94838-88-7

Basic information

• Product Name: 2-FORMYL-4,5-METHYLENEDIOXYPHENYLBORONIC ACID
• Synonyms: (2-FORMYL-4,5-METHYLENEDIOXY)BENZENEBORONIC ACID;2-FORMYL-4,5-METHYLENEDIOXYPHENYLBORONIC ACID;6-FORMYLBENZO[D][1,3]DIOXOL-5-YLBORONIC ACID;(6-formyl-1,3-benzodioxol-5-yl)boronic acid
• CAS NO: 94838-88-7
• Molecular Formula: C₈H₇BO₅
• Molecular Weight: 193.95
• Product Categories: blocks;BoronicAcids;Aldehyde;Aryl;Organoborons;Aldehydes;Aryl Boronic Acids;Boronic Acids;Boronic Acids and Derivatives;Building Blocks;C8;Carbonyl Compounds;Chemical Synthesis;Monosubstituted Aryl Boronic Acids;Organic Building Blocks;Organometallic Reagents
• Mol File: 94838-88-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 231-233
• Boiling Point: 434.3 °C at 760 mmHg
• Flash Point: 216.5 °C
• Appearance: /
• Density: 1.49 g/cm³
• Vapor Pressure: 2.59E-08mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: 2-8°C
• PKA: 8.13±0.20(Predicted)
• CAS DataBase Reference: 2-FORMYL-4,5-METHYLENEDIOXYPHENYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FORMYL-4,5-METHYLENEDIOXYPHENYLBORONIC ACID(94838-88-7)
• EPA Substance Registry System: 2-FORMYL-4,5-METHYLENEDIOXYPHENYLBORONIC ACID(94838-88-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 94838-88-7(Hazardous Substances Data)

Usage

Description

2-FORMYL-4,5-METHYLENEDIOXYPHENYLBORONIC ACID is an organic compound that serves as a versatile reactant in various chemical reactions and synthesis processes. It is characterized by the presence of a formyl group, a methylenedioxy bridge, and a phenylboronate moiety, which contribute to its unique reactivity and applications in organic chemistry.

Uses

Used in Pharmaceutical Industry:
2-FORMYL-4,5-METHYLENEDIOXYPHENYLBORONIC ACID is used as a reactant for the enantioselective preparation of indenamines through cationic palladium complex-catalyzed tandem annulation with alkynes. This process is crucial for the synthesis of biologically active compounds and the development of new pharmaceuticals.
Used in Chemical Synthesis:
2-FORMYL-4,5-METHYLENEDIOXYPHENYLBORONIC ACID is used as a reactant for the stereoselective preparation of indenol derivatives via cationic palladium complex-catalyzed diastereoselective tandem annulation. This method allows for the creation of specific stereoisomers, which are important in the synthesis of complex organic molecules and chiral compounds.
Used in Organic Chemistry Research:
2-FORMYL-4,5-METHYLENEDIOXYPHENYLBORONIC ACID is used in the synthesis of oxazoline-substituted potassium organotrifluoroborates. These compounds are valuable intermediates in organic synthesis and can be used to construct a variety of functionalized molecules.
Used in Antitumor Agent Synthesis:
2-FORMYL-4,5-METHYLENEDIOXYPHENYLBORONIC ACID is used in the preparation of aristolactam analogs, which are potential antitumor agents. 2-FORMYL-4,5-METHYLENEDIOXYPHENYLBORONIC ACID plays a crucial role in the development of new cancer treatments by providing a starting material for the synthesis of these bioactive molecules.
Used in Cross-Coupling Reactions:
2-FORMYL-4,5-METHYLENEDIOXYPHENYLBORONIC ACID is used in Suzuki-Miyaura coupling reactions, a widely used method for the formation of carbon-carbon bonds in organic synthesis. This reaction allows for the creation of new molecular structures and the functionalization of existing compounds.
Used in Advanced Organic Synthesis:
2-FORMYL-4,5-METHYLENEDIOXYPHENYLBORONIC ACID is used in Suzuki and Negishi cross-coupling reactions, which are powerful tools for the formation of carbon-carbon and carbon-heteroatom bonds. These reactions are essential for the synthesis of complex organic molecules and the development of new materials and pharmaceuticals.

InChI:InChI=1/C8H7BO5/c10-3-5-1-7-8(14-4-13-7)2-6(5)9(11)12/h1-3,11-12H,4H2

Upstream product

• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 

Downstream Products

• 1149344-88-6 6-(2-acetylphenyl)benzo[d][1,3]dioxole-5-carbaldehyde 
• 1149344-98-8 6-(2-acetyl-5-fluorophenyl)benzo[d][1,3]dioxole-5-carbaldehyde 
• 880643-58-3 6-(cyclohex-1-en-1-yl)benzo[d][1,3]dioxole-5-carbaldehyde 
• 42123-15-9 6-<(3,4,5-trimethoxyphenyl)methyl>benzo-1,3-dioxole-5-carboxaldehyde 
• 1589546-26-8 C₃₀H₂₁O₄P 
• 1459238-37-9 6-(2-bromo-4-methoxyphenyl)benzo[d][1,3]dioxole-5-carbaldehyde 
• 61599-76-6 4,5-methylenedioxy-4',5',6'-trimethoxy-1,1'-biphenyl-2,2'-dicarboxaldehyde 
• 73252-65-0 methyl 2-formyl-4,5-methylenedioxy-4',5',6'-trimethoxy-1,1'-biphenyl-2'-carboxylate 
• 258283-80-6 6-[2,3,4-trimethoxy-6-(2-oxo-2,5-dihydro-furan-3-ylmethyl)-phenyl]-benzo[1,3]dioxole-5-carbaldehyde 

Relevant articles and documents

Discovery of 3-aryl substituted benzoxaboroles as broad-spectrum inhibitors of serine- and metallo-β-lactamases

The production of β-lactamases represents the main cause of resistance to clinically important β-lactam antibiotics. Boron containing compounds have been demonstrated as promising broad-spectrum β-lactamase inhibitors to combat β-lactam resistance. Here we report a series of 3-aryl substituted benzoxaborole derivatives, which manifested broad-spectrum inhibition to representative serine-β-lactamases (SBLs) and metallo-β-lactamases (MBLs). The most potent inhibitor 9f displayed an IC50 value of 86 nM to KPC-2 SBL and micromolar inhibitory activity towards other tested enzymes. Cell-based assays further revealed that 9f was able to significantly reduce the MICs of meropenem in clinically isolated KPC-2-producing bacterial strains and it showed no apparent toxicity in HEK293T cells.