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

General Description

1,13-dibromotricyclo (8,2,2,2 4.7)-hexadeca-4,6,10,12,13,15-hexane is a complex organic compound with a unique tricyclic structure. It contains three cyclohexane rings, with bromine atoms attached at the 1 and 13 positions. The molecular formula C16H18Br2 indicates that it consists of 16 carbon atoms and 18 hydrogen atoms. 1,13-dibromotricyclo (8,2,2,2 4.7)-hexadeca-4,6,10,12,13,15-hexane is primarily used in organic synthesis and research applications due to its complex and specific structure. It may have potential uses as a building block for novel chemical compounds or as a reagent in diverse chemical reactions. Additionally, its complex structure may also lend itself to the study of organic chemistry and molecular structure.

Upstream product

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

Downstream Products

• 1186137-51-8 4-benzhydrylideneamino-15-bromo[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 
• 5628-20-6 4-bromo-15-hydroxy[2.2]paracyclophane 
• 162103-17-5 4,15-bis(4-tolyl)-<2.2>paracyclophane 
• 162103-20-0 4,15-bis(4-methoxyphenyl)-<2.2>paracyclophane 
• 124618-53-7 pseudo-m-dibenzoyl<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.