138738-20-2

Basic information

• Product Name: 2-methoxy-9,10-diphenyl-9,10-epoxyanthracene
• Synonyms: 2-methoxy-9,10-diphenyl-9,10-epoxyanthracene
• CAS NO: 138738-20-2
• Molecular Weight: 376.455
• Mol File: 138738-20-2.mol

Chemical Properties

• CAS DataBase Reference: 2-methoxy-9,10-diphenyl-9,10-epoxyanthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methoxy-9,10-diphenyl-9,10-epoxyanthracene(138738-20-2)
• EPA Substance Registry System: 2-methoxy-9,10-diphenyl-9,10-epoxyanthracene(138738-20-2)

Safety Data

• Hazardous Substances Data: 138738-20-2(Hazardous Substances Data)

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 5471-63-6 1,3-diphenylisobenzofuran 
• 138719-96-7 2-bromo-5-methoxyphenyl trifluoromethanesulfonate 

Relevant articles and documents

New efficient protocol for aryne generation. Selective synthesis of differentially protected 1,4,5-naphthalenetriols

Arynes are generated cleanly and rapidly by halogen-lithium exchange of ortho-haloaryl triflates with n-BuLi at -78°C. [2+4]-Cycloaddition of α-alkoxyaryne with 2-methoxyfuran proceeded regioselectively (head-to-head) to afford 1,4,5-naphthalenetriols.

Synthesis of 9,10-Diarylanthracenes via Mg(TMP) 2 ·2LiCl-Mediated Benzyne Generation/[4+2] Cycloaddition and Deoxygenation of 9,10-Epoxyanthracene Intermediates

A new synthetic route to functionalized 9,10-diarylanthracenes has been developed. 9,10-Epoxyanthracene intermediates were prepared by [4+2] cycloaddition of 1,3-diarylisobenzofuran with a variety of functionalized benzyne intermediates, which were obtained by Mg(TMP) 2 ·2LiCl-mediated benzyne generation. For the cleavage of the resultant 9,10-epoxyanthracene intermediates, we developed mild deoxygenation conditions using a combination of trifluoroacetic acid and Et 3 SiH. The utility of this sequence was demonstrated by application to the synthesis of 5,7,12,14-tetraphenylpentacene.

Generation and suppression of 3-/4-functionalized benzynes using zinc ate base (TMP-Zn-ate): New approaches to multisubstituted benzenes

We present full details of our new methods for preparing functionalized benzynes with lithium di-alkyl(2,2,6,6-tetramethylpiperidino)zincate (R 2Zn(TMP)Li) through deprotonative zincation as a key reaction. In this system, by choosing appropriate ligands for the zincate, either regioselective zincation of functionalized haloaromatics or the generation of substituted benzynes can be controlled in good yields with excellent chemoselectivity, using the same substrate. Zincation with tBu 2Zn(TMP)Li followed by electrophilic trapping or zincation with Me2Zn(TMP)Li followed by nucleophilic or diene trapping is shown to be a powerful tool for the chemoselective preparation of 1,2,3-/1,2,4- trisubstituted benzene derivatives. These methods offer far greater generality than previous methods for the synthesis of multifunctionalized benzenes. Computational/theoretical studies of the reaction mechanism of this unique benzyne formation indicated that preferential coordination of the dialkylzinc moiety of zincate to halogen is the reason for the reduced activation energy of the elimination, that is, for the formation of the benzyne. The role of the ligands on Zn in accelerating/decelerating the elimination is also discussed.