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

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

Uses

Used in Organic Synthesis:
4,4,5,5-Tetramethyl-2-(4-phenylethynyl)[1,3,2]dioxaborolane is used as a reagent in organic synthesis for the formation of carbon-carbon and carbon-heteroatom bonds due to its high stability and resistance to hydrolysis, which allows for efficient bond formation in various chemical reactions.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 4,4,5,5-Tetramethyl-2-(4-phenylethynyl)[1,3,2]dioxaborolane is used as an intermediate or a reagent in the synthesis of various drugs, leveraging its unique reactivity to create complex molecular structures necessary for medicinal chemistry.
Used in Agrochemical Development:
4,4,5,5-Tetramethyl-2-(4-phenylethynyl)[1,3,2]dioxaborolane is utilized in the development of agrochemicals, where its ability to form stable bonds is crucial for creating effective and stable pesticides or other agricultural products.
Used in Advanced Material Development:
In the development of advanced materials such as polymers and liquid crystals, 4,4,5,5-Tetramethyl-2-(4-phenylethynyl)[1,3,2]dioxaborolane is used as a key component to create materials with specific properties, such as improved stability or novel optical characteristics, due to its unique structure and reactivity.

Upstream product

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

Downstream Products

• 1313370-73-8 methyl 1,2-diphenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cycloprop-2-enecarboxylate 
• 1849-28-1 1-iodo-4-phenylethynyl-benzene 
• 1220633-35-1 2-(4-(2-phenylethynyl)phenyl)pyridine 
• 370-99-0 4-trifluoromethyldiphenylethyne 
• 405-29-8 (4-fluorophenyl)phenylacetylene 
• 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)] 
• 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 
• 1221823-28-4 (Z)-4,4,5,5-tetramethyl-2-(4-styrylphenyl)-1,3,2-dioxaborolane 
• 1223435-20-8 1-methyl-2-[4-(phenylethynyl)phenyl]-1H-imidazole-4,5-dicarbonitrile 

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.

Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes: Synthesis of unsymmetrical diarylethynes

Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes is described. This reaction not only effectively inhibits the formation of undesired homocoupled products by avoiding the addition of a base, but also exhibits a wide substrate scope to provide a general access to diverse unsymmetrical diarylethynes.

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.

Silver triflate-catalyzed cyclopropenation of internal alkynes with donor-/acceptor-substituted diazo compounds

Silver triflate was found to be an efficient catalyst for the cyclopropenation of internal alkynes using donor-/acceptor-substituted diazo compounds as carbenoid precursors. Highly substituted cyclopropenes, which cannot be synthesized directly via rhodium(II)-catalyzed carbenoid chemistry, can now be readily accessed.

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

Convenient methods for preparing ?-conjugated linkers as building blocks for modular chemistry

Simple, straightforward and optimized procedures for preparing extended ?-conjugated linkers are described. Either unsubstituted or 4-donor substituted ?-linkers bearing a styryl, biphenyl, phenylethenylphenyl, and phenylethynylphenyl ?-conjugated backbone are functionalized with boronic pinacol esters as well as with terminal acetylene moieties allowing their further use as building blocks in Suzuki-Miyaura or Sonogashira coupling reactions.