What Is 1-Bromo-4-(trans-4-pentylcyclohexyl)benzene?

1-Bromo-4-(trans-4-pentylcyclohexyl)benzene is an aryl bromide compound in which a bromophenyl group is connected at the para position to a trans-4-pentylcyclohexyl substituent. The trans stereochemistry refers to the diequatorial orientation of the phenyl and pentyl groups on the cyclohexane ring, which imparts a rod-like molecular geometry characteristic of mesogens — the structural units found in liquid crystal materials.

This compound serves as a versatile synthetic building block. The aryl bromide moiety is highly reactive in palladium- and nickel-catalyzed cross-coupling reactions (such as Suzuki–Miyaura, Negishi, and Kumada couplings), enabling researchers to install this cyclohexylphenyl fragment into more complex target molecules. Its rigid, elongated molecular architecture makes it particularly valuable in the design and synthesis of thermotropic liquid crystal compounds and specialty functional materials.

What Are the Key Chemical Properties and Handling Considerations?

The compound has the molecular formula C₁₇H₂₅Br and a molecular weight of approximately 325.29 g/mol (value requires verification against the product specification sheet). The trans isomer is thermodynamically preferred due to the equatorial preference of both large substituents on the cyclohexane ring, conferring greater conformational stability compared with the cis isomer.

As an aryl bromide, 1-Bromo-4-(trans-4-pentylcyclohexyl)benzene should be handled with standard laboratory precautions. Organic bromide compounds may be irritating to skin, eyes, and respiratory tract; use appropriate personal protective equipment including nitrile gloves, safety glasses, and a lab coat. Work in a well-ventilated area or fume hood. Always consult the Safety Data Sheet (SDS) supplied by Aladdin Scientific before use.

The compound is expected to be a solid or low-melting solid at room temperature, consistent with similar cyclohexylbenzene mesogens, but the exact melting point should be confirmed from the product specification. Store in a cool, dry place, protected from light and moisture, and keep the container tightly sealed.

What Reactions and Applications Is This Compound Used For?

Cross-Coupling Chemistry: The aryl C–Br bond undergoes oxidative addition to Pd(0) and Ni(0) catalysts, making this compound an excellent electrophilic partner in Suzuki–Miyaura (with boronic acids/esters), Negishi (with organozinc reagents), Kumada (with Grignard reagents), and Heck reactions. These transformations allow construction of biaryl and aryl-alkene systems incorporating the trans-4-pentylcyclohexyl pharmacophore.

Liquid Crystal Research: The elongated, anisotropic molecular shape of this compound, derived from the coaxially aligned cyclohexane and benzene rings with the trans pentyl chain, is an archetypal mesogenic structural motif. It is employed as an intermediate for synthesizing thermotropic liquid crystal materials used in display technologies, optical films, and electro-optical devices.

Functional Materials: Beyond display applications, derivatives synthesized from this building block may find use in organic semiconductors, self-assembling supramolecular systems, and specialty polymer research where controlled molecular ordering is required.

How Should I Order and What Specifications Are Available?

1-Bromo-4-(trans-4-pentylcyclohexyl)benzene is available from Aladdin Scientific under SKU B186675. To place an order, visit the Aladdin Scientific website, search for the product by name or SKU, select the required quantity and purity grade, and add to cart. Registered academic and institutional customers may be eligible for volume pricing or promotional discounts — contact Aladdin Scientific's sales team for a quotation.

Purity grade and exact available pack sizes should be confirmed on the current product page or by contacting customer service, as specifications may be updated. For large-scale or custom synthesis requirements, inquire about custom order options. When ordering, confirm that the stereochemistry (trans) matches your application requirements, as the cis isomer would have different physical properties and mesogenic behavior.

Storage, Stability, and Quality Assurance

Proper storage of 1-Bromo-4-(trans-4-pentylcyclohexyl)benzene is essential to maintain its chemical integrity. The compound should be stored in a tightly sealed container in a cool, dry environment, away from direct light, heat sources, and moisture. Refrigerated storage (2–8 °C) is generally recommended for aryl bromide compounds to minimize slow decomposition, but confirm the recommended storage temperature from the Aladdin Scientific product label or SDS.

Aladdin Scientific applies rigorous quality control procedures to its reagent catalog. Products are typically characterized by techniques such as GC purity analysis, NMR spectroscopy, and HPLC where appropriate. The purity and specification data are available on the Certificate of Analysis (CoA) supplied with each batch. If you require a CoA for a specific lot number, contact Aladdin Scientific customer service with your order information.

If you observe any changes in the physical appearance of the compound (e.g., discoloration or unusual odor) upon receipt or after storage, contact Aladdin Scientific's technical support team before use. The company's returns and refunds policy covers quality issues — refer to the current policy on the Aladdin Scientific website for details.