[CAS# 10160-24-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Halogenated aliphatic hydrocarbon
• Name: 7-Bromo-1-heptanol
• Molecular Formula: C₇H₁₅BrO
• Molecular Weight: 195.10
• CAS Registry Number: 10160-24-4
• EC Number: 628-171-2
• SMILES: C(CCCO)CCCBr

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*, 1.269 g/mL (Expl.)
• Boiling point: 231.8±23.0 °C 760 mmHg (Calc.)^*, 298.5 - 300 °C (Expl.)
• Flash point: 98.6±12.3 °C (Calc.)^*, 113 °C (Expl.)
• Index of refraction: 1.477 (Calc.)^*, 1.482 (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovery and Applications

7-Bromo-1-heptanol is an organic compound that belongs to the family of bifunctional aliphatic alcohols containing a halogen substituent. Its molecular formula is C₇H₁₅BrO, and the structure consists of a seven-carbon linear chain bearing a hydroxyl group at carbon 1 and a bromine atom at carbon 7. This spatial separation between the two functional groups makes 7-bromo-1-heptanol a versatile intermediate in synthetic organic chemistry, particularly in the preparation of macrocyclic compounds, surfactants, and polymer building blocks.

The compound was developed and characterized during research into ω-bromoalkanols, a class of compounds important in nucleophilic substitution reactions and in the synthesis of heterocycles. The most common route of synthesis for 7-bromo-1-heptanol involves the opening of oxiranes or terminal epoxides by hydrogen bromide in the presence of alcohols, or more directly through partial bromination of 1,7-heptanediol using phosphorus tribromide or other selective halogenating agents. The compound can also be obtained by the hydrolysis of the corresponding ω-bromoheptyl acetate, followed by purification through distillation or recrystallization.

The unique reactivity of 7-bromo-1-heptanol lies in the dual presence of a primary alcohol and a terminal alkyl bromide. The hydroxyl group can undergo standard transformations such as esterification, etherification, or oxidation, while the bromine atom is readily displaced in nucleophilic substitution reactions. This allows the compound to serve as a synthetic handle for introducing a wide range of functionalities, including amines, thiols, and azides. These reactions make it useful in the construction of spacers, linkers, or precursors to macrocyclic systems via intramolecular cyclization.

One of the well-documented applications of 7-bromo-1-heptanol is in the synthesis of seven-membered or larger ring compounds, including lactones, lactams, and crown ethers. The compound can be cyclized under basic or acidic conditions to form oxacycloheptane derivatives or converted into azepane rings by intramolecular displacement with a nitrogen nucleophile. These transformations are of interest in the development of host–guest chemistry and materials science, where such macrocycles are used to complex metal ions or small organic molecules.

In materials chemistry, 7-bromo-1-heptanol is employed in the functionalization of surfaces and polymers. The alkyl chain provides hydrophobic character, while the reactive termini allow for covalent attachment to diverse substrates. It has been utilized in the preparation of surface-active agents, often through further derivatization into quaternary ammonium salts or esterified surfactants. These derivatives can modulate the wetting properties, emulsification, or dispersibility of formulations in coatings, textiles, or personal care products.

Although the compound itself is not known for pharmacological activity, its derivatives have been studied in medicinal chemistry as part of linker groups or side chains in drug candidates. The long alkyl chain contributes to membrane permeability, and the terminal hydroxyl group enhances solubility or hydrogen bonding interactions. In bioconjugation chemistry, 7-bromo-1-heptanol has been explored as a spacer for attaching bioactive molecules to polymers or solid supports.

From a physical and chemical standpoint, 7-bromo-1-heptanol is a colorless to pale yellow liquid at room temperature, with low solubility in water but good solubility in most organic solvents. It has a relatively high boiling point due to the presence of both polar and nonpolar functional groups. The bromine atom increases the molecular weight and contributes to higher refractive index and density compared to the corresponding non-halogenated alcohol.

The stability of 7-bromo-1-heptanol under ambient conditions is moderate. It is sensitive to light and heat, which can promote elimination or decomposition reactions, and should be stored under an inert atmosphere. Handling requires standard precautions to avoid prolonged exposure, as alkyl bromides may act as alkylating agents and irritants.

As a representative member of the ω-bromoalkanol series, 7-bromo-1-heptanol is well-documented in the literature and continues to be employed in the synthesis of cyclic, polymeric, and surface-active compounds, demonstrating its value as a bifunctional chemical intermediate in both academic and industrial contexts.

References

2022. Nickel-Catalyzed Asymmetric Reductive Ring Opening of Cyclobutanones with Alkyl Bromides. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-238-00218