943994-87-4

Basic information

• Product Name: 2H-1,4-Benzoxazin-3(4H)-one, 8-Methyl-6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-
• Synonyms: 2H-1,4-Benzoxazin-3(4H)-one, 8-Methyl-6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;8-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4H-1,4-benzoxazin-3-one;8-METHYL-6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE;(8-METHYL-3-OXO-3,4-DIHYDRO-2H-BENZO[B][1,4]OXAZIN-6-YL)BORONIC ACID PINACOL ESTER
• CAS NO: 943994-87-4
• Molecular Formula: C₁₅H₂₀BNO₄
• Molecular Weight: 289.1346
• Mol File: 943994-87-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-1,4-Benzoxazin-3(4H)-one, 8-Methyl-6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1,4-Benzoxazin-3(4H)-one, 8-Methyl-6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-(943994-87-4)
• EPA Substance Registry System: 2H-1,4-Benzoxazin-3(4H)-one, 8-Methyl-6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-(943994-87-4)

Safety Data

• Hazardous Substances Data: 943994-87-4(Hazardous Substances Data)

Usage

General Description

2H-1,4-Benzoxazin-3(4H)-one, 8-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, also known as DIMBOA, is a chemical compound that belongs to the benzoxazinoid family. It is a natural defense compound produced by various plants, including maize, wheat, and rye, to protect themselves against pests and pathogens. DIMBOA has been found to have antimicrobial, antioxidant, and allelopathic properties, making it attractive for potential applications in agriculture and medicine. Its unique structure and biological activities have garnered interest in the scientific community for further research into its potential uses and applications.

Upstream product

• 943994-74-9 methyl (4-bromo-2-methyl-6-nitrophenoxy)acetate 
• 20294-50-2 4-bromo-2-methyl-6-nitrophenol 
• 121564-97-4 6-bromo-8-methyl-2H-1,4-benzoxazin-3(4H)-one 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1221500-65-7 6-[5-(4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-yl]-8-methyl-2H-1,4-benzoxazin-3(4H)-one 
• 1221501-71-8 6-[1-(2,2-Difluoropropyl)-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl]-8-methyl-2H-1,4-benzoxazin-3(4H)-one 

Relevant articles and documents

Discovery of 6-[5-(4-fluorophenyl)-3-methyl-pyrazol-4-yl]-benzoxazin-3-one derivatives as novel selective nonsteroidal mineralocorticoid receptor antagonists

In the course of our study on selective nonsteroidal mineralocorticoid receptor (MR) antagonists, a series of novel benzoxazine derivatives possessing an azole ring as the core scaffold was designed for the purpose of attenuating the partial agonistic activity of the previously reported dihydropyrrol-2-one derivatives. Screening of alternative azole rings identified 1,3-dimethyl pyrazole 6a as a lead compound with reduced partial agonistic activity. Subsequent replacement of the 1-methyl group of the pyrazole ring with larger lipophilic side chains or polar side chains targeting Arg817 and Gln776 increased MR binding activity while maintaining the agonistic response at the lower level. Among these compounds, 6-[1-(2,2-difluoro-3-hydroxypropyl)-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl]-2H-1,4-benzoxazin-3(4H)-one (37a) showed highly potent in vitro activity, high selectivity versus other steroid hormone receptors, and good pharmacokinetic profiles. Oral administration of 37a in deoxycorticosterone acetate-salt hypertensive rats showed a significant blood pressure-lowering effect with no signs of antiandrogenic effects.