269410-15-3

Basic information

• Product Name: 2-(2-Fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-Fluoro-4-biphenylboronic acid, pinacol ester;3-Fluoro-4-biphenylboronic acid, pinacol ester;2-(2-Fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl;2-Fluoro-[1,1'-biphenyl]-4-boronicacid,pinacolester98%
• CAS NO: 269410-15-3
• Molecular Formula: C₁₈H₂₀BFO₂
• Molecular Weight: 298.16
• Product Categories: blocks;BoronicAcids
• Mol File: 269410-15-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2-Fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(269410-15-3)
• EPA Substance Registry System: 2-(2-Fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(269410-15-3)

Safety Data

• Hazardous Substances Data: 269410-15-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(2-Fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a building block in the synthesis of various pharmaceuticals. Its reactivity in cross-coupling reactions allows for the creation of complex molecular structures that are integral to the development of new drugs.
Used in Agrochemical Production:
In the agrochemical industry, 2-(2-Fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a key intermediate for the synthesis of pesticides and other agrochemicals. Its role in forming carbon-carbon bonds is essential for constructing the molecular frameworks of these compounds.
Used in Materials Science for OLEDs:
2-(2-Fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a precursor in the production of organic light-emitting diodes (OLEDs). Its properties contribute to the development of advanced optoelectronic devices with improved performance and efficiency.
Used in the Synthesis of Advanced Materials:
Beyond OLEDs, this compound is utilized in the synthesis of other advanced materials for various applications, leveraging its reactivity in cross-coupling reactions to form complex and functional molecular architectures.

Upstream product

• 41604-19-7 1-bromo-3-fluoro-4-phenylbenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 321-60-8 2-fluorobiphenyl 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 178305-99-2 (2-fluoro-[1,1'-biphenyl]-4-yl)boronic acid 

Downstream Products

• 862555-23-5 3-[1-(4-chloro-benzyl)-5-(2-fluoro-biphenyl-4-yl)-3-methyl-1H-indol-2-yl]-2,2-dimethyl-propionic acid methyl ester 

Relevant articles and documents

Iron-catalysed enantioselective Suzuki-Miyaura coupling of racemic alkyl bromides

The first iron-catalysed enantioselective Suzuki-Miyaura coupling reaction has been developed. In the presence of catalytic amounts of FeCl2 and (R,R)-QuinoxP?, lithium arylborates are cross-coupled with tert-butyl α-bromopropionate in an enantioconvergent manner, enabling facile access to various optically active α-arylpropionic acids including several nonsteroidal anti-inflammatory drugs (NSAIDs) of commercial importance. (R,R)-QuinoxP? is specifically able to induce chirality when compared to analogous P-chiral ligands that give racemic products, highlighting the critical importance of transmetalation in the present asymmetric cross-coupling system.

C(sp2)-H Borylation of Fluorinated Arenes Using an Air-Stable Cobalt Precatalyst: Electronically Enhanced Site Selectivity Enables Synthetic Opportunities

Cobalt catalysts with electronically enhanced site selectivity have been developed, as evidenced by the high ortho-to-fluorine selectivity observed in the C(sp2)-H borylation of fluorinated arenes. Both the air-sensitive cobalt(III) dihydride boryl 4-Me-(iPrPNP)Co(H)2BPin (1) and the air-stable cobalt(II) bis(pivalate) 4-Me-(iPrPNP)Co(O2CtBu)2 (2) compounds were effective and exhibited broad functional group tolerance across a wide range of fluoroarenes containing electronically diverse functional groups, regardless of the substitution pattern on the arene. The electronically enhanced ortho-to-fluorine selectivity observed with the cobalt catalysts was maintained in the presence of a benzylic dimethylamine and hydrosilanes, overriding the established directing-group effects observed with precious-metal catalysts. The synthetically useful selectivity observed with cobalt was applied to an efficient synthesis of the anti-inflammatory drug flurbiprofen.

Hydroboronation process

The invention relates to processes for the synthesis of aryl or alkene borates which comprises reacting: (i) an olefinic compound having a halogen or halogen-like substituent in a vinylic substitution position, or (ii) an aromatic ring having a halogen or halogen-like substituent in a ring substitution position, with a disubstituted monohydroborane in the presence of a Group 8-11 metal catalyst. The invention also relates to the use of these borates in coupling reactions. The invention further relates to certain disubstituted monohydroboranes and aryl or alkene borates.