7501-38-4

Basic information

• Product Name: 2-(2-nitrophenyl)-4H-3,1-benzoxazin-4-one
• Synonyms: 4H-3,1-benzoxazin-4-one, 2-(2-nitrophenyl)-
• CAS NO: 7501-38-4
• Molecular Formula: C₁₄H₈N₂O₄
• Molecular Weight: 268.2243
• Mol File: 7501-38-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 429.4°C at 760 mmHg
• Flash Point: 213.5°C
• Density: 1.43g/cm³
• Vapor Pressure: 1.4E-07mmHg at 25°C
• Refractive Index: 1.679
• CAS DataBase Reference: 2-(2-nitrophenyl)-4H-3,1-benzoxazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-nitrophenyl)-4H-3,1-benzoxazin-4-one(7501-38-4)
• EPA Substance Registry System: 2-(2-nitrophenyl)-4H-3,1-benzoxazin-4-one(7501-38-4)

Safety Data

• Hazardous Substances Data: 7501-38-4(Hazardous Substances Data)

Usage

Chemical class

Benzoxazinoids

Occurrence

Found in various plants, including cereals (wheat, rye, and maize), grasses, and weeds

Allelopathic properties

Inhibits the growth of competing plants by releasing toxic substances into the soil

Potential uses

Natural herbicide, defense compound against herbivores, antimicrobial and insecticidal activities

Derivatives

Synthesized for potential pharmacological and agricultural applications

Upstream product

• 68506-37-6 2-(2-nitrobenzamido)benzoic acid 
• 108-24-7 acetic anhydride 
• 118-92-3 anthranilic acid 
• 610-14-0 2-nitrobenzyl chloride 
• 552-16-9 ortho-nitrobenzoic acid 
• 37960-65-9 potassium anthranilate 
• 72367-10-3 2-(2-nitrobenzoylamino)benzoic acid methyl ester 
• 134-20-3 2-carbomethoxyaniline 
• 88116-43-2 N-(2'-formylphenyl)-2-nitrobenzamide 

Downstream Products

• 316142-99-1 2-nitro-N-(2-(phenylcarbamoyl)phenyl)benzamide 
• 67718-36-9 N-[2-(aminocarbonyl)phenyl]-2-nitrobenzamide 
• 7265-24-9 2-(2'-amino-phenyl)-benzo[d][1,3]oxazin-4-one 
• 68506-37-6 2-(2-nitrobenzamido)benzoic acid 
• 96609-67-5 [2-(2-Nitro-benzoylamino)-benzoylamino]-acetic acid benzyl ester 
• 54987-33-6 3-amino-2-(2'-aminophenyl)-quinazolin-4(3H)-one 
• 612-34-0 N-anthraniloyl-anthranilic acid 
• 432543-93-6 2-(2-nitrophenyl)-3-hydroxy-quinazoline-4(3H)-one 
• 301152-31-8 2-(2-aminophenyl)-3-hydroxyquinazolin-4-(3H)-one 
• 96609-68-6 [2-(2-Amino-benzoylamino)-benzoylamino]-acetic acid 
• 96609-69-7 2-[2-(tert-butyloxycarbonyl)aminoethanoyl]aminophenyl-3,1-benzoxazin-4-one 
• 96609-71-1 2-[2-aminoethanoyl]aminophenyl-3,1-benzoxazin-4-one hydrochloride 
• 96609-72-2 (S)-2-Amino-N-[2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)-phenyl]-propionamide; hydrochloride 
• 2929-93-3 p-tolylmethylenediacetate 

Relevant articles and documents

Structural Insights into the Hydrogen-Bonding and Folding Pattern in Ant-Ant-Pro-Gly Tetrapeptides

In this paper, we provide structural insights into the hydrogen-bonding and folding pattern in Ant-Ant-Pro-Gly tetrapeptides (Ant: anthranilic acid; Pro: proline; and Gly: glycine). Comparison of the C-terminal esters and their amide analogs revealed strikingly different H-bonding networks. Whereas the ester analogs displayed an open structure without terminal H-bonding interactions, the amide analogs showed a completely folded structure. Structural details were revealed by using a combination of X-ray crystal structure studies and NOE-based molecular dynamics (MD) simulation studies.

TBHP/CoCl2-mediated intramolecular oxidative cyclization of N-(2-formylphenyl)amides: An approach to the construction of 4H-3,1-benzoxazin-4-ones

The intramolecular oxidative cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as an oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives and features readily available starting materials and mild reaction conditions. The intramolecular cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as the oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives.

Synthesis of 2-Aryl-4H-3,1-Benzoxazin-4-ones: A Class of α-Chymotrypsin Inhibitors

Twenty one derivatives of 2-aryl-4H-3,1-benzoxazin-4-one were synthesized and their potential therapeutically significance and structureactivity relationship were tested against α-chymotrypsin. Majority of synthesized compounds showed significant in vitro α-chymotrypsin inhibitory properties having IC50values in the range of 5.42 ± 1.66 - 41.27 ± 1.33 μM, whereas standard inhibitor chymostatin have IC50 value 7.13 ± 1.06 μM. In the present series compounds 2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one (3h), 2-(2-bromophenyl)-4H-3,1- benzoxazin-4-one (3n) and 2-(1-naphthyl)-4H-3, 1-benzoxazin-4-one (3t) with IC50values 7.22 ± 0.75, 6.99 ± 0.29 and 5.42 ± 1.66 μM, respectively were found to be most active members of series, even better than standard inhibitor a-chymostatin.