1,4-Dibromocyclohexane

• CAS: 35076-92-7
• Catalog Number: ACM35076927
• Category: Main Products
• Molecular Weight: 241.95
• Molecular Formula: C₆H₁₀Br₂
• Synonyms: 1,4-dibromo-cyclohexan;1,4-DIBROMOCYCLOHEXANE;1 4-DIBROMOCYCLOHEXANE TECH
• IUPAC Name: 1,4-dibromocyclohexane
• SMILES: C1CC(CCC1Br)Br
• InChI Key: OALGWDQLKYPDRK-UHFFFAOYSA-N
• Boiling Point: 224.9ºC at 760mmHg
• Flash Point: 95.1ºC
• Density: 1.789g/cm³
• EC Number: 252-349-5
• Exact Mass: 239.91500

Case Study

Application of 1,4-Dibromocyclohexane as a Critical Spacer in Antitumor Cyanine Dye Synthesis

El-Mekawy, Rasha E., et al. Bioorganic & Medicinal Chemistry Letters 28.10 (2018): 1747-1752.

Bifunctional alkyl halides that reliably install spacer units are valuable in the synthesis of multi-charged chromophores and related organic materials. 1,4-Dibromocyclohexane serves as a symmetric, di-electrophilic linker that enables straightforward construction of bis-quaternary pyridinium intermediates used to access a family of dimethine, bis-dimethine and longer cyanine dyes.
In this work, 1,4-dibromocyclohexane was reacted with benzylpyridine to generate the key bis-pyridinium salt (1) - a central synthon that subsequently underwent condensation and coupling sequences to furnish a series of cyanine dyes tested for antitumor activity. The cyclohexyl dibromide thus functions as a spacer/bridge that couples two heterocyclic termini while imparting a defined three-dimensional separation between chromophoric units.
Synthesis of bis-pyridinium salt (1): Two equivalents of benzylpyridine were heated with the appropriate stoichiometry of 1,4-dibromocyclohexane in refluxing xylene to effect bis-alkylation. After workup and chromatographic purification, the bis-pyridinium dibromide salt was isolated in high yield (reported ~85%). The crude product was purified by column chromatography (eluent ethyl acetate : methanol 95:5).
This bis-pyridinium salt served as the fundamental building block for subsequent chemistry. It was successfully employed in reactions with various aldehydes to produce a series of cyanine dyes. Biological evaluation revealed that several of these compounds exhibited significant antitumor activity against various cancer cell lines, including liver (HepG2), cervical (Hela), and breast (MCF-7) cancers.

Custom Q&A

What is the molecular formula of 1,4-Dibromocyclohexane?

The molecular formula of 1,4-Dibromocyclohexane is C6H10Br2.

What are the synonyms of 1,4-Dibromocyclohexane?

The synonyms of 1,4-Dibromocyclohexane are 1,4-DIBROMOCYCLOHEXANE, 35076-92-7, 13618-83-2, Cyclohexane, 1,4-dibromo-, TRANS-1,4-DIBROMOCYCLOHEXANE, 1beta,4alpha-Dibromocyclohexane, and more.

What is the IUPAC name of 1,4-Dibromocyclohexane?

The IUPAC name of 1,4-Dibromocyclohexane is 1,4-dibromocyclohexane.

What is the InChI of 1,4-Dibromocyclohexane?

The InChI of 1,4-Dibromocyclohexane is InChI=1S/C6H10Br2/c7-5-1-2-6(8)4-3-5/h5-6H,1-4H2.

What is the InChIKey of 1,4-Dibromocyclohexane?

The InChIKey of 1,4-Dibromocyclohexane is OALGWDQLKYPDRK-UHFFFAOYSA-N.

What is the canonical SMILES of 1,4-Dibromocyclohexane?

The canonical SMILES of 1,4-Dibromocyclohexane is C1CC(CCC1Br)Br.

What is the CAS number of 1,4-Dibromocyclohexane?

The CAS number of 1,4-Dibromocyclohexane is 35076-92-7.

What is the molecular weight of 1,4-Dibromocyclohexane?

The molecular weight of 1,4-Dibromocyclohexane is 241.95g/mol.

What is the XLogP3 value of 1,4-Dibromocyclohexane?

The XLogP3 value of 1,4-Dibromocyclohexane is 3.1.

What is the Covalently-Bonded Unit Count of 1,4-Dibromocyclohexane?

The Covalently-Bonded Unit Count of 1,4-Dibromocyclohexane is 1.