532-91-2

Basic information

• Product Name: 6-METHOXY-2-BENZOXAZOLINONE
• Synonyms: 6-METHOXY-2-BENZOXAZOLININE;6-METHOXY-2-BENZOXAZOLINONE;6-METHOXYBENZO[D]OXAZOL-2(3H)-ONE;2(3H)-Benzoxazolone, 6-methoxy-;2-Benzoxazolinone, 6-methoxy-;6-Mboa;6-Methoxy-1,3-benzoxazol-2(3H)-one;6-methoxy-2(3h)-benzoxazolon
• CAS NO: 532-91-2
• Molecular Formula: C₈H₇NO₃
• Molecular Weight: 165.15
• Product Categories: Heterocyclic Compounds;Oxazoles;Building Blocks;Heterocyclic Building Blocks;Oxazolines/Oxazolidines;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 532-91-2.mol
• Article Data: 20

Chemical Properties

• Melting Point: 151-156 °C(lit.)
• Boiling Point: 292.97°C (rough estimate)
• Flash Point: °C
• Appearance: light tan/
• Density: 1.3450 (rough estimate)
• Refractive Index: 1.5468 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Acetone, Dichloromethane, Methanol, Tetrahydrofuran
• PKA: 8.73±0.70(Predicted)
• BRN: 141041
• CAS DataBase Reference: 6-METHOXY-2-BENZOXAZOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXY-2-BENZOXAZOLINONE(532-91-2)
• EPA Substance Registry System: 6-METHOXY-2-BENZOXAZOLINONE(532-91-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: DM5275200
• Hazardous Substances Data: 532-91-2(Hazardous Substances Data)

Usage

Uses

6-Methoxybenzoxazolinone is an intermdiate in the synthesis of DIMBOA-4-O-β-D-glucuronide which is a metabolite of DIMBOA which acts as an antifungal and antialgal agent in crops. The benzoxazinone group within the structure allows for these effects.

Synthesis Reference(s)

Synthetic Communications, 23, p. 343, 1993 DOI: 10.1080/00397919308009786

General Description

6-Methoxy-2-benzoxazolinone (MBOA) is obtained by reacting 2-amino-5-methoxyphenol hydrochloride with urea. MOBA is a naturally occurring auxin-inhibiting substance present in maize shoots.

InChI:InChI=1/C8H7NO3/c1-11-5-2-3-6-7(4-5)12-8(10)9-6/h2-4H,1H3,(H,9,10)

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 40925-70-0 2-amino-5-methoxyphenol 
• 39547-15-4 1-amino-2-hydroxy-4-methoxybenzene hydrochloride 
• 57-13-6 urea 
• 75-44-5 phosgene 
• 52177-62-5 3-methoxyphenyl carbonochloridate 
• 150-19-6 O-methylresorcine 
• 13895-04-0 6-methoxybenzo[d]oxazole-2(3H)-thione 
• 55544-90-6 4-Hydroxy-2,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one 
• 13895-38-0 2-nitroso-5-methoxyphenol 
• 704-14-3 3-methoxy-6-nitro-phenol 
• 149182-67-2 2-hydroxy-4,7-dimethoxybenzoxazin-3-one 
• 15893-52-4 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one 
• 108-24-7 acetic anhydride 

Downstream Products

• 359434-29-0 6-hydroxy-3-methyl-2(3H)-benzoxazolone 
• 1750-47-6 5-chloro-6-methoxy-2-benzoxazolinone 

Relevant articles and documents

DECOMPOSITION IN APROTIC SOLVENTS OF 2,4-DIHYDROXY-7-METHOXY-1,4-BENZOXAZIN-3-ONE, A HYDROXAMIC ACID FROM CEREALS

The decomposition of the title compound (DIMBOA, 1) in aprotic solvents was analysed in terms of linear solvation energy relationships using donor numbers.The results indicate rate-limiting cyclic hemiacetal opening in low donor number solvents and rate-limiting isocyanate formation in high donor number solvents.The addition of H2O to DIMBOA decomposing in high donor number solvents had no effect upon the reaction rate, allowing one of the two proposed mechanisms to be rejected.

REACTION OF DIMBOA WITH AMINES

DIMBOA (2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one), a hydroxamic acid from cereals, reacted with primary amines to give an addition compound with two imino groups.Kinetic studies with DIMBOA and with the DIMBOA analogues 2,7-dimethoxy-1,4-benzoxazin-3-one and 2-hydroxy-7-methoxy-1,4-benzoxazin-3-one indicated that the reaction occurred through the intermediacy of the aldol tautomer of DIMBOA.The data is discussed in relation to the biological activyty of DIMBOA. Key Word Index - DIMBOA; hydroxamic acids; Gramineae; plant defence; anti inflamatory activity.

Synthesis of benzoxazolones from nitroarenes or aryl halides

Chemical equation presented A simple and effective method for the preparation of benzoxazolones from nitroarenes or aryl halides is described. Partial reduction of a nitro group in the presence of a chloroformate followed by a microwave-assisted rearrangement/ring closure sequence provides a convenient and practical procedure to prepare this important pharmacophore. Rearrangement precursors were also accessed from aryl halides through transitionmetal-catalyzed coupling.

Novel compounds for use in weight loss and appetite suppression in humans

Phenolic compounds with a phenolic molecule to which are covalently linked an oxygen-containing group, a nitrogen or another oxygen containing group, and a C1-C4 alkoxy group, obtainable from monocotyledonous plants, or by chemical synthesis, have been found to act as weight loss agents, appetite suppressants, mood enhancers and adjunctive therapy for arthritis, sleep apnea, fibromyalgia, diabetes and hyperglycemia. Additional chemical compounds of the present invention may include benzoxazinoids-cyclic hydroxyamic acids, lactams, and corresponding glucosides, which may serve as precursors to phenolic compounds. The phenolic compounds and precursors of phenolic compounds of the present invention, at concentrations suitable for human therapeutic use, may be obtained from monocotyledonous plants such as corn in their early growth states which are timely harvested for optimum yield.