68716-49-4

Basic information

• Product Name: 2-(4-BROMO-PHENYL)-4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLANE
• Synonyms: 2-(4-BROMO-PHENYL)-4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLANE;4-Bromophenylboronic acid,pinacol ester;1,3,2-Dioxaborolane, 2-(4-bromophenyl)-4,4,5,5-tetramethyl-
• CAS NO: 68716-49-4
• Molecular Formula: C₁₂H₁₆BBrO₂
• Molecular Weight: 282.98
• Mol File: 68716-49-4.mol
• Article Data: 88

Chemical Properties

• Melting Point: 69.0 to 73.0 °C
• Boiling Point: 324.147°C at 760 mmHg
• Flash Point: 149.839°C
• Appearance: /
• Density: 1.297g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-(4-BROMO-PHENYL)-4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-BROMO-PHENYL)-4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLANE(68716-49-4)
• EPA Substance Registry System: 2-(4-BROMO-PHENYL)-4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLANE(68716-49-4)

Safety Data

• Hazardous Substances Data: 68716-49-4(Hazardous Substances Data)

Usage

General Description

2-(4-Bromo-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane is a chemical compound with the molecular formula C12H17BO2Br. It is a boronic ester derivative, which contains a boron atom and a bromine atom bonded to a phenyl ring. 2-(4-BROMO-PHENYL)-4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLANE is commonly used as a building block in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and materials science. It is a versatile reagent in Suzuki-Miyaura cross-coupling reactions, which are widely used in the construction of carbon-carbon bonds. Overall, 2-(4-Bromo-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane is an important and valuable chemical in the field of organic chemistry.

InChI:InChI=1/C12H16BBrO2/c1-11(2)12(3,4)16-13(15-11)9-5-7-10(14)8-6-9/h5-8H,1-4H3

Upstream product

• 106-37-6 1.4-dibromobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 
• 73183-34-3 bis(pinacol)diborane 
• 589-87-7 1,4-bromoiodobenzene 
• 106-40-1 4-bromo-aniline 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 22092-92-8 diisopropopylaminoborane 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 106-38-7 para-bromotoluene 
• 106-39-8 bromochlorobenzene 
• 108-86-1 bromobenzene 
• 2890-88-2 (C₂H₅)3N*BCl₃ 

Downstream Products

• 144432-80-4 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1220095-36-2 N-pentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 
• 321903-29-1 1,1-dimethyl-1,3-dihydrobenzo[c][1,2]oxasilole 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 1269230-74-1 3,3-bis(4-bromophenyl)-5,5,6,6-tetramethyl-2-(trimethylsiloxy)-1,4,2-dioxaborinane 
• 1365610-75-8 ethyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butanoate 
• 1335316-49-8 tert-butyl (2S,4S)-2-[5-(4-bromophenyl)-1H-benzimidazol-2-yl]-4-methyl-pyrrolidine-1-carboxylate 
• 54446-36-5 4-bromodiphenylamine 
• 22148-20-5 N-(4-bromophenyl)piperidine 
• 81931-99-9 (bromodifluoromethyl)(4-bromophenyl)thioether 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 457613-56-8 2-(4-bromophenyl)-4,6-diphenylpyrimidine 

Relevant articles and documents

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

Engaging Ag(0) single atoms in silver(I) salts-mediated C-B and C-S coupling under visible light irradiation

Silver(I) salts were found active in the borylation and sulfenylation of aryl iodides under visible light irradiation. The optimized borylation protocol using AgF did not need any additive, operated under very mild conditions, and well tolerated a broad scope of substrates and boron sources. Formation of Ag(0) single atoms (AgSAs) during the borylation reactions was examined using high-angle annular dark field aberration-corrected scanning transmission electron microscope (HAADF AC-STEM) and electron paramagnetic resonance (EPR). The activities of the silver(I) salts were affected by the anions and could be associated with their abilities in formation of AgSAs during the reactions. Kinetic studies showed that the deiodination rate was linearly correlated with the loading of AgSAs, and hence AgSAs were the true catalytic centers for the 1e?-reduction of the C-I moieties. The oxidation state of AgSAs kept 0 in both the resting and the working states. A “work-in-tandem” mechanism involving AgSAs as the catalytic centers and AgNPs as the light absorber to achieve the borylation of aryl iodides under visible light irradiation is proposed. The current approach not only provides an alternative system for borylation and sulfenylation of aryl iodides, but also reveals a new activity of silver(I) salts involving AgSAs under visible light irradiation.

Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron

The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.