151480-73-8

Basic information

• Product Name: 3,4-dihydro-3-methyl-6-nitro-2H-1,3-benzoxazin-2-one
• Synonyms: 3,4-dihydro-3-methyl-6-nitro-2H-1,3-benzoxazin-2-one;2H-1,3-Benzoxazin-2-one,3,4-dihydro-3-Methyl-6-nitro-
• CAS NO: 151480-73-8
• Molecular Formula: C₉H₈N₂O₄
• Molecular Weight: 208.17
• Mol File: 151480-73-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 360.5°Cat760mmHg
• Flash Point: 171.8°C
• Appearance: /
• Density: 1.419g/cm³
• Vapor Pressure: 2.21E-05mmHg at 25°C
• Refractive Index: 1.602
• CAS DataBase Reference: 3,4-dihydro-3-methyl-6-nitro-2H-1,3-benzoxazin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dihydro-3-methyl-6-nitro-2H-1,3-benzoxazin-2-one(151480-73-8)
• EPA Substance Registry System: 3,4-dihydro-3-methyl-6-nitro-2H-1,3-benzoxazin-2-one(151480-73-8)

Safety Data

• Hazardous Substances Data: 151480-73-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H8N2O4/c1-10-5-6-4-7(11(13)14)2-3-8(6)15-9(10)12/h2-4H,5H2,1H3

Upstream product

• 1008-83-9 3-methyl-3,4-dihydro-2H-benzo[e][1,3]oxazin-2-one 
• 90-02-8 salicylaldehyde 
• 3117-65-5 2-(methyliminomethyl)phenol 
• 309965-27-3 4-Nitrophenyl N-(2-hydroxy-5-nitrobenzyl)-N-methylcarbamate 
• 75-44-5 phosgene 
• 35039-53-3 2-<(methylamino)methyl>-4-nitrophenol 
• 60399-02-2 N-methyl-2-hydroxybenzylamine 

Relevant articles and documents

The base-catalysed cyclisation of phenyl N-(2-hydroxybenzyl)-N-methylcarbamates is concerted

The kinetics of the cyclisation in aqueous solution of phenyl-(2-hydroxybenzyl) -N-methylcarbamates to 3-methyl-3,4-dihydrobenzol[e][1,3]oxazin-2-ones and phenolate ions fit the rate law: kobs = kc/(1 + [H3O+]/ ka) The values of kc and pKa fit Broonsted equations agains the pKa's of the corresponding free phenols but the system does not conform to the reactivity-selectiviy hypothesis. The values of the Broonsted parameters βY and βX vary as a function of Y and X according to the equations: βX = -0.179pKaHY + 0.87 βY = -0.179pKaHX + 2.30 The magnitude and sign of the Cordes-Thornton cross-interaction coefficient pXY(-0.179) rule out a stepwise mechanism involving a tetrahedral intermediate and is consistent with a concerted displacement mechanism. A similar concerted mechanism is proposed for the base-catalysed cyclisation of phenyl-N-(2-hydroxyphenyl)-N-methylcarbamate esters to benzoxazol-2-ones.

3,4-Dihydro-3-methyl-6-nitro-2H-1,3-benzoxazin-2-one, a Reagent for Labeling p-Nitrophenyl Esterases with a Chromophoric Reporter Group - Synthesis and Reaction with Chymotrypsin

We reported the synthesis of 3,4-dihydro-3-methyl-6-nitro-2H-1,3-benzoxazin-2-one (DMNB), a close structural anlogue of p-nitrophenyl dimethylcarbamate.DMNB is unstable in aqueous solution when exposed to light, but is stable in the dark.The compound reac