1256355-30-2

Basic information

• Product Name: 5-Fluoro-2-formylphenylboronic acid
• Synonyms: 5-Fluoro-2-formylbenzeneboronic acid
• CAS NO: 1256355-30-2
• Molecular Formula: C₇H₆BFO₃
• Molecular Weight: 168
• Mol File: 1256355-30-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 379.8°C at 760 mmHg
• Flash Point: 173.8°C
• Appearance: /
• Density: 1.778g/cm³
• Vapor Pressure: 2.49E-07mmHg at 25°C
• Refractive Index: 1.295
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.15±0.53(Predicted)
• CAS DataBase Reference: 5-Fluoro-2-formylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Fluoro-2-formylphenylboronic acid(1256355-30-2)
• EPA Substance Registry System: 5-Fluoro-2-formylphenylboronic acid(1256355-30-2)

Safety Data

• Hazard Codes: C:Corrosive
• Statements: R34:
• Safety Statements: S26:; S36/37/39:; S45:
• Hazardous Substances Data: 1256355-30-2(Hazardous Substances Data)

Usage

General Description

5-Fluoro-2-formylphenylboronic acid is a chemical compound with the formula C7H6BFO3. It is a boronic acid derivative with a fluorine atom and a formyl group attached to a phenyl ring. 5-Fluoro-2-formylphenylboronic acid is an important intermediate in the synthesis of various pharmaceuticals, agrochemicals, and functional materials. It is commonly used in organic synthesis as a building block for constructing complex molecules. The boronic acid functional group allows for easy manipulation and modification of the compound, making it a versatile tool for creating new chemical entities. Its unique structure and reactivity make it a valuable tool in medicinal and synthetic chemistry.

InChI:InChI=1/C15H3F29O5/c16-2(1-45,7(22,23)24)46-13(39,40)4(19,9(28,29)30)48-15(43,44)6(21,11(34,35)36)49-14(41,42)5(20,10(31,32)33)47-12(37,38)3(17,18)8(25,26)27/h45H,1H2

Upstream product

• 150-46-9 triethyl borate 
• 1239518-71-8 2-bromo-4-fluorobenzaldehyde dimethyl acetal 
• 59142-68-6 2-bromo-4-fluorobenzaldehyde 
• 121-43-7 Trimethyl borate 
• 1844839-22-0 4-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 40138-16-7 2-formylbenzene boronic acid 

Downstream Products

• 1433030-15-9 2'-benzoyl-5-fluoro-[1,1'-biphenyl]-2-carbaldehyde 
• 1589546-24-6 C₂₉H₂₀FO₂P 
• 1611486-18-0 N-[2-cyano-1-(5'-fluoro-2'-formylbiphenyl-2-yl)allyl]benzamide 

Relevant articles and documents

A simple quantitative chiral analysis of amino acid esters by fluorine-19 nuclear magnetic resonance using the modified James–Bull method

A simple chiral analysis of amino acid esters by fluorine-19 nuclear magnetic resonance (19F?NMR) through the modified James–Bull method is described. Thus, amino acid ester acid salt was treated with 5-fluoro-2-formylphenylboronic acid and (S)-BINOL in the presence of triethylamine (TEA) and MS4A for 10?minutes. The reaction mixture was analysed by 19F?NMR directly to afford good quantifications.

Design and enantioselective synthesis of 3-(α-acrylic acid) benzoxaboroles to combat carbapenemase resistance

Chiral 3-substituted benzoxaboroles were designed as carbapenemase inhibitors and efficiently synthesisedviaasymmetric Morita-Baylis-Hillman reaction. Some of the benzoxaboroles were potent inhibitors of clinically relevant carbapenemases and restored the activity of meropenem in bacteria harbouring these enzymes. Crystallographic analyses validate the proposed mechanism of binding to carbapenemases,i.e.in a manner relating to their antibiotic substrates. The results illustrate how combining a structure-based design approach with asymmetric catalysis can efficiently lead to potent β-lactamase inhibitors and provide a starting point to develop drugs combatting carbapenemases.

Lewis or Br?nsted? A Rectification of the Acidic and Aromatic Nature of Boranol-Containing Naphthoid Heterocycles

Boron-containing heterocycles are important in a variety of applications from drug discovery to materials science; therefore a clear understanding of their structure and reactivity is desirable to optimize these functions. Although the boranol (B-OH) unit of boronic acids behaves as a Lewis acid to form a tetravalent trihydroxyborate conjugate base, it has been proposed that pseudoaromatic hemiboronic acids may possess sufficient aromatic character to act as Br?nsted acids and form a boron oxy conjugate base, thereby avoiding the disruption of ring aromaticity that would occur with a tetravalent boronate anion. Until now no firm evidence existed to ascertain the structure of the conjugate base and the aromatic character of the boron-containing ring of hemiboronic "naphthoid"isosteres. Here, these questions are addressed with a combination of experimental, spectroscopic, X-ray crystallographic, and computational studies of a series of model benzoxazaborine and benzodiazaborine naphthoids. Although these hemiboronic heterocycles are unambiguously shown to behave as Lewis acids in aqueous solutions, boraza derivatives possess partial aromaticity provided their nitrogen lone electron pair is sufficiently available to participate in extended delocalization. As demonstrated by dynamic exchange and crossover experiments, these heterocycles are stable in neutral aqueous medium, and their measured pKa values are consistent with the ability of the endocyclic heteroatom substituent to stabilize a partial negative charge in the conjugate base. Altogether, this study corrects previous inaccuracies and provides conclusions regarding the properties of these compounds that are important toward the methodical application of hemiboronic and other boron heterocycles in catalysis, bioconjugation, and medicinal chemistry.