171290-51-0

Basic information

• Product Name: 2-methyl-4-(3,5-dimethoxyphenyl)-3-butyn-2-ol
• Synonyms: 2-methyl-4-(3,5-dimethoxyphenyl)-3-butyn-2-ol
• CAS NO: 171290-51-0
• Molecular Weight: 220.268
• Mol File: 171290-51-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-methyl-4-(3,5-dimethoxyphenyl)-3-butyn-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-4-(3,5-dimethoxyphenyl)-3-butyn-2-ol(171290-51-0)
• EPA Substance Registry System: 2-methyl-4-(3,5-dimethoxyphenyl)-3-butyn-2-ol(171290-51-0)

Safety Data

• Hazardous Substances Data: 171290-51-0(Hazardous Substances Data)

Upstream product

• 25245-27-6 1-iodo-3,5-dimethoxybenzene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 

Downstream Products

• 171290-52-1 1-Ethynyl-3,5-dimethoxy-benzene 

Relevant articles and documents

One-pot synthesis of unsymmetrical 1,3-butadiyne derivatives and their application in the synthesis of unsymmetrical 2,5-diarylthiophenes

A one-pot protocol was developed for the synthesis of unsymmetrical 1,3-butadiynes. The procedure is based on two sequential reactions: deprotection of R–C≡C–C≡C– C(Me)2OH derivatives in a retro-Favorskii reaction to furnish a terminal 1,3-butadiyne compound, which reacted with aryl iod-ides in a Sonogashira-type cross-coupling reaction catalyzed by Pd(PPh3)4 and CuI, using TBAOH as activator and toluene as solvent under reflux for 10 min. We also studied in situ thiocycli-zation of 1,3-butadiynes, leading to unsymmetrical 2,5-diaryl-thiophenes. The principal features of this method are operational simplicity, good substrate scope, very fast reaction, and high yields.

Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions

Two efficient protocols for the palladium-catalyzed synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides in the absence of copper were developed. A simple catalytic system consisting of Pd(OAc)2 and P(p-tol)3 using DBU as the base and THF as the solvent was found to be highly effective for the coupling reaction of 2-methyl-3-butyn-2-ol (4) with a wide range of aryl bromides in good to excellent yields. Analogously, the synthesis of aryl-2-methyl-3-butyn-2-ols was performed also through the decarboxylative coupling reaction of 4-hydroxy-4-methyl-2-pentynoic acid with aryl bromides, using a catalyst containing Pd(OAc)2 in combination with SPhos or XPhos in the presence of tetra-n-butylammonium fluoride (TBAF) as the base and THF as the solvent. Therefore, new efficient approaches to the synthesis of terminal acetylenes from widely available aryl bromides rather than expensive iodides and using 4 or propiolic acid rather than TMS-acetylene as inexpensive alkyne sources are described.