1190376-20-5

Basic information

• Product Name: 4,4,5,5-Tetramethyl-2-(4-phenylethynyl)[1,3,2]dioxaborolane
• Synonyms: 4,4,5,5-Tetramethyl-2-(4-phenylethynyl)[1,3,2]dioxaborolane;4,4,5,5-Tetramethyl-2-(4-phenylethynyl-phenyl)-[1,3,2]dioxaborolane;4,4,5,5-tetramethyl-2-[4-(2-phenylethynyl)phenyl]-1,3,2-dioxaborolane
• CAS NO: 1190376-20-5
• Molecular Formula: C₂₀H₂₁BO₂
• Molecular Weight: 304.19054
• Mol File: 1190376-20-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 96-100°C
• Boiling Point: 428.7±28.0 °C(Predicted)
• Appearance: /
• Density: 1.08±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 4,4,5,5-Tetramethyl-2-(4-phenylethynyl)[1,3,2]dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,5,5-Tetramethyl-2-(4-phenylethynyl)[1,3,2]dioxaborolane(1190376-20-5)
• EPA Substance Registry System: 4,4,5,5-Tetramethyl-2-(4-phenylethynyl)[1,3,2]dioxaborolane(1190376-20-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1190376-20-5(Hazardous Substances Data)

Usage

General Description

4,4,5,5-Tetramethyl-2-(4-phenylethynyl)[1,3,2]dioxaborolane is a chemical compound that contains boron and carbon elements. It is commonly used in organic synthesis, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. 4,4,5,5-Tetramethyl-2-(4-phenylethynyl)[1,3,2]dioxaborolane is known for its high stability and resistance to hydrolysis, making it a valuable reagent in various chemical reactions. Additionally, 4,4,5,5-Tetramethyl-2-(4-phenylethynyl)[1,3,2]dioxaborolane is also utilized in the production of pharmaceuticals and agrochemicals, as well as in the development of advanced materials such as polymers and liquid crystals. Its unique structure and reactivity make it a versatile and important component in modern chemical research and industrial applications.

Upstream product

• 536-74-3 phenylacetylene 
• 73852-88-7 2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1034287-04-1 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetylene 
• 591-50-4 iodobenzene 
• 68716-49-4 p-bromophenylboronic acid pinacol ester 
• 4440-01-1 lithium phenylacetylide 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 455-32-3 benzoyl fluoride 
• 870238-65-6 ((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethynyl)trimethylsilane 

Downstream Products

• 1223435-20-8 1-methyl-2-[4-(phenylethynyl)phenyl]-1H-imidazole-4,5-dicarbonitrile 
• 1313370-73-8 methyl 1,2-diphenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cycloprop-2-enecarboxylate 
• 1221823-28-4 (Z)-4,4,5,5-tetramethyl-2-(4-styrylphenyl)-1,3,2-dioxaborolane 
• 1337541-79-3 4,4,5,5-tetramethyl-2-(4-phenethylphenyl)-1,3,2-dioxaborolane 
• 943858-44-4 4,4,5,5-tetramethyl-2-[4-[(1E)-2-phenylethenyl]phenyl]-1,3,2-dioxaborolane 
• 1352608-67-3 [(η4-C4(C6H4-4-B(OCMe2)2)2Ph2)Co(η5-C5H5)] 
• 1352608-49-1 [(η4-C4(C6H4-4-B(OCMe2)2)2Ph2)Co(η5-C5H5)] 
• 1220633-35-1 2-(4-(2-phenylethynyl)phenyl)pyridine 
• 370-99-0 4-trifluoromethyldiphenylethyne 
• 1849-28-1 1-iodo-4-phenylethynyl-benzene 
• 405-29-8 (4-fluorophenyl)phenylacetylene 

Relevant articles and documents

Merging Iridium-Catalyzed C-H Borylations with Palladium-Catalyzed Cross-Couplings Using Triorganoindium Reagents

A versatile and efficient method to prepare borylated arenes furnished with alkyl, alkenyl, alkynyl, aryl, and heteroaryl functional groups is developed by merging Ir-catalyzed C-H borylations (CHB) with a chemoselective palladium-catalyzed cross-coupling of triorganoindium reagents (Sarandeses-Sestelo coupling) with aryl halides bearing a boronic ester substituent. Using triorganoindium cross-coupling reactions to introduce unsaturated moieties enables the synthesis of borylated arenes that would be difficult to access through the direct application of the CHB methodology. The sequential double catalyzed procedure can be also performed in one vessel.

Mild, Selective Ru-Catalyzed Deuteration Using D2O as a Deuterium Source

A method for the selective deuteration of polyfunctional organic molecules using catalytic amounts of [RuCl2(PPh3)3] and D2O as a deuterium source is presented. Through variation of additives like CuI, KOH, and various amounts of zinc powder, orthogonal chemoselectivities in the deuteration process are observed. Mechanistic investigation indicates the presence of different, defined Ru-complexes under the given specific conditions.

Introduction of two anthracene moieties into perylenebis(dicarboximide) Core by suzukimiyaura coupling toward construction of donoracceptordonor arrays

To create new φ-conjugated compounds having a donoracceptordonor array, two 4-(9-anthrylethynyl)phenyl groups were introduced into a perylenebis(dicarboximide) structure at 1,6- or 1,7-positions by the SuzukiMiyaura coupling of corresponding dibromoperyle