58421-80-0

Basic information

• Product Name: 4-CHLORO-8-METHYLQUINAZOLINE
• Synonyms: 4-CHLORO-8-METHYLQUINAZOLINE
• CAS NO: 58421-80-0
• Molecular Formula: C₉H₇ClN₂
• Molecular Weight: 178.62
• EINECS: 604-604-1
• Product Categories: blocks;Quinolines
• Mol File: 58421-80-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 129-130 °C
• Boiling Point: 298.2°C at 760 mmHg
• Flash Point: 162.3°C
• Appearance: /
• Density: 1.292
• Vapor Pressure: 0.00229mmHg at 25°C
• Refractive Index: 1.643
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.06±0.30(Predicted)
• CAS DataBase Reference: 4-CHLORO-8-METHYLQUINAZOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-8-METHYLQUINAZOLINE(58421-80-0)
• EPA Substance Registry System: 4-CHLORO-8-METHYLQUINAZOLINE(58421-80-0)

Safety Data

• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 58421-80-0(Hazardous Substances Data)

Usage

General Description

4-CHLORO-8-METHYLQUINAZOLINE is a chemical compound with the molecular formula C9H7ClN2. It is a chlorinated derivative of quinazoline and contains a methyl group at the 8th position. 4-CHLORO-8-METHYLQUINAZOLINE is used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds. It is also a valuable intermediate in the production of potential drug candidates and research chemicals. The chlorinated quinazoline moiety in 4-CHLORO-8-METHYLQUINAZOLINE confers unique properties that make it a versatile and valuable compound in organic synthesis. Further research and applications of this compound continue to expand its potential in the field of medicinal and chemical research.

InChI:InChI=1/C9H7ClN2/c1-6-3-2-4-7-8(6)11-5-12-9(7)10/h2-5H,1H3

Upstream product

• 19181-54-5 8-methylquinazolin-4(3H)-one 
• 4389-45-1 3-methylantranilic acid 
• 22223-49-0 methyl 2-amino-3-methylbenzoate 

Downstream Products

• 1445781-40-7 5-bromoquinazoline-8-carbonitrile 
• 7557-03-1 8-methylquinazoline 
• 1445781-75-8 N-[(S)-2-(8-cyano-quinazolin-5-ylamino)-2-(3-fluoro-phenyl)-ethyl]-N-methyl-4-nitro-benzenesulfonamide 
• 1445781-73-6 (S)-5-((1-(3-fluorophenyl)-2-(methylamino)ethyl)amino)quinazoline-8-carboxamide 
• 1442476-82-5 (E)-4-(2-(8-methylquinazolin-4-yloxy)phenyl)but-3-en-2-one 
• 1442476-46-1 (1E,4E)-1-(5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)-5-(2-(8-methylquinazolin-4-yloxy)phenyl)penta-1,4-dien-3-one 
• 1442476-52-9 (1E,4E)-1-(2,3-dichlorophenyl)-5-(2-(8-methylquinazolin-4-yloxy)phenyl)penta-1,4-dien-3-one 
• 1442476-54-1 (1E,4E)-1-(4-nitrophenyl)-5-(2-(8-methylquinazolin-4-yloxy)phenyl)penta-1,4-dien-3-one 
• 1442476-56-3 (1E,4E)-1-(2-methoxyphenyl)-5-(2-(8-methylquinazolin-4-yloxy)phenyl)penta-1,4-dien-3-one 
• 1442476-57-4 (1E,4E)-1-(3,4-dichlorophenyl)-5-(2-(8-methylquinazolin-4-yloxy)phenyl)penta-1,4-dien-3-one 
• 1442476-86-9 (E)-4-(4-((8-methylquinazolin-4-yl)oxy)phenyl)but-3-en-2-one 
• 1446863-22-4 8-(bromomethyl)-4-(4-(tert-butyl)phenyl)quinazoline 
• 1446863-20-2 4-(4-tert-butylphenyl)-8-methylquinazoline 
• 1446862-71-0 8-(aminomethyl)-4-[4-(t-butyl)phenyl]quinazoline 

Relevant articles and documents

Novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments: Design, synthesis and bioactivity

A series of novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether moieties were designed and synthesized. Their anticancer activities were evaluated by MTT assay, the results showed that most compounds exhibited extremely inhibitory effects against hepatoma SMMC-7721 cells. In particular, compounds Q2 and Q8 displayed the more potent inhibitory activity with IC50 values of 0.64 and 0.63 μM, which were better than that of gemcitabine (1.40 μM). Further mechanism studies indicated that compounds Q2, Q8, Q13 and Q19 could control the migration of SMMC-7721 cells effectively, and inhibit the proliferation of cancer cells by inhibiting the DNA replication. Western-blot results showed that compounds Q2 and Q8 induced irreversible apoptosis of SMMC-7721 cells by regulating the expression level of apoptose-related proteins. Those studies demonstrated that the penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments merited further research as potential anticancer agents.

Syntheses, antiviral activities and induced resistance mechanisms of novel quinazoline derivatives containing a dithioacetal moiety

A series of novel quinazoline derivatives containing a dithioacetal moiety were designed and synthesized, and their structures were characterized by 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, and high-resolution mass spectrometry. Bioassay results indicated that compound 4b exhibited remarkable protective activity against cucumber mosaic virus (CMV, EC50 = 248.6 μg/mL) and curative activity against potato virus Y (EC50 = 350.5 μg/mL), which were better than those of ningnanmycin (357.7 μg/mL and 493.7 μg/mL, respectively). Moreover, compound 4b could increase the chlorophyll content in plants, improve photosynthesis, and effectively induce tobacco anti-CMV activity.

Antimicrobial agents

The invention provides methods of treating a bacterial infection in a mammal comprising administering to the mammal a substituted bicyclic heteroaromatic ring compound of formula I: wherein two of X1 to X8 are N and the remaining of X1 to X8 are CH; or a pharmaceutically acceptable salt thereof, as well as novel compounds of formula I and salts thereof and pharmaceutical compositions comprising a compound of formula I or a pharmaceutically acceptable salt thereof.