426210-81-3

Basic information

• Product Name: 1,1'-Binaphthalene, 2,2'-diethynyl-, (1R)-
• CAS NO: 426210-81-3
• Molecular Formula: C24H14
• Molecular Weight: 302.375
• Mol File: 426210-81-3.mol

Chemical Properties

• CAS DataBase Reference: 1,1'-Binaphthalene, 2,2'-diethynyl-, (1R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-Binaphthalene, 2,2'-diethynyl-, (1R)-(426210-81-3)
• EPA Substance Registry System: 1,1'-Binaphthalene, 2,2'-diethynyl-, (1R)-(426210-81-3)

Safety Data

• Hazardous Substances Data: 426210-81-3(Hazardous Substances Data)

Usage

Chirality

The compound is chiral, meaning it has a non-superimposable mirror image.

Structure

It consists of two naphthalene rings connected by a central ethynyl bridge.

Application in Organic Chemistry

It is used as a chiral ligand in various asymmetric catalytic reactions, particularly in the synthesis of optically pure compounds.

Potential Applications

It has been studied for its potential applications in organic electronics and materials science due to its unique structure and electronic properties.

Building Block

It has shown promise as a building block in the preparation of functionalized materials with potential applications in biomedical and pharmaceutical research.

Stereochemistry

The compound has a specific stereochemistry, denoted by the (1R)prefix, which indicates the configuration of the chiral center.

Optical Purity

It is used in the synthesis of optically pure compounds, which are important in various fields due to their different biological activities.

Electronic Properties

The unique structure of the compound contributes to its electronic properties, making it a potential candidate for applications in organic electronics.

Research Interest

Due to its unique properties and potential applications, 1,1'-Binaphthalene, 2,2'-diethynyl-, (1R)is a subject of interest in various fields of research, including organic chemistry, materials science, and pharmaceutical research.

Upstream product

• 161146-88-9 [1,1′-binaphthalene]-2,2′-dicarboxaldehyde 
• 1034-49-7 (bromomethyl)triphenyl phosphonium bromide 
• 821773-82-4 2,2'-bis[(trimethylsilyl)ethynyl]-1,1'-binaphthalene 
• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 76905-80-1 (S)-2,2'-diiodo-1,1'-binaphthyl 

Downstream Products

• 763109-15-5 2'-ethynyl-2-phenylethynyl-[1,1']binaphthalenyl 
• 763109-14-4 trimethyl-(2'-phenylethynyl-[1,1']binaphthalenyl-2-ylethynyl)-silane 
• 763109-17-7 2-(3-ethynyl-phenylethynyl)-2'-phenylethynyl-[1,1']binaphthalenyl 
• 763109-16-6 trimethyl-[3-(2'-phenylethynyl-[1,1']binaphthalenyl-2-ylethynyl)-phenylethynyl]-silane 
• 426210-89-1 [2'-(3-iodo-phenylethynyl)-[1,1']binaphthalenyl-2-ylethynyl]-trimethyl-silane 
• 426210-91-5 [2'-(3-iodo-5-nitro-phenylethynyl)-[1,1']binaphthalenyl-2-ylethynyl]-trimethyl-silane 

Relevant articles and documents

Chiral binaphthalenes bearing two pyridine ligands attached via acetylene spacers. Synthesis and coordination study

An effective methodology has been developed for the synthesis of enantiopure 2,2′-dialkynylated 1,1′-binaphthalene derivatives. Enantiopure 2,2′-diiodo-1,1′-binaphthalene (10) provided 2,2′-diethynyl-1,1′-binaphthalene (16) in the Negishi alkynylation sup

Easily oxidizable triarylamine materials with naphthalene and binaphthalene core: structure–properties relationship

We devised and synthesized a series of electron-rich compounds featuring diphenylamine, carbazole or dibenzo[c,g]carbazole connected via phenylacetylene linkers to an aromatic central unit. The key synthetic step was a high yielding cross coupling reaction between halogenated (bi)naphthalene and organometallic reagents prepared in situ from terminal alkynes (side-arms). By masking one of the iodo functions with a diethyltriazenyl group in the side-arm precursors, we efficiently circumvented the formation of doubly aminated by-products. Although one step longer, this approach led to higher yields of terminal alkynes than the direct coupling route. Spectroscopic and electrochemical measurements supported by computational evidence revealed that conjugation in the 1,4-disubstituted naphthalene backbone is superior to the 1,5 or 2,6 substituted cores. The diphenylamine derivative gets oxidized more readily when compared to its carbazole analogs. Expanding the core to binaphthalene did not alter electronic properties, but influenced the physical characteristics significantly.

Design and synthesis of the first triply twisted Moebius annulene

As long as 50 years ago theoretical calculations predicted that Moebius annulenes with only one π surface and one edge would exhibit peculiar electronic properties and violate the Hueckel rules. Numerous synthetic attempts notwithstanding, the first singly twisted Moebius annulene was not prepared until 2003. Here we present a general, rational strategy to synthesize triply or even more highly twisted cyclic π systems. We apply this strategy to the preparation of a triply twisted [24]dehydroannulene, the structure of which was confirmed by X-ray analysis. Our strategy is based on the topological transformation of 'twist' into 'writhe'. The advantage is twofold: the product exhibits a lower degree of strain and precursors can be designed that inherently include the writhe, which, after cyclization, ends up in the Moebius product. With our strategy, triply twisted systems are easier to prepare than their singly twisted counterparts.

Enantiopure double-helical alkynyl cyclophanes

The "commercially available chirality" of the binaphthyl units and the efficiency of the coupling reactions were crucial to the synthesis of double-helical alkynyl cylophanes 1 in enantiopure form. The unique properties of these molecules have been unambi