72001-30-0

Basic information

• Product Name: 4-Acetoxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
• Synonyms: 4-Acetoxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
• CAS NO: 72001-30-0
• Molecular Formula: C₁₁H₁₁NO₅
• Molecular Weight: 237.2087
• Mol File: 72001-30-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 374.1°Cat760mmHg
• Flash Point: 180°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 8.58E-06mmHg at 25°C
• Refractive Index: 1.579
• CAS DataBase Reference: 4-Acetoxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Acetoxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one(72001-30-0)
• EPA Substance Registry System: 4-Acetoxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one(72001-30-0)

Safety Data

• Hazardous Substances Data: 72001-30-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H11NO5/c1-7(13)17-12-9-4-3-8(15-2)5-10(9)16-6-11(12)14/h3-5H,6H2,1-2H3

Upstream product

• 69884-05-5 4-hydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 704-14-3 3-methoxy-6-nitro-phenol 
• 157067-43-1 ethyl 5-methoxy-2-nitrophenoxyacetate 

Downstream Products

• 88171-01-1 (S)-2-tert-Butoxycarbonylamino-3-[1-(7-methoxy-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-4-oxo-cyclohexa-2,5-dienyl]-propionic acid ethyl ester 
• 88171-00-0 (S)-2-tert-Butoxycarbonylamino-3-[4-hydroxy-3-(7-methoxy-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-phenyl]-propionic acid ethyl ester 
• 6529-94-8 7-methoxy-2H-1,4-benzoxazin-3-one 
• 134934-26-2 7-methoxy-6-phenylthio-2H-1,4-benzoxazin-3(4H)-one 
• 72001-34-4 4-(2-hydroxy-4-methylphenyl)-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 
• 72001-33-3 4-(4-hydroxy-2-methylphenyl)-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 
• 72001-35-5 4-(2-hydroxy-6-methylphenyl)-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 
• 134934-24-0 4-(4-dimethylaminophenyl)-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 
• 134934-23-9 4-(2-hydroxy-5-methoxyphenyl)-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 
• 134934-25-1 7-methoxy-6-phenylamino-2H-1,4-benzoxazin-3(4H)-one 
• 103-84-4 Acetanilid 
• 72001-37-7 7-methoxy-4-(1-methyl-4-oxo-2,5-cyclohexadien-1-yl)-2H-1,4-benzoxazin-3(4H)-one 
• 72001-31-1 4-(4-hydroxyphenyl)-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 
• 134934-22-8 4-(2-hydroxyphenyl)-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 

Relevant articles and documents

Isolation and synthesis of allelochemicals from gramineae: Benzoxazinones and related compounds

Compounds with a (2H)-1,4-benzoxazin-3(4H)-one skeleton have attracted the attention of phytochemistry researchers since 2,4-dihydroxy-(2H)-1,4-benzoxazin- 3(4H)-one (DIBOA) and 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (DIMBOA) were isolated from plants belonging to the Poaceae family. These compounds exhibit interesting biological properties, such as phytotoxic, antimicrobial, antifeedant, antifungal, and insecticidal properties. These chemicals, in addition to a wide variety of related compounds involved in their metabolism, detoxification mechanisms, and degradation on crop soils and other systems, have high interest and in some cases potential agronomic utility. This paper presents a complete review of the methods employed for their synthetic obtention in addition to some of the authors' own contributions to their chemistry. The degradation and phytotoxicity experiments carried out in ongoing research into the potential agronomic utility of these compounds required large amounts of them, which were obtained from natural sources. This paper presents a modified methodology to access DIMBOA from Zea mays cv. Apache and to obtain 2-O-β-D-glucopyranosyl-2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA-Glc) and DIBOA from Secale cereale L. New synthetic methodologies were employed for the obtention of the lactams 2-hydroxy-(2H)-1,4-benzoxazin-3(4H)- one and 2-hydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one and the malonamic acids N-(2-hydroxyphenyl)malonamic acid and N-(2-hydroxy-7-methoxyphenyl)- malonamic acid. The aminophenoxazines 2-amino-7-methoxyphenoxazin-3-one and 2-acetamido-7-methoxyphenoxazin-3-one have been synthesized in the authors' laboratory by novel procedures. All of the methodologies employed allowed the desired compounds to be obtained in high yield and in an easy-to-scale manner.

A multi-centered electrophile formed from a unique bioactive cyclic hydroxamic acid, 4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one

4-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (HMBOA) is a compound of considerable interest because of its pharmacological, agrochemical, and antimicrobial properties. A plausible bioactive metabolite of HMBOA is 4-acetoxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (AMBOA). Electrophilic reactions of AMBOA with phenols, anilines, thiols, heteroaromatics, amino acid derivatives and nucleic acids were investigated in relation to the chemical mechanisms of the biological effects elicited by the compound. The results suggest that HMBOA acts as an alkylating agent of proteins and nucleic acids in vivo after metabolic O-acylation.