443776-94-1

Basic information

• Product Name: 2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde
• Synonyms: 2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde;4-Fluoro-3-forMylphenylboronic acid, pinacol ester
• CAS NO: 443776-94-1
• Molecular Formula: C₁₃H₁₆BFO₃
• Molecular Weight: 250.0737432
• Mol File: 443776-94-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde(443776-94-1)
• EPA Substance Registry System: 2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde(443776-94-1)

Safety Data

• Hazardous Substances Data: 443776-94-1(Hazardous Substances Data)

Usage

General Description

2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde is a chemical compound often utilized in organic chemistry synthesis. It features an aromatic benzaldehyde ring structure for coupling reactions and is fluorinated, which can enhance the properties of the final compounds due to the high electronegativity of the fluorine atom. 2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde also possesses a dioxaborolane group, which is vital in the Suzuki-Miyaura cross-coupling reaction, a common method used to create carbon-carbon bonds in organic synthesis. This chemical compound is commonly used in pharmaceuticals and materials chemistry.

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 374538-01-9 (4-fluoro-3-formylphenyl)boronic acid 
• 93777-26-5 5-bromo-2-fluorobenzaldehyde 
• 73183-34-3 bis(pinacol)diborane 
• 1001200-45-8 3-dibromomethyl-4-fluorobenzeneboronic acid pinacol ester 

Downstream Products

• 1352733-99-3 [2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanol 
• 1544673-73-5 1-[2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine 
• 1544673-57-5 2-[2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]isoindoline-1,3-dione 
• 19434-34-5 2-(phenoxy)benzaldehyde 
• 364354-24-5 2-phenoxy-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzaldehyde 

Relevant articles and documents

Synthesis of boron-containing primary amines

In this study, boron-containing primary amines were synthesized for use as building blocks in the study of peptoids. In the first step, Gabriel synthesis conditions were modified to enable the construction of seven different aminomethylphenyl boronate esters in good to excellent yields. These compounds were further utilized to build peptoid analogs via an Ugi four-component reaction (Ugi-4CR) under microwave irradiation. The prepared Ugi-4CR boronate esters were then successfully converted to the corresponding boronic acids. Finally, the peptoid structures were successfully modified by cross-coupling to aryl/heteroaryl chlorides via a palladium-mediated Suzuki coupling reaction to yield the corresponding derivatives in moderate to good yields.

8-PYRAZINYL-S-SPIROPYRIMIDINETRIONE-OXAZINOQUINOLINE DERIVATIVES AS ANTIBACTERIAL AGENTS

Described herein are antibacterial compounds, methods for making the compounds, pharmaceutical compositions containing the compounds and methods of treating bacterial infections utilizing the compounds and pharmaceutical composition.

Synthesis of para-substituted 3-formyl arylboronic esters

The synthesis of novel para-substituted amino- and phenoxy-3-formylarylboronic acids is described. These compounds are formed by the hitherto unreported nucleophilic aromatic substitution of fluorine with a range of phenols and amines in the presence of a boronic acid moiety. These reactions proceed in moderate to good yields (37-92%) and provide a useful regioselective synthetic route to trisubstituted arylboronates. These compounds are important both as intermediates in organic synthesis and as end products in their own right.