111478-49-0

Basic information

• Product Name: 2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE
• Synonyms: 4H-1-Benzopyran-4-one, 2,3-dihydro-2,2-dimethyl-6-nitro-;2,2-diMethyl-6-nitro-3,4-dihydro-2H-1-benzopyran-4-one;2,3-Dihydro-2,2-dimethyl-6-nitro-4H-1-benzopyran-4-one
• CAS NO: 111478-49-0
• Molecular Formula: C11H11NO4
• Molecular Weight: 221.21
• Mol File: 111478-49-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 373℃
• Boiling Point: 365.9°Cat760mmHg
• Flash Point: 171.1°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 1.52E-05mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE(111478-49-0)
• EPA Substance Registry System: 2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE(111478-49-0)

Safety Data

• Hazardous Substances Data: 111478-49-0(Hazardous Substances Data)

Usage

General Description

2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE is a chemical compound with the molecular formula C13H11NO5. It is a nitro-substituted chromanone that is commonly used in organic synthesis and pharmaceutical research. 2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE is known for its potential pharmacological activities, including antioxidant, anti-inflammatory, and neuroprotective properties. It has also been studied for its potential use in the treatment of various diseases, including cancer and neurodegenerative disorders. Additionally, 2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE has shown promising results in preclinical studies, making it a subject of interest for further research and development in the field of medicinal chemistry.

InChI:InChI=1/C11H11NO4/c1-11(2)6-9(13)8-5-7(12(14)15)3-4-10(8)16-11/h3-5H,6H2,1-2H3

Upstream product

• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 100-02-7 4-nitro-phenol 
• 3780-33-4 2,3-dihydro-2,2-dimethylbenzo[b]pyran-4-one 
• 1450-76-6 1-(2-hydroxy-5-nitrophenyl)ethanone 
• 67-64-1 acetone 

Downstream Products

• 33143-28-1 6-nitro-2,2-dimethyl chromene 
• 135082-85-8 2,2-dimethyl-2H-1-benzopyran-6-amine 

Relevant articles and documents

2,2-Dimethyl-6-nitro-3,4-dihydro-2H-benzo[b]pyran-4-one O-benzoyloxime

The title compound, C18H16N2O5, has a pyran ring in a half-chair conformation fused to a benzene ring. The substituent groups at C3 and C5 are approximately coplanar with the benzopyran nucleus, with dihedral angles of 8.5 (5) and 4.2 (5)°, respectively. The benzoyloxy carbonyl group and the benzene ring of the benzopyran moiety both adopt a cis configuration.

Identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives as potassium channel activators and anti-inflammatory agents

The present study described the design, synthesis and identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives. Their biological activity was tested for KATP channel opener as antihypertensives, COX-1 and COX-2 activity. The results were compared with the activity of cromakalim, ibuprofen and celecoxib. The study aimed at exploring the influence of introduction of a benzoxazine substituent at position 6 of various derivatives of benzopyrans in order to improve biological activity. Several compounds were found to be equipotent or even more potent than cromakalim. Out of these nitro-substituted benzopyrans, nitro substitution at benzoxazino group possessed potent antihypertensive activity in the R/S isomers. With amino derivatives, activity remains constant when compared with standard cromakalim. Similarly, compounds 17b, 17c, 17e and 17h have exhibited around 40 % inhibition of COX-1 as compared to the inhibition of COX-2. Only two compounds 17g and 17i exhibited effective inhibition more than 50 % of COX-2 compared with the inhibition of COX-1 at a concentration of 0.3 mg/ml.

Expeditious photochemical reaction toward the preparation of substituted chroman-4-ones

A facile photochemical preparation of 5-, 6-, and 7-substituted chroman-4-ones from aryl 3-methyl-2-butenoate esters is described. The two-phase base-catalyzed method relies upon two consecutive processes in one-pot reaction through a photo-Fries rearrangement and a based-catalyzed intramolecular oxa-Michael addition to afford the desired products.