75844-40-5

Basic information

• Product Name: 7-METHYLQUINAZOLIN-4(1H)-ONE
• Synonyms: 7-METHYLQUINAZOLIN-4(1H)-ONE;7-methylquinazolin-4(3H)-one;7-Methyl-4(3H)-quinazolinone;4(3H)-Quinazolinone, 7-methyl- >97%
• CAS NO: 75844-40-5
• Molecular Formula: C₉H₈N₂O
• Molecular Weight: 160.17
• Mol File: 75844-40-5.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 311.6°C at 760 mmHg
• Flash Point: 142.2°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 0.000559mmHg at 25°C
• Refractive Index: 1.644
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 7-METHYLQUINAZOLIN-4(1H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-METHYLQUINAZOLIN-4(1H)-ONE(75844-40-5)
• EPA Substance Registry System: 7-METHYLQUINAZOLIN-4(1H)-ONE(75844-40-5)

Safety Data

• Hazardous Substances Data: 75844-40-5(Hazardous Substances Data)

Usage

General Description

7-Methylquinazolin-4(1H)-one, also known as 7-methyl-1,2-dihydroquinazolin-4-one, is a heterocyclic compound with a quinazolinone core structure. It is a white crystalline solid with a molecular formula of C9H8N2O. This chemical is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It has also been studied for its potential use as an antitumor agent and for its antibacterial activity. 7-Methylquinazolin-4(1H)-one is classified as a heterocyclic compound, and its versatile nature makes it a valuable building block in organic synthesis.

InChI:InChI=1/C9H8N2O/c1-6-2-3-7-8(4-6)10-5-11-9(7)12/h2-5H,1H3,(H,10,11,12)

Upstream product

• 64-18-6 formic acid 
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• 77287-34-4 formamide 
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• 39549-79-6 2-amino-4-methylbenzamide 
• 67-56-1 methanol 
• 144-62-7 oxalic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 1829-21-6 4-methyl-2-iodobenzoic acid 
• 6313-33-3 formamidine hydrochloride 
• 50424-81-2 4-methyl-2-nitro-benzoyl chloride 
• 122-51-0 orthoformic acid triethyl ester 
• 65078-05-9 4-methyl-2-nitrobenzamide 
• 27329-27-7 4-methyl-2-nitrobenzoic acid 

Downstream Products

• 1449737-58-9 5-bromo-7-methyl-8-nitro-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine 
• 943606-89-1 7-methyl-N⁴-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine 
• 1093101-65-5 8-amino-7-methylquinazolin-4(3H)-one 
• 1093101-48-4 4-(8-amino-7-methylquinazolin-4-ylamino)benzonitrile 
• 1093101-47-3 4-(6-bromo-7-methyl-8-nitroquinazolin-4-ylamino)benzonitrile 
• 1093100-62-9 N₈-(3-(9H-purin-6-yI)pyridin-2-yI)-N₄-(4-chIorophenyl)-7-methylquinazoline-4,8-diamine 
• 1093100-51-6 4-(8-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile 
• 1093100-19-6 4-(8-(3-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile 
• 1093100-21-0 4-(8-(3-(9H-purin-6-yI)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile 
• 1093100-60-7 N₈-(3-(9H-purin-6-yI)pyridin-2-yl)-N₄-(3-ethynylphenyl)-7-methylquinazoline-4,8-diamine 
• 1093100-61-8 N₈-(3-(9H-purin-6-yl)pyridin-2-yl)-N₄-(4-(difluoromethoxy)phenyl)-7-methylquinazoline-4,8-diamine 
• 1093100-56-1 N₈-(3-(9H-purin-6-yl)pyridin-2-yl)-7-methyl-N₄-(3-(trifluoromethyl)phenyl)quinazolin-4,8-diamine 
• 1093100-20-9 4-(8-(3-(9-(4-methoxybenzyl)-9H-purin-6-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile 
• 1093101-62-2 4-(8-(3-(1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile 

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.

Design, synthesis, and evaluation of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides as antitumor agents

In our continuing search for novel small-molecule anticancer agents, we designed and synthesized a series of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides (5), focusing on the modification of substitution in the quinazolin-4(3H)-one moiety. The biological evaluation showed that all 13 designed and synthesized compounds displayed significant cytotoxicity against three human cancer cell lines (SW620, colon cancer; PC-3, prostate cancer; NCI-H23, lung cancer). The most potent compound 5l displayed cytotoxicity up to 213-fold more potent than 5-fluorouracil and 87-fold more potent than PAC-1, the first procaspase-activating compound. Structure–activity relationship analysis revealed that substitution of either electron-withdrawing or electron-releasing groups at positions 6 or 7 on the quinazolin-4(3H)-4-one moiety increased the cytotoxicity of the compounds, but substitution at position 6 seemed to be more favorable. In the caspase activation assay, compound 5l was found to activate the caspase activity by 291% in comparison to PAC-1, which was used as a control. Further docking simulation also revealed that this compound may be a potent allosteric inhibitor of procaspase-3 through chelation of the inhibitory zinc ion. Physicochemical and ADMET calculations for 5l provided useful information of its suitable absorption profile and some toxicological effects that need further optimization to be developed as a promising anticancer agent.

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.