269410-07-3

Basic information

• Product Name: 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene
• Synonyms: 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene;2,2'-(1,2-Phenylene)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane];1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzene
• CAS NO: 269410-07-3
• Molecular Formula: C₁₈H₂₈B₂O₄
• Molecular Weight: 330.03452
• Mol File: 269410-07-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 114.0 to 118.0 °C
• Boiling Point: 426.9±28.0 °C(Predicted)
• Appearance: /
• Density: 1.03±0.1 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene(269410-07-3)
• EPA Substance Registry System: 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene(269410-07-3)

Safety Data

• Hazardous Substances Data: 269410-07-3(Hazardous Substances Data)

Usage

General Description

1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene is a chemical compound with the molecular formula C24H32B2O4. It is a type of boron-containing compound known as a boronic ester, which are widely used in organic synthesis and pharmaceuticals. This specific compound is used as a reactant in the synthesis of organic materials and fine chemicals. It acts as a powerful reagent for cross-coupling reactions, where it forms bonds between carbon atoms. It is also used in the formation of complex molecules and in the production of pharmaceuticals, agrochemicals, and electronic materials. Additionally, it is utilized in the production of various advanced materials, such as organic light-emitting diodes and liquid crystals. Overall, 1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene is a highly versatile and valuable compound with a wide range of applications in the field of organic chemistry and materials science.

Upstream product

• 583-55-1 1-Bromo-2-iodobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 583-53-9 2,3-dibromobenzene 
• 615-42-9 1,2-Diiodobenzene 
• 95-50-1 1,2-dichloro-benzene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 73183-34-3 bis(pinacol)diborane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 269410-06-2 2-(2-bromophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 
• 195062-59-0 2-methylphenylboronic acid pinacol ester 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 367-11-3 ortho-difluorobenzene 

Downstream Products

• 525-18-8 10,12-dihydroindeno<2,1-b>fluorene 
• 86-73-7 9H-fluorene 
• 1221184-53-7 1,2-di(thiophen-3-yl)benzene 
• 914675-52-8 2‐{[1,1'‐biphenyl]‐2‐yl}‐4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane 
• 84-15-1 o-terphenyl 
• 1221184-57-1 4'-acetyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl 
• 93232-29-2 4,4’-diacetyl-o-terphenyl 
• 206-44-0 fluoranthene 
• 1449133-19-0 C₂₂H₂₃BO₂ 
• 1221184-55-9 methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-2'-carboxylate 
• 1221184-56-0 9-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phenanthrene 
• 217-59-4 triphenylene 
• 17181-04-3 9-styryl-phenanthrene 
• 85-01-8 phenanthrene 

Relevant articles and documents

Singly and Doubly 1,2-Phenylene-Inserted Porphyrin Arch-Tape Dimers: Synthesis and Highly Contorted Structures

Singly and doubly 1,2-phenylene-inserted NiII porphyrin arch-tape dimers 3 and 9 were synthesized from the corresponding β-to-β 1,2-phenylene-bridged NiII porphyrin dimers 5 and 11 via Ni0-mediated reductive cyclization an

Visible-Light-Induced Ni-Catalyzed Radical Borylation of Chloroarenes

A highly selective and general photoinduced C-Cl borylation protocol that employs [Ni(IMes)2] (IMes = 1,3-dimesitylimidazoline-2-ylidene) for the radical borylation of chloroarenes is reported. This photoinduced system operates with visible light (400 nm) and achieves borylation of a wide range of chloroarenes with B2pin2 at room temperature in excellent yields and with high selectivity, thereby demonstrating its broad utility and functional group tolerance. Mechanistic investigations suggest that the borylation reactions proceed via a radical process. EPR studies demonstrate that [Ni(IMes)2] undergoes very fast chlorine atom abstraction from aryl chlorides to give [NiI(IMes)2Cl] and aryl radicals. Control experiments indicate that light promotes the reaction of [NiI(IMes)2Cl] with aryl chlorides generating additional aryl radicals and [NiII(IMes)2Cl2]. The aryl radicals react with an anionic sp2-sp3 diborane [B2pin2(OMe)]- formed from B2pin2 and KOMe to yield the corresponding borylation product and the [Bpin(OMe)]?- radical anion, which reduces [NiII(IMes)2Cl2] under irradiation to regenerate [NiI(IMes)2Cl] and [Ni(IMes)2] for the next catalytic cycle.

Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water

A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.