183677-72-7

Basic information

• Product Name: 1,3,2-Dioxaborinane, 5,5-dimethyl-2-[4-[(trimethylsilyl)ethynyl]phenyl]-
• CAS NO: 183677-72-7
• Molecular Formula: C16H23BO2Si
• Molecular Weight: 286.254
• Mol File: 183677-72-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,3,2-Dioxaborinane, 5,5-dimethyl-2-[4-[(trimethylsilyl)ethynyl]phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2-Dioxaborinane, 5,5-dimethyl-2-[4-[(trimethylsilyl)ethynyl]phenyl]-(183677-72-7)
• EPA Substance Registry System: 1,3,2-Dioxaborinane, 5,5-dimethyl-2-[4-[(trimethylsilyl)ethynyl]phenyl]-(183677-72-7)

Safety Data

• Hazardous Substances Data: 183677-72-7(Hazardous Substances Data)

Usage

Type of compound

Boronic ester

Structure

Contains a boron atom bonded to two oxygen atoms and a hydrocarbon group

Functional groups

Phenyl and ethynyl groups

Applications

a. Organic synthesis
b. Medicinal chemistry
c. Suzuki-Miyaura cross-coupling reactions (construction of carbon-carbon bonds in organic molecules)

Reactivity

a. Useful for reactions involving aryl and alkynyl compounds
b. Versatile compound with applications in various organic synthesis processes

Upstream product

• 1066-54-2 trimethylsilylacetylene 
• 589-87-7 1,4-bromoiodobenzene 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 5467-74-3 4-Bromophenylboronic acid 
• 183677-71-6 2-(4-bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane 

Downstream Products

• 944741-32-6 {5-[4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)-phenylethynyl]naphthalen-1-yl}dimethylamine 
• 944741-30-4 {4-[4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)-phenylethynyl]naphthalen-1-yl}dimethylamine 
• 944741-36-0 3-[4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)-phenylethynyl]quinoline 
• 944741-34-8 {6-[4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)-phenylethynyl]naphthalen-2-yl}dimethylamine 
• 183677-69-2 2,2-dimethylpropane-1,3-diyl 4-ethynylphenyl boronate 

Relevant articles and documents

Alkynyl Moiety for Triggering 1,2-Metallate Shifts: Enantiospecific sp2–sp3 Coupling of Boronic Esters with p-Arylacetylenes

The enantiospecific coupling of secondary and tertiary boronic esters to aromatics has been investigated. Using p-lithiated phenylacetylenes and a range of boronic esters coupling has been achieved by the addition of N-bromosuccinimide (NBS). The alkyne functionality of the intermediate boronate complex reacts with NBS triggering the 1,2-migration of the group on boron to carbon giving a dearomatized bromoallene intermediate. At this point elimination and rearomatization occurs with neopentyl boronic esters, giving the coupled products. However, using pinacol boronic esters, the boron moiety migrates to the adjacent carbon resulting in formation of ortho boron-incorporated coupled products. The synthetic utility of the boron incorporated product has been demonstrated by orthogonal transformation of both the alkyne and boronic ester functionalities.

Effect of extended conjugation with a phenylethynyl group on the fluorescence properties of water-soluble arylboronic acids

Boronic acids that change fluorescence properties upon sugar binding are very important reporter units for the development of small molecule lectin mimics (boronolectins). Aimed at developing long wavelength fluorescent boronic acid reporter compounds, we