91634-12-7

Basic information

• Product Name: 2-VINYL-4-QUINAZOLINOL
• Synonyms: 2-VINYL-3H-QUINAZOLIN-4-ONE;2-VINYL-4-QUINAZOLINOL;4(3H)-Quinazolinone, 2-ethenyl-;2-vinylquinazolin-4(1H)-one
• CAS NO: 91634-12-7
• Molecular Formula: C₁₀H₈N₂O
• Molecular Weight: 172.18
• Mol File: 91634-12-7.mol

Chemical Properties

• Boiling Point: 315.4 °C at 760 mmHg
• Flash Point: 144.5 °C
• Appearance: /
• Density: 1.2 g/cm³
• Vapor Pressure: 0.000439mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 1.91±0.20(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 2-VINYL-4-QUINAZOLINOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-VINYL-4-QUINAZOLINOL(91634-12-7)
• EPA Substance Registry System: 2-VINYL-4-QUINAZOLINOL(91634-12-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 91634-12-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-VINYL-4-QUINAZOLINOL is used as a pharmaceutical agent for its anti-inflammatory properties, offering potential therapeutic benefits in treating various inflammatory conditions. Its ability to modulate inflammatory responses makes it a valuable compound for the development of new medications.
Used in Oncology Research:
In the field of oncology, 2-VINYL-4-QUINAZOLINOL is used as a potential anti-cancer agent, with research indicating its effectiveness against certain types of cancer. Its mechanism of action may involve the inhibition of cancer cell growth and the induction of apoptosis, making it a subject of interest for cancer treatment development.
Used in Organic Synthesis:
2-VINYL-4-QUINAZOLINOL is also used as a building block in the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of chemical entities, which can be further explored for their potential applications in different industries, including pharmaceuticals, materials science, and agrochemicals.
Overall, 2-VINYL-4-QUINAZOLINOL's diverse applications and potential for further development underscore its importance in the scientific community, with ongoing research aimed at unlocking its full potential in medicine and beyond.

InChI:InChI=1/C10H8N2O/c1-2-9-11-8-6-4-3-5-7(8)10(13)12-9/h2-6H,1H2,(H,11,12,13)

Upstream product

• 872998-62-4 C₈H₅BrN₂O 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 28144-70-9 anthranilic acid amide 
• 306996-53-2 2-(3-chloropropionylamino)-benzamide 

Downstream Products

• 4765-57-5 2-phenethylquinazolin-4-ol 
• 1414871-33-2 3-benzyl-2-ethenylquinazolin-4(3H)-one 

Relevant articles and documents

New isoxazolidine-conjugates of quinazolinones-synthesis, antiviral and cytostatic activity

A novel series of (3-diethoxyphosphoryl)isoxazolidines substituted at C5 with various quinazolinones have been synthesized by the 1,3-dipolar cycloaddition of N-methyl-C- (diethoxyphosphoryl)nitrone with N3-substitued 2-vinyl-3H-quinazolin-4-ones. All isoxazolidines were assessed for antiviral activity against a broad range of DNA and RNA viruses. Isoxazolidines trans-11f/cis-11f (90:10), trans-11h and trans-11i/cis-11i (97:3) showed weak activity (EC50 = 6.84, 15.29 and 9.44 μM) toward VZV (TK+ strain) which was only one order of magnitude lower than that of acyclovir used as a reference drug. Phosphonates trans-11b/cis-11b (90:10), trans-11c, trans-11e/cis-11e (90:10) and trans-11g appeared slightly active toward cytomegalovirus (EC50 = 27-45 μM). Compounds containing benzyl substituents at N3 in the quinazolinone skeleton exhibited slight antiproliferative activity towards the tested immortalized cells with IC50 in the 21-102 M range.

Superacid-promoted additions involving vinyl-substituted pyrimidines, quinoxalines, and quinazolines: Mechanisms correlated to charge distributions

The superacid-promoted reactions of vinyl-substituted N-heterocycles have been studied. Diprotonated pyrimidines, quinoxalines, and quinazolines exhibit an unusual regioelectronic effect that controls the type of addition reaction observed. Depending on the ring position of the vinyl substituent, either conjugate addition or Markovnikov addition occurs. The mode of addition has been shown to correlate well to NBO calculated charges.

Synthesis and reactions of some 2-Vinyl-3H-quinazolin-4-ones

A simple, high-yielding synthesis of 2-vinyl-3H-quinazolin-4-one, 2-(1-chlorovinyl)-3H-quinazolin-4-one and 2-(1-bromovinyl)-3H-quinazolin-4-one. The 2-vinylquinazolinones 11a and 14 participate readily in nucleophilic addition reactions. Treatment with both carbon and nitrogen nucleophiles results in a clean conversion into a variety of 2-substituted 3H-quinazolin-4-one derivatives. The 2-(1-halovinyl)-3H-quinazolin-4-ones 11b and 11c reacted with carbon nucleophiles to give several derivatives of 2-substituted 3H-quinazolin-4-one, such as dihydrofurancarboxylic ethyl ester 23. (C) 2000 Elsevier Science Ltd.