15893-52-4

Basic information

• Product Name: 2,4-Dihydroxy-7-methoxy-2H,1,4-benzoxazin-3(4H)one
• Synonyms: 2,4-Dihydroxy-7-methoxy-2H,1,4-benzoxazin-3(4H)one;2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one;2,4-DIHYDROXY-7-METHOXY-1,4-BENZOXAZINONE;7,9-dihydroxy-3-methoxy-10-oxa-7-azabicyclo[4.4.0]deca-2,4,11-trien-8-one;2,4-Dihydroxy-7-methoxy-2,3-dihydro-4H-1,4-benzoxazine-3-one;2,4-Dihydroxy-7-methoxy-3,4-dihydro-2H-1,4-benzoxazine-3-one;7-Methoxy-2,4-dihydroxy-2H-1,4-benzooxazine-3(4H)-one;DIMBOA
• CAS NO: 15893-52-4
• Molecular Formula: C₉H₉NO₅
• Molecular Weight: 211.17
• Product Categories: Agro-Products, Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 15893-52-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 150-155 °C
• Boiling Point: 461.3 °C at 760 mmHg
• Flash Point: 232.8 °C
• Appearance: /
• Density: 1.589 g/cm³
• Vapor Pressure: 2.64E-09mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 7.59±0.40(Predicted)
• CAS DataBase Reference: 2,4-Dihydroxy-7-methoxy-2H,1,4-benzoxazin-3(4H)one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dihydroxy-7-methoxy-2H,1,4-benzoxazin-3(4H)one(15893-52-4)
• EPA Substance Registry System: 2,4-Dihydroxy-7-methoxy-2H,1,4-benzoxazin-3(4H)one(15893-52-4)

Safety Data

• Hazardous Substances Data: 15893-52-4(Hazardous Substances Data)

Usage

Description

2,4-Dihydroxy-7-methoxy-2H,1,4-benzoxazin-3(4H)one, also known as DIMBOA, is a lactol derivative of DIBOA in which the hydrogen at position 7 is replaced by a methoxy group. It is a naturally occurring compound that has been isolated from maize plants and is characterized by its benzoxazinone group within its structure.

Uses

Used in Agricultural Industry:
2,4-Dihydroxy-7-methoxy-2H,1,4-benzoxazin-3(4H)one is used as an antifungal and antialgal agent for crops. The presence of the benzoxazinone group within its structure allows it to effectively protect plants from fungal and algal infections, thereby enhancing crop health and yield.
It is important to note that the provided materials do not mention any other specific applications for 2,4-Dihydroxy-7-methoxy-2H,1,4-benzoxazin-3(4H)one in different industries. However, based on its antifungal and antialgal properties, it can be inferred that DIMBOA may have potential applications in other industries where these properties are beneficial, such as in the development of natural preservatives or in the production of bio-based materials with enhanced resistance to fungal and algal growth.

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 1788, 1991 DOI: 10.1021/jo00005a025

InChI:InChI=1/C9H9NO5/c1-14-5-2-3-6-7(4-5)15-9(12)8(11)10(6)13/h2-4,9,12-13H,1H3

Upstream product

• 157067-47-5 2,2-Di-tert-butyl-7-methoxy-1,3,5-trioxa-9b-aza-2-sila-cyclopenta[a]naphthalene 
• 69884-05-5 4-hydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one 
• 1026806-90-5 Methoxymethoxy-(5-methoxy-2-nitro-phenoxy)-acetic acid isopropyl ester 
• 56536-70-0 potassium 5-methoxy-2-nitrophenoxide 
• 55544-88-2 methyl α-(5-methoxy-2-nitrophenoxy)-α-methoxyacetate 
• 18607-79-9 2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3-one 
• 157067-49-7 2,2-Di-tert-butyl-7-methoxy-1,3,4,5-tetraoxa-9b-aza-2-sila-cyclopenta[a]cyclopropa[b]naphthalene 
• 151253-61-1 4-hydroxy-7-methoxy-2,3-dioxo-1,4-benzoxazine 
• 55544-90-6 4-Hydroxy-2,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one 
• 103150-46-5 N-(2-hydroxy-4-methoxy-phenyl)-glyoxylohydroxamic acid 
• 157067-43-1 ethyl 5-methoxy-2-nitrophenoxyacetate 

Downstream Products

• 532-91-2 coixol 
• 17359-53-4 2-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 
• 103150-46-5 N-(2-hydroxy-4-methoxy-phenyl)-glyoxylohydroxamic acid 
• 85758-42-5 2-Ethylsulfanyl-2-hydroxy-N-(2-hydroxy-4-methoxy-phenyl)-acetamide 
• 188358-90-9 2-benzyloxy-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 
• 18607-79-9 2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3-one 
• 188358-92-1 2-benzyloxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one 
• 62655-08-7 3-acetyl-6-methoxy-2-benzoxazolinone 

Relevant articles and documents

Completion of the spectroscopical data for the synthesis of DIMBOA

Cyclic hydroxamic acids like 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin- 3(4H)-one (DIMBOA) and 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one (DIBOA) are found in several plants playing an important role in the defense-system of plants against a variety of enemies. To investigate new mechanism and effects we synthesized the molecules using known synthetic pathways. Since the chemical data of DIMBOA are not complete or even false, we decided to publish the missing ones in this journal. O?sterreichische Apotheker-Verlagsgesellschaft m. b. H.

An improved synthesis of cyclic hydroxamic acids from Gramineae

The boron trichloride sensitive methoxymethyl (MOM) protecting group has been used to efficiently synthesize polymethoxylated derivatives of the benzoxazinone family of cyclic hydroxamic acids. The MOM group allows the unveiling of the hemiacetal at C-2 of these compounds without demethylating ring methoxy substituents, resulting in greatly increased yields.

α-Hydroxylation of Cyclic Hydroxamic Acids by Peroxide Oxidation: A Novel Approach to Allelochemicals from Graminae

Naturally occurring hemiacetals DIBOA and DIMBOA were synthesized by the first α-hydroxylation of N-hydroxylactams via m-chloroperbenzoic acid oxidation of corresponding cyclosilyl enol ethers.