(2,4-Difluoro-3-propoxyphenyl)boronic Acid

(2,4-Difluoro-3-propoxyphenyl)boronic Acid

CAS Number: 2096329-68-7
Molecular Formula: C9H11BF2O3
Molecular Weight: 215.99
SMILES Code: OB(C1=CC=C(F)C(OCCC)=C1F)O

Product Introduction
Product Name (2,4-Difluoro-3-propoxyphenyl)boronic acid
CAS Number 2096329-68-7
Molecular Formula C9H11BF2O3
Molecular Weight 215.99
SMILES Code OB(C1=CC=C(F)C(OCCC)=C1F)O
MDL Number MFCD19981527
Pubchem ID 56776673
InChIKey BUFQSDWLWIWVKM-UHFFFAOYSA-N

 

Chemical Properties

 

This arylboronic acid derivative typically exists as a white to off-white crystalline powder,melting at approximately 110-115°C with a predicted boiling point of 339.9°C.The estimated density is 1.25 g/cm³.As a chiral compound(R-configuration),specific optical rotation data requires experimental determination.It exhibits limited water solubility but dissolves readily in polar organic solvents including methanol,ethanol,acetone,DMSO,and DMF.It remains stable under dry,ambient conditions;however,the hydroxymethyl group is susceptible to oxidation,dictating careful storage.

 

Description

 

(2,4-Difluoro-3-propoxyphenyl)boronic acid is a multifunctional coupling partner engineered for precision synthesis.Its structure features a strategic combination of two fluorine atoms(offering electronic modulation and metabolic resistance),a chiral propoxy group(introducing stereochemistry and steric guidance),and a boronic acid handle for cross-coupling.This ensemble of features makes it invaluable for constructing sophisticated chiral molecules where control over both electronic properties and three-dimensional shape is critical.

 

Uses

 

1.Pharmaceutical Synthesis(Core Application)

It serves as a key chiral intermediate for the synthesis of oxazolidinone antibiotics and anti-tumor drugs.The chiral configuration(R-configuration)and difluorophenyl structure can optimize the drug's binding ability to target enzymes,enhance bioavailability,and reduce side effects. Additionally,it can be applied in the R&D of anti-inflammatory and anti-viral drug molecules with chiral skeletons.

 

2.Agrochemical R&D

Utilized in the discovery of next-generation chiral fungicides and herbicides.The fluorine atoms enhance lipophilicity and rainfastness,while the chiral center can lead to enantioselective interactions with target enzymes in pests or weeds,potentially allowing for lower application rates and reduced environmental burden compared to racemic mixtures.

 

3.Functional Material Synthesis

Employed as a monomer in Suzuki polycondensation reactions to produce chiral conjugated polymers and small molecules for organic electronics.The resulting materials are investigated for use in circularly polarized light-emitting diodes(CP-OLEDs)and as chiral selective layers in sensors due to the induced molecular asymmetry from the propoxy group.

 

4.Organic Synthesis Building Block

A sophisticated reagent for asymmetric synthesis and library development.Its boronic acid group enables rapid diversification via cross-coupling,while the pre-installed chirality and fluorine atoms provide a complex,drug-like starting point for parallel synthesis aimed at exploring novel chemical space in medicinal chemistry campaigns.

 

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