178106-74-6

Basic information

• Product Name: (Z)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-bis(4-methoxyphenyl)ethene
• Synonyms: (Z)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-bis(4-methoxyphenyl)ethene
• CAS NO: 178106-74-6
• Molecular Weight: 492.228
• Mol File: 178106-74-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (Z)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-bis(4-methoxyphenyl)ethene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-bis(4-methoxyphenyl)ethene(178106-74-6)
• EPA Substance Registry System: (Z)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-bis(4-methoxyphenyl)ethene(178106-74-6)

Safety Data

• Hazardous Substances Data: 178106-74-6(Hazardous Substances Data)

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 121-43-7 Trimethyl borate 
• 2132-62-9 4,4'-dimethoxydiphenylacetylene 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1338078-45-7 2,3,6,7-tetramethoxy-9,10-bis(4-methoxyphenyl)phenanthrene 
• 1383673-34-4 1,2-bis(4-methoxyphenyl)naphthalene 
• 1383673-42-4 1,2,8,9-tetrakis(4-methoxyphenyl)dibenzo[b,d]thiophene 
• 1383673-41-3 1,2,11,12-tetrakis(4-methoxyphenyl)picene 
• 1091603-70-1 9,10-bis(4-methoxyphenyl)-1,2,3,4,5,6,7,8-octafluorophenanthrene 
• 103162-61-4 9,10-bis (4-methoxyphenyl)phenanthrene 

Relevant articles and documents

The product of catalysed diboration of bis(4-methoxyphenyl)ethyne by bis-(pinacolato-O,O′)diboron

The title compound, (Z)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-bis(4- methoxyphenyl)-ethene, C28H38B2O6, has a cis arrangement of two boronate ester substituents and two 4-methoxyphenyl substituents on its central C=C double bond, which shows a slight twist of ca 8.5°. All four substituents are rotated considerably out of the alkene plane to reduce steric hindrance. The BO2C2 five-membered rings have a twist conformation.

Divergent and Stereoselective Synthesis of Tetraarylethylenes from Vinylboronates

The synthesis of a new tetraborylethylene (TBE) is reported, and its application in the preparation of [4+0]-tetraarylethenes (TAEs) is elucidated. TAEs have widespread applications in material science and supramolecular chemistry due to their aggregation-induced emission (AIE) properties. The divergent and stereoselective synthesis of [3+1]-, [2+2]-, and [2+1+1]-TAEs via multiple couplings of vinylboronates with aryl bromides is demonstrated. These couplings feature a broad substrate scope and excellent functional group compatibility due to mild reaction conditions. Facile access to various tetraarylethenes is provided. This strategy represents an important complement to the conventional methods employed for the synthesis of TAEs, and would be a valuable tool for synthesizing TAE-based molecules useful in functional materials, biological imaging and chemical sensing.

Copper-catalyzed borylation reactions of alkynes and arynes

One, two, three, four: A copper(I)-phosphine complex catalyzes the diborylation of alkynes and arynes, and the tri- or tetraborylation of propargyl ethers (see scheme; pin=pinacolato). In the latter cases, the C-O bond(s) as well as the C≡C bond are borylated in one pot. Furthermore, a diborylation product serves as an intermediate in the efficient synthesis of ortho-terphenyls with pharmacological activity.