159087-45-3

Basic information

• Product Name: 4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane
• Synonyms: 2-Phenyl-1-ethynylboronic acid pinacol ester;4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane;2-Phenyl-1-ethynylboronic acid pinacol ester 90%;4,4,5,5-tetramethyl-2-(2-phenylethynyl)-1,3,2-dioxaborolane
• CAS NO: 159087-45-3
• Molecular Formula: C₁₄H₁₇BO₂
• Molecular Weight: 228.1
• Product Categories: Alkynyl Boronate Esters;Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Organometallic Reagents
• Mol File: 159087-45-3.mol
• Article Data: 31

Chemical Properties

• Melting Point: 49-68 °C
• Boiling Point: 265.4±23.0 °C(Predicted)
• Appearance: /
• Density: 1.03±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane(159087-45-3)
• EPA Substance Registry System: 4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane(159087-45-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 159087-45-3(Hazardous Substances Data)

Usage

General Description

4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane is a chemical compound with the molecular formula C14H17BO2. It is a boronic ester, which is commonly used in organic synthesis as a building block for pharmaceuticals, agrochemicals, and materials science. 4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane has a unique structure with a boron atom attached to a phenyl group and an ethynyl group, making it an important reagent in various cross-coupling reactions. It is a white to yellow solid with a melting point of 70-75°C and is soluble in organic solvents such as dichloromethane and tetrahydrofuran. 4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane is widely used in the field of organic chemistry for the synthesis of complex organic molecules.

Upstream product

• 3240-11-7 Phenylacetylene-d1 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 536-74-3 phenylacetylene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1086138-68-2 C₁₀H₇BO₃ 

Downstream Products

• 863422-37-1 3,6-bis(3,5-dimethylpyrazol-1-yl)-4-phenyl-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyridazine 
• 958633-19-7 (Z)-4,4,5,5-tetramethyl-2-(2-phenyl-1-buten-1-yl)-1,3,2-dioxaborolane 
• 865999-25-3 (E)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1,2-diphenyl-1-butene 
• 910875-17-1 methyl 2-bromo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-carboxylate 
• 919197-90-3 3,6-dichloro-4-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridazine 
• 873868-21-4 (C₅H₅)Co(C₆H₂)(C₆H₅)2(BC₆H₁₂O₂)2C₃H₆ 
• 873868-22-5 (C₅H₅)Co(C₁₀H₁₀(C₆H₅)2((CH₃)4C₂O₂B)2) 
• 873806-32-7 (C₅H₅)Co(C₆H₃((CH₃)4C₂O₂B)2(C₆H₅)3) 
• 873806-34-9 (C₅H₅)Co(C₆H₃((CH₃)4C₂O₂B)2(C₆H₅)2(Si(CH₃)3)) 
• 873806-35-0 (C₅H₅)Co(C₆H₃((CH₃)4C₂O₂B)2(C₆H₅)2(Si(CH₃)3)) 
• 873806-26-9 (C₅H₅)Co(C₆H₂)(C₆H₅)2(BC₆H₁₂O₂)2C₂H₄O 
• 873806-30-5 (C₅H₅)Co(C₆H₂((CH₃)4C₂O₂B)2(C₆H₅)4) 
• 873806-36-1 (C₅H₅)Co(C₆H₃((CH₃)4C₂O₂B)2(C₆H₅)2(Sn(C₄H₉)3)) 
• 873806-37-2 (C₅H₅)Co(C₆H₃((CH₃)4C₂O₂B)2(C₆H₅)2(Sn(C₄H₉)3)) 

Relevant articles and documents

Substituent effects in Carboni-Lindsey reactions of 1,2,4,5-tetrazines and aryl-substituted alkynylboronates

Evidence for an inverse-electron-demand cycloaddition of tetrazines with alkynylboronates is presented by the reaction of 3,6-bis(3,5-dimethyl-1H- pyrazol-1-yl)-1,2,4,5-tetrazine with aryl-alkynylboronate substrates bearing various para substituents. Geor

Aluminium-Catalyzed C(sp)?H Borylation of Alkynes

Historically used in stoichiometric hydroalumination chemistry, recent advances have transformed aluminium hydrides into versatile catalysts for the hydroboration of unsaturated multiple bonds. This catalytic ability is founded on the defining reactivity of aluminium hydrides with alkynes and alkenes: 1,2-hydroalumination of the unsaturated π-system. This manuscript reports the aluminium hydride catalyzed dehydroborylation of terminal alkynes. A tethered intramolecular amine ligand controls reactivity at the aluminium hydride centre, switching off hydroalumination and instead enabling selective reactions at the alkyne C?H σ-bond. Chemoselective C?H borylation was observed across a series of aryl- and alkyl-substituted alkynes (21 examples). On the basis of kinetic and density functional theory studies, a mechanism in which C?H borylation proceeds by σ-bond metathesis between pinacolborane (HBpin) and alkynyl aluminium intermediates is proposed.

ZnBr2-Catalyzed Dehydrogenative Borylation of Terminal Alkynes

The simple, commercially available ZnBr2 has been successfully employed as a highly efficient and chemoselective catalyst for the dehydrogenative borylation of terminal alkynes with HBpin under mild conditions. It shows a good tolerance toward various functional groups such as aryl, alkyl, heteroaryl, etc. The plausible reaction mechanism has been investigated based on the corresponding stoichiometric experiments and DFT calculations.