1-Bromooctadecane
[CAS# 112-89-0]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 1-Bromooctadecane
• Synonyms: n-Octadecyl bromide; Stearyl bromide
• Molecular Formula: C₁₈H₃₇Br
• Molecular Weight: 333.39
• CAS Registry Number: 112-89-0
• EC Number: 204-013-4
• SMILES: CCCCCCCCCCCCCCCCCCBr

Properties

• Density: 0.976
• Melting point: 20-23 °C
• Boiling point: 214-216 °C (12 mmHg)
• Refractive index: 1.462-1.464
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

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

Discovery and Applications

1-Bromooctadecane is an organic compound with the chemical formula C18H37Br, consisting of a long carbon chain of eighteen atoms with a bromine atom attached to one end. This compound belongs to the class of alkyl halides and is commonly used as a versatile reagent in organic synthesis. Its structure, characterized by the long hydrophobic alkyl chain, makes it valuable in applications ranging from surface chemistry to the synthesis of complex molecules.

The discovery and use of 1-bromooctadecane can be traced back to the growing interest in organohalides during the late 19th and early 20th centuries. Organic halides became essential building blocks in organic synthesis due to their reactivity, particularly in nucleophilic substitution reactions. 1-Bromooctadecane, specifically, can be synthesized via the bromination of octadecanol (stearyl alcohol) using a brominating agent such as phosphorus tribromide or hydrobromic acid. This process yields a product that is reactive due to the presence of the bromine atom, which can be easily replaced in subsequent reactions.

One of the key applications of 1-bromooctadecane is in the field of surface chemistry. The long hydrophobic chain allows the compound to be used in forming self-assembled monolayers (SAMs) on surfaces such as gold. These monolayers are critical in studying surface properties, catalysis, and the development of nanoscale devices. The ability of 1-bromooctadecane to align itself in an orderly manner on surfaces due to the hydrophobic interactions of the alkyl chains makes it ideal for creating stable, uniform coatings.

In organic synthesis, 1-bromooctadecane is employed as an alkylating agent. Its bromine atom can be substituted by various nucleophiles, facilitating the introduction of a long alkyl chain into more complex molecules. This makes the compound useful in the synthesis of surfactants, detergents, and other molecules that require hydrophobic tails. Additionally, it is used in the production of quaternary ammonium salts, which find applications in antimicrobial agents, fabric softeners, and phase-transfer catalysts.

The long alkyl chain of 1-bromooctadecane also renders it useful in lipid research and the development of lipophilic materials. The compound can be incorporated into the structure of lipid-like molecules, influencing properties such as solubility, membrane fluidity, and surface interactions. Its role in lipid chemistry has made it valuable in the development of materials for drug delivery and bioactive compounds.

In industrial chemistry, 1-bromooctadecane is also utilized in the production of waxes, lubricants, and other products that benefit from the hydrophobic nature of the long alkyl chain. These applications leverage the compound’s physical properties, particularly its ability to form smooth, non-polar surfaces that repel water and reduce friction.

Safety considerations when handling 1-bromooctadecane include its potential to cause irritation to the skin, eyes, and respiratory system. As an alkyl halide, it can also be harmful if ingested or inhaled in large quantities, necessitating appropriate safety precautions during use.

In conclusion, 1-bromooctadecane has become an important reagent in organic chemistry, surface science, and industrial applications. Its reactivity and long hydrophobic chain make it a valuable compound for forming monolayers, synthesizing surfactants, and developing lipophilic materials.

References

2019. Synthesis and characterization of new quaternary ammonium surfactant [C18-Dabco][Br] and its catalytic application in the synthesis of spirocarbocycles under ultrasonic condition. Research on Chemical Intermediates.
DOI: 10.1007/s11164-018-3690-8

2023. Synthesis of covalent organic pillars as molecular nanotubes with precise length, diameter and chirality. Nature Synthesis.
DOI: 10.1038/s44160-022-00235-w

2024. Synthesis and characterization of ester-free poly(trimethylene carbonate) bearing long-alkyl moieties and its degradation. Polymer Journal.
DOI: 10.1038/s41428-024-00984-9