183589-09-5

Basic information

• Product Name: Phenol, 2-(phenylethynyl)-, acetate
• CAS NO: 183589-09-5
• Molecular Formula: C16H12O2
• Molecular Weight: 236.27
• Mol File: 183589-09-5.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: Phenol, 2-(phenylethynyl)-, acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 2-(phenylethynyl)-, acetate(183589-09-5)
• EPA Substance Registry System: Phenol, 2-(phenylethynyl)-, acetate(183589-09-5)

Safety Data

• Hazardous Substances Data: 183589-09-5(Hazardous Substances Data)

Upstream product

• 536-74-3 phenylacetylene 
• 50-78-2 aspirin 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 1829-37-4 o-bromophenyl acetate 
• 32865-61-5 2-iodophenyl acetate 

Downstream Products

• 92151-73-0 2-phenylethynylphenol 
• 13448-97-0 methyl 2-phenylbenzofuran-3-carboxylate 
• 200941-12-4 Bromo-acetic acid 2-phenylethynyl-phenyl ester 
• 1191950-62-5 2-(phenyl)-3-(phenylsulfanyl)benzo[b]furan 
• 37883-72-0 2-phenylbenzo[b]furan-3-carbonitrile 
• 92104-01-3 2-phenyl-3-bromobenzo[b]furan 
• 246230-86-4 3-iodo-2-phenylbenzo[b]furan 
• 1839-72-1 2-phenylbenzofuran 
• 1310802-25-5 C₁₆H₁₆O₃ 
• 1581275-98-0 C₂₀H₁₃BO₃ 
• 1581275-99-1 2-(2-phenylbenzofuran-3-yl)benzo[d][1,3,2]dioxaborole 
• 1581276-22-3 C₁₉H₁₆BNO₅ 
• 4265-21-8 3-acetyl-2-phenylbenzofuran 

Relevant articles and documents

Palladium-catalyzed decarbonylative sonogashira coupling of terminal alkynes with carboxylic acids

A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxylic acids including those bioactive ones could couple readily with various terminal alkynes, thus providing a relative general method for preparing internal alkynes.

Alkoxyboration: Ring-closing addition of B-O σ bonds across alkynes

For nearly 70 years, the addition of boron-X σ bonds to carbon-carbon multiple bonds has been employed in the preparation of organoboron reagents. However, the significantly higher strength of boron-oxygen bonds has thus far precluded their activation for addition, preventing a direct route to access a potentially valuable class of oxygen-containing organoboron reagents for divergent synthesis. We herein report the realization of an alkoxyboration reaction, the addition of boron-oxygen σ bonds to alkynes. Functionalized O-heterocyclic boronic acid derivatives are produced using this transformation, which is mild and exhibits broad functional group compatibility. Our results demonstrate activation of this boron-O σ bond using a gold catalysis strategy that is fundamentally different from that used previously for other boron addition reactions.

A concise route to dihydrobenzo[b]furans: Formal total synthesis of (+)-lithospermic acid

A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH4Cl) provides a convergent and modular synthetic route to trans-2-aryl-2,3-dihydrobenzo[b]furan- 3-carboxylates, which are a structural feature of numerous biologically active natural products. This versatile strategy was applied to the formal total synthesis of the anti-HIV natural product (+)-lithospermic acid.