Quinazoline

Quinazoline is an organic compound with the formula C8H6N2. It is an aromatic heterocycle with a bicyclic structure consisting of two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring. It is a light yellow crystalline solid that is soluble in water. Also known as 1,3-diazanaphthalene, quinazoline received its name from being an aza derivative of quinoline. Though the parent quinazoline molecule is rarely mentioned by itself in technical literature, substituted derivatives have been synthesized for medicinal purposes such as antimalarial and anticancer agents. Quinazoline is a planar molecule. It is isomeric with the other diazanaphthalenes of the benzodiazine subgroup: cinnoline, quinoxaline, and phthalazine. Over 200 biologically active quinazoline and quinoline alkaloids are identified.

Quinazoline
Names
Preferred IUPAC name
Quinazoline
Other names
1,3-diazanaphthalene

benzopyrimidine

phenmiazine

benzo-1,3-diazine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.424
EC Number
  • 205-965-3
UNII
  • InChI=1S/C8H6N2/c1-2-4-8-7(3-1)5-9-6-10-8/h1-6H Y
    Key: JWVCLYRUEFBMGU-UHFFFAOYSA-N Y
  • InChI=1/C8H6N2/c1-2-4-8-7(3-1)5-9-6-10-8/h1-6H
    Key: JWVCLYRUEFBMGU-UHFFFAOYAV
  • c1ccc2c(c1)cncn2
Properties
C8H6N2
Molar mass 130.150 g·mol−1
Appearance light yellow crystals
Density 1.351 g/cm3, solid
Melting point 48 °C (118 °F; 321 K)
Boiling point 243 °C (469 °F; 516 K)
Soluble
Acidity (pKa) 3.51
Structure
2.2 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Irritant
GHS labelling:
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 106 °C (223 °F; 379 K)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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