109744-41-4

Basic information

• Product Name: 1-iodo-2-(2-phenylethynyl)benzene
• Synonyms: 1-iodo-2-(2-phenylethynyl)benzene
• CAS NO: 109744-41-4
• Molecular Weight: 304.13
• Mol File: 109744-41-4.mol
• Article Data: 28

Chemical Properties

• Melting Point: 62-65 °C
• Boiling Point: 160-162 °C
• Density: 1.63±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1-iodo-2-(2-phenylethynyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-iodo-2-(2-phenylethynyl)benzene(109744-41-4)
• EPA Substance Registry System: 1-iodo-2-(2-phenylethynyl)benzene(109744-41-4)

Safety Data

• Hazardous Substances Data: 109744-41-4(Hazardous Substances Data)

Usage

Derivative of benzene

This compound is derived from benzene, a basic aromatic hydrocarbon structure, and contains additional functional groups.

Iodine atom

The presence of an iodine atom in the molecular structure contributes to the compound's unique reactivity and properties.

Phenylethynyl group

The phenylethynyl group, which is an ethynyl (acetylenic) group attached to a phenyl ring, is another functional group in this compound.

Organic synthesis building block

1-iodo-2-(2-phenylethynyl)benzene is commonly used as a building block in organic synthesis, allowing for the creation of more complex organic molecules.

Precursors for other organic compounds

This compound can act as a useful precursor for the preparation of various other organic compounds, making it valuable in chemical research.

Industries usage

Pharmaceutical and agrochemical
The compound is mainly used in the pharmaceutical and agrochemical industries as an intermediate for the synthesis of other organic compounds.

Unique reactivity

The combination of the iodine atom and the phenylethynyl group gives 1-iodo-2-(2-phenylethynyl)benzene unique reactivity, which is beneficial in organic chemistry research and experimentation.

Upstream product

• 100-44-7 benzyl chloride 
• 4706-43-8 1-benzyl-1H-benzotriazole 
• 26260-02-6 2-iodobenzaldehyde 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 536-74-3 phenylacetylene 
• 119-61-9 benzophenone 
• 19997-66-1 1-iodo-2,2-diphenylethylene 
• 583-55-1 1-Bromo-2-iodobenzene 
• 615-43-0 2-iodophenylamine 
• 615-42-9 1,2-Diiodobenzene 
• 100-39-0 benzyl bromide 
• 3112-88-7 Benzyl phenyl sulfone 
• 21375-88-2 1-bromo-2-(phenylethenyl)benzene 
• 13141-38-3 2-phenylethynylaniline 

Downstream Products

• 727975-12-4 3-(2-(2-phenylethynyl)phenyl)prop-2-yn-1-ol 
• 1558817-99-4 C₂₃H₁₈O₂ 
• 1558818-04-4 C₂₅H₂₂O₂ 
• 13203-60-6 1,2-bis(2-phenylethynyl)benzene 
• 1220993-87-2 2'-(phenylethynyl)-[1,1'-biphenyl]-4-carbonitrile 
• 1021176-06-6 2-(phenylethynyl)-4'-(trifluoromethyl)-1,1'-biphenyl 

Relevant articles and documents

Chemical synthesis of hormone receptor probes: High affinity photoactivated enediyne-estrogens

A family of enediyne-estrogens has been prepared, and evaluated for affinity to hER. The optimal ligand has nM affinity, and undergoes photoBergman cycloaromatization.

Simple and efficient diaryl alkyne synthesis method

The embodiment of the invention discloses a simple and efficient diaryl alkyne synthesis method. The method comprises the steps of by taking arylmethylbenzotriazole and aromatic aldehyde as raw materials, carrying out addition and double-beta-elimination reaction under the action of bis (trimethylsilyl) amino salt MN (SiMe3) 2 to synthesize diaryl alkyne by a one-pot method. The raw materials and chemical reagents used in the method are easy to obtain, the reaction conditions are mild, the operation is simple, the substrate universality is good, the product yield is high, and the method is a simple and efficient diaryl alkyne synthesis method.

Enantioselective Rh(II)-Catalyzed Desymmetric Cycloisomerization of Diynes: Constructing Furan-Fused Dihydropiperidines with an Alkyne-Substituted Aza-Quaternary Stereocenter

Described herein is an enantioselective dirhodium(II)-catalyzed cycloisomerization of diynes achieved by the strategy of desymmetrization, which not only represents a new cycloisomerization reaction of diynes but also constitutes the first Rh(II)-catalyzed asymmetric intramolecular cycloisomerization of 1,6-diynes. This protocol provides a range of valuable furan-fused dihydropiperidine derivatives with an enantiomerically enriched alkynyl-substituted aza-quaternary stereocenter in high efficiency, complete atom economy, and excellent enantioselectivity (up to 98% ee). Besides, the highly functionalized products could be easily transformed into various synthetically useful building blocks and conjugated with a series of pharmaceutical molecules. The mechanism involving a concerted [3+2] cycloaddition/[1,2]-H shift of the Rh(II) carbenoid intermediate was elucidated by DFT calculations and mechanistic studies. More importantly, the first single crystal of alkyne-dirhodium(II) was obtained to show that a η2-coordinating activation of alkynal by dirhodium(II) was involved. Weak hydrogen bondings between the carboxylate ligands and alkynal were found, which probably made the well-defined paddlewheel-like dirhodium(II) distinctive from other metal complexes in catalyzing this transformation. Furthermore, the origin of the enantioselectivity was elucidated by a Rh2(R-PTAD)4-alkyne complex and additional calculational studies.

Copper-catalysed three-component carboiodination of arynes: Expeditious synthesis of: O -alkynyl aryl iodides

A copper-catalysed three-component iodoalkynylation reaction of arynes for the expeditious and versatile synthesis of o-alkynyl aryl iodides has been developed. Mechanism research shows that the reaction goes through two steps enabled by copper catalysis: the formation of 1-iodo-2-arylacetylene and the insertion of the aryne into a C(sp)-I bond.