19181-64-7

Basic information

• Product Name: 6-METHOXYQUINAZOLIN-4-OL
• Synonyms: 6-METHOXYQUINAZOLIN-4-OL;6-METHOXY-4(1H)-QUINAZOLINONE;6-Methoxy-4(3H)-quinazolinone;6-Methoxyquinazolin-4(3H)-one
• CAS NO: 19181-64-7
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• EINECS: 242-961-0
• Mol File: 19181-64-7.mol

Chemical Properties

• Melting Point: 242-243℃
• Boiling Point: 361.758 °C at 760 mmHg
• Flash Point: 172.586 °C
• Appearance: /
• Density: 1.32
• Vapor Pressure: 0.0269mmHg at 25°C
• Refractive Index: 1.544
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 6-METHOXYQUINAZOLIN-4-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXYQUINAZOLIN-4-OL(19181-64-7)
• EPA Substance Registry System: 6-METHOXYQUINAZOLIN-4-OL(19181-64-7)

Safety Data

• Hazardous Substances Data: 19181-64-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Methoxyquinazolin-4-ol is used as a potential drug candidate for the development of pharmaceuticals aimed at treating various medical conditions. Its unique chemical structure and properties suggest that it may have therapeutic applications, although the exact uses and mechanisms of action would need to be determined through additional research.
Used in Drug Development Research:
In the field of drug development, 6-Methoxyquinazolin-4-ol is utilized as a subject of research to investigate its potential as a lead compound for the creation of new medications. Its chemical properties and interactions with biological systems could provide insights into its efficacy and safety, guiding the design of future therapeutic agents.

InChI:InChI=1/C5H6O3/c1-3-5(7)4(6)2-8-3/h7H,2H2,1H3

Upstream product

• 77287-34-4 formamide 
• 6705-03-9 2-Amino-5-methoxybenzoic acid 
• 394-31-0 2-amino-5-hydroxybenzoic acid 
• 1882-69-5 5-methoxy-2-nitro-benzoic acid 
• 1882-71-9 2-amino-5-methoxybenzamide 
• 3473-63-0 formamidine acetic acid 
• 6313-33-3 formamidine hydrochloride 
• 22921-68-2 2-bromo-5-methoxy-benzoic acid 
• 54413-93-3 2-iodo-5-methoxybenzoic acid 
• 463-52-5 formamidine 
• 68-12-2 N,N-dimethyl-formamide 
• 67-56-1 methanol 
• 1882-72-0 methyl 2-amino-5-hydroxybenzoate 
• 2475-80-1 methyl 2-amino-5-methoxybenzoate 

Downstream Products

• 50424-28-7 4-chloro-6-methoxyquinazoline 
• 1613479-55-2 C₁₅H₁₀F₂N₂O₂ 

Relevant articles and documents

Photo-Triggered Self-Induced Homolytic Dechlorinative Sulfonylation/Cyclization of Unactivated Alkenes: Synthesis of Quinazolinones Containing a Sulfonyl Group

A self-photocatalyzed sulfonylation/cyclization of quinazolinones containing unactivated alkenes with various sulfonyl chlorides was developed. The protocol provides access to sulfonyl radicals via energy transfer from the quinazolinone skeleton to the sulfonyl chloride. Notably, the transformations proceeded without any external photocatalysts, additives, or oxidants, providing an alternative method for fabricating sulfonylated compounds.

Electrosynthesis of CF3-Substituted Polycyclic Quinazolinones via Cascade Trifluoromethylation/Cyclization of Unactivated Alkene

An atom and step economy cascade trifluoromethylation/cyclization of unactivated alkene with Langlois reagent as a CF3 source is described. A variety of polycyclic quinazolinones were successfully synthesized in 52–81% yields under transition metal- and oxidant-free conditions. The Langlois reagent used in this strategy as a CF3 reagent possesses the advantages of bench-stablity, cost-effectivity and high-efficiency. Additionally, gram-scale reaction, broad substrate scope and good functional group tolerance demonstrated the synthetic usefulness of this protocol.

Visible-Light Photosynthesis of CHF2/CClF2/CBrF2-Substituted Ring-fused Quinazolinones in Dimethyl Carbonate

With eco-friendly and sustainable CO2-derived dimethyl carbonate as the sole solvent, the visible-light-induced cascade radical reactions have been established as a green and efficient tool for constructing various CHF2/CClF2/CBrF2-substituted ring-fused quinazolinones.

Self-catalyzed phototandem perfluoroalkylation/cyclization of unactivated alkenes: Synthesis of perfluoroalkyl-substituted quinazolinones

A novel visible-light-induced radical tandem trifluoromethylation/cyclization of unactivated alkenes with sodium perfluoroalkanesulfinates (Rf = CF3, C3F7, C4F9, C6F13, C8F17) under air atmosphere has been developed. A range of quinazolinones containing unactivated alkene moiety and sodium perfluoroalkanesulfinates were compatible with this transformation, leading to a variety of perfluoroalkyl-substituted quinazoline alkaloids. Remarkably, the experiment can be carried out without any metal catalyst, strong oxidant, or external photosensitizer.

Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives

A novel and green strategy for the synthesis of acylated quinazolinone derivativesviaphoto-induced decarboxylative cascade radical acylation/cyclization of quinazolinone bearing unactivated alkenes has been developed. The protocol provides a novel route to access acyl radicals from α-keto acids through a self-catalyzed energy transfer process. Most importantly, the reaction proceeded smoothly without any external photocatalyst, additive or oxidant, and could be easily scaled-up in flow conditions with sunlight irradiation.

Photo-triggered self-catalyzed fluoroalkylation/cyclization of unactivated alkenes: Synthesis of quinazolinones containing the CF2R group

A novel photo-triggered self-catalyzed fluoroalkylation/cyclization of quinazolinones containing unactivated alkenes with various fluoroalkyl bromides has been developed. This transformation exhibits excellent substrate generality with respect to both the coupling partners. Of note is that this is the first example describing the Csp3-Br bond homolysis of alkyl bromides via a substrate (quinazolinones) induced energy transfer process. Additionally, the mild conditions, tolerance to a wide range of functional groups and operational simplicity make this protocol practical for the synthesis of fluorine-containing ring-fused quinazolinones. This journal is

Method for photocatalytic synthesis of quinazolinone compound in aqueous phase (by machine translation)

The method comprises the following steps: taking the compound of the formula (I) and the compound of the formula (II) as a solvent, adding a photocatalyst and a phase transfer catalyst to obtain the quinazolinone compound (III) under the condition of alkali and visible light. Compared with the prior art, the method not only can be applied to a large amount of functional groups, has high yield, few byproducts, and is simple and safe to operate, low in cost and environment-friendly. Wherein R is hydrogen or R1 Is H, C1 - C4 alkoxy, halogen or nitro; R2 Is H, substituted or unsubstituted phenyl, 2 - pyridyl or 2 - thienyl; the substituted phenyl is phenyl substituted by amino, nitro, C1 - C4 alkyl or C1 - C4 alkoxy. (by machine translation)

Method for synthesizing quinazolinone compound by photo-catalyzing alcohol oxidation in water phase

The invention discloses a method for synthesizing a quinazolinone compound by photo-catalyzing alcohol oxidation in a water phase, which comprises the following steps: by taking a compound shown as aformula (I) and a compound shown as a formula (II) as raw materials and water as a solvent, adding a visible light catalyst, and reacting under the conditions of alkali and visible light to obtain a quinazolinone compound (III). The method for preparing the quinazolinone compound is environmentally friendly, easy and convenient to operate, safe, cheap and efficient. Compared with the prior art, the method is applicable to a large number of functional groups, high in yield, few in byproducts, simple and safe to operate, low in cost and environment-friendly; wherein R1 is H, C1-C4 alkoxy, halogen or nitro; and R2 is H, substituted or unsubstituted phenyl, 2-pyridyl, 2-thienyl or 5-methylfuryl.

Imidazolium chloride as an additive for synthesis of 4(3H)-quinazolinones using anthranilamides and DMF derivatives

Imidazolium chloride as an environmentally benign additive efficiently facilitates construction of 4(3H)-quinazolinones using anthranilamides and DMF derivatives. A series of 4(3H)-quinazolinones were prepared in moderate to excellent yields without conventional oxidants, metal catalysts and corrosive acids or other additives.

IDENTIFICATION AND USE OF ERK5 INHIBITORS

The present invention covers heterocyclic compounds of general formula (I) in which T, U, Y, Z, R1 and R3 are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of cancer disorders, as a sole agent or in combination with other active ingredients.