1415236-88-2

Basic information

• Product Name: 4,4,5,5-Tetramethyl-2-[4-(prop-2-en-1-yloxy)phenyl]-1,3,2-dioxaborolane
• Synonyms: 4,4,5,5-Tetramethyl-2-[4-(prop-2-en-1-yloxy)phenyl]-1,3,2-dioxaborolane
• CAS NO: 1415236-88-2
• Molecular Formula: C₁₅H₂₁BO₃
• Molecular Weight: 260.13644
• Mol File: 1415236-88-2.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 357.5±25.0 °C(Predicted)
• Appearance: /
• Density: 1.01±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 4,4,5,5-Tetramethyl-2-[4-(prop-2-en-1-yloxy)phenyl]-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,5,5-Tetramethyl-2-[4-(prop-2-en-1-yloxy)phenyl]-1,3,2-dioxaborolane(1415236-88-2)
• EPA Substance Registry System: 4,4,5,5-Tetramethyl-2-[4-(prop-2-en-1-yloxy)phenyl]-1,3,2-dioxaborolane(1415236-88-2)

Safety Data

• Hazardous Substances Data: 1415236-88-2(Hazardous Substances Data)

Usage

General Description

4,4,5,5-Tetramethyl-2-[4-(prop-2-en-1-yloxy)phenyl]-1,3,2-dioxaborolane is a chemical compound with the molecular formula C16H23BO2. It is a boronic ester derivative that is commonly used in organic synthesis and medicinal chemistry. 4,4,5,5-Tetramethyl-2-[4-(prop-2-en-1-yloxy)phenyl]-1,3,2-dioxaborolane is a versatile reagent for the Suzuki-Miyaura cross-coupling reaction, which is a widely used method for forming carbon-carbon bonds. It can also be used as a building block for the synthesis of various pharmaceuticals, agrochemicals, and functional materials. Additionally, it has potential applications in the production of liquid crystals, OLEDs, and other electronic devices.

Upstream product

• 25244-30-8 4-(allyloxy)bromobenzene 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 13997-71-2 1-(allyloxy)-4-iodobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 106-95-6 allyl bromide 
• 269409-70-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 
• 27914-60-9 4-allyloxybenzoic acid 
• 13997-70-1 1-allyloxy-4-chlorobenzene 
• 73441-60-8 (4-(allyloxy)phenyl)(methyl)sulfane 
• 67758-84-3 4-allyloxy-N,N-dimethyl-aniline 

Downstream Products

• 501-92-8 4-(prop-2-enyl)phenol 
• 269409-70-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 

Relevant articles and documents

Anomalous reactivity of silylborane: Transition-metal-free boryl substitution of aryl, alkenyl, and alkyl halides with silylborane/alkoxy base systems

An unexpected borylation of organic halides with a silyborane in the presence of an alkoxy base has been observed. This formal nucleophilic boryl substitution can be applied to a broad range of substrates with high functional group compatibility. Even sterically hindered aryl bromides afforded the corresponding boryl compounds in high yields. Preliminary mechanistic studies indicated that this boryl substitution is promoted by neither transition-metal contamination nor a radical-mediated process.

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.

Redox-Neutral Borylation of Aryl Sulfonium Salts via C-S Activation Enabled by Light

Reported here is a novel photoinduced strategy for the borylation of aryl sulfonium salts using bis(pinacolato)diboron as the boron source. This method exploits redox-neutral aryl sulfoniums to gain access to aryl radicals via C-S bond activation upon photoexcitation under transition-metal-free conditions. Therefore, it grants access to diverse arylboronate esters with good performance from easily available aryl sulfoniums accompanied by mild conditions, operational simplicity, and easy scalability.