136984-20-8

Basic information

• Product Name: 1,13-dibromotricyclo (8,2,2,2 4.7)-hexadeca-4,6,10,12,13,15-hexane
• Synonyms: 1,13-dibromotricyclo (8,2,2,2 4.7)-hexadeca-4,6,10,12,13,15-hexane
• CAS NO: 136984-20-8
• Molecular Formula: C₁₆H₁₄Br₂
• Molecular Weight: 366.09
• Mol File: 136984-20-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 417.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.565±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,13-dibromotricyclo (8,2,2,2 4.7)-hexadeca-4,6,10,12,13,15-hexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,13-dibromotricyclo (8,2,2,2 4.7)-hexadeca-4,6,10,12,13,15-hexane(136984-20-8)
• EPA Substance Registry System: 1,13-dibromotricyclo (8,2,2,2 4.7)-hexadeca-4,6,10,12,13,15-hexane(136984-20-8)

Safety Data

• Hazardous Substances Data: 136984-20-8(Hazardous Substances Data)

Usage

Description

1,13-dibromotricyclo (8,2,2,2 4.7)-hexadeca-4,6,10,12,13,15-hexane is a complex organic compound characterized by its unique tricyclic structure. It features three cyclohexane rings with bromine atoms attached at the 1 and 13 positions. The molecular formula C16H18Br2 signifies that it is composed of 16 carbon atoms and 18 hydrogen atoms, along with two bromine atoms. 1,13-dibromotricyclo (8,2,2,2 4.7)-hexadeca-4,6,10,12,13,15-hexane is known for its specific structure, which makes it valuable in organic synthesis and research applications.

Uses

Used in Organic Synthesis:
1,13-dibromotricyclo (8,2,2,2 4.7)-hexadeca-4,6,10,12,13,15-hexane is used as a building block in the synthesis of novel chemical compounds due to its complex and specific structure. Its unique arrangement of atoms and rings allows for the creation of new molecules with potential applications in various fields.
Used in Research Applications:
In the field of research, 1,13-dibromotricyclo (8,2,2,2 4.7)-hexadeca-4,6,10,12,13,15-hexane serves as a valuable compound for studying organic chemistry and molecular structure. Its intricate arrangement of atoms and rings provides researchers with an opportunity to explore new reaction pathways and mechanisms, contributing to the advancement of chemical knowledge.
Used in Chemical Reactions:
As a reagent, 1,13-dibromotricyclo (8,2,2,2 4.7)-hexadeca-4,6,10,12,13,15-hexane is utilized in diverse chemical reactions. Its unique structure allows it to participate in various types of reactions, such as substitution, addition, or elimination, enabling the synthesis of a wide range of products with different properties and applications.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, the complex structure of 1,13-dibromotricyclo (8,2,2,2 4.7)-hexadeca-4,6,10,12,13,15-hexane may also have potential applications in the pharmaceutical industry. Its unique molecular architecture could be harnessed for the development of new drugs or drug delivery systems, targeting specific biological pathways or receptors.

Upstream product

• 1633-22-3 [2.2]Paracyclophan 
• 19900-52-8 1,4-bisbromomethyl-2-bromobenzene 

Downstream Products

• 124618-53-7 pseudo-m-dibenzoyl<2.2>paracyclophane 
• 162103-20-0 4,15-bis(4-methoxyphenyl)-<2.2>paracyclophane 
• 162103-17-5 4,15-bis(4-tolyl)-<2.2>paracyclophane 
• 5628-20-6 4-bromo-15-hydroxy[2.2]paracyclophane 
• 107496-62-8 [1-[13-(Hydrazono-phenyl-methyl)-tricyclo[8.2.2.2^4,7]hexadeca-1⁽¹³⁾,4⁽¹⁶⁾,5,7⁽¹⁵⁾,10⁽¹⁴⁾,11-hexaen-5-yl]-1-phenyl-meth-(Z)-ylidene]-hydrazine 
• 1186137-51-8 4-benzhydrylideneamino-15-bromo[2.2]paracyclophane 

Relevant articles and documents

Regioselective Synthesis of 4,7,12,15-Tetrasubstituted [2.2]Paracyclophanes: A Modular Route Involving Optical Resolution

A practical synthetic method for preparing bis-(para)-pseudo-ortho and bis-(para)-pseudo-meta type 4,7,12,15-tetrasubstituted [2.2]paracyclophanes is reported. Regioselective double Rieche formylation was successfully applied to the corresponding dibromo[2.2]paracyclophanes under slightly modified conditions. Aldehydes reacted in an unknown direction with Rieche formylation agents, dichloromethyl methyl ether and titanium(IV) tetrachloride, leading to the formation of benzal chlorides. Formylated products were obtained after hydrolysis of these benzal chloride derivatives. Optical resolution was performed with the diastereomer method and (RP)-4,12-dibromo-7,15-diformyl[2.2]paracyclophane was successfully obtained in an enantiomerically pure form (99 % ee). Their synthetic utility is demonstrated with some exploratory transformations to access corresponding differently functionalized tetrasubstituted [2.2]paracyclophane derivatives.

Synthesis, chiral resolution, and absolute configuration of dissymmetric 4,15-difunctionalized [2.2]paracyclophanes

Despite the fact that functionalized planar chiral [2.2]paracyclophanes have received a lot of attention, the chemistry of pseudo-meta 4,15-distubstituted [2.2]paracyclophanes is largely unexplored. This is mainly due to the fact that the 4,5-dibromo-functionalized [2.2]paracyclophane is much less prone to halogen-metal exchange reactions than its constitutional pseudo-ortho or pseudo-para isomers. Here, we give an account of an efficient protocol to achieve this, which allows the synthesis of a broad variety of 4,15-disubstituted [2.2]paracyclophanes. Furthermore, we were able to resolve several of the racemic compounds via chiral HPLC and assign the absolute configurations of the isolated enantiomers by X-ray diffraction and/or by the comparison of calculated and measured CD-spectra.

Cyclophanes. Part LII: Ethynyl[2.2]paracyclophanes - New building blocks for molecular scaffolding

The synthesis of seven ethynyl[2.2]paracyclophanes is described. The five diethynyl derivatives 4,5-diethynyl[2.2]paracyclophane (12), pseudo-gem-(13), pseudo-ortho-(14), pseudo-meta-(15), and pseudo-para-diethynyl[2.2] paracyclophane (16), the tetraethynyl compound 4,7,13,16-tetraethynyl[2.2] paracyclophane (17), and for comparison the mono-ethynylated hydrocarbon 4-ethynyl[2.2]paracyclophane (11) have been prepared. The structures of these new building blocks for carbon rich systems were determined by the usual analytical and spectroscopic methods.