| Identification | More | [Name]
Quinazoline | [CAS]
253-82-7 | [Synonyms]
1,3-BENZODIAZINE
PHENMIAZINE
QUINAZOLINE
1,3-Diazanaphthalene
4.5-Benzopyrimidine
Benzo(e)pyrimidine
Quinazoline (6CI,8CI,9CI)
benzo[a]pyrimidine
1,3-Benzodiazine, Benzopyrimidine
5,6-Benzopyrimidine
Quinazoline ,98%
Benzo[d]pyrimidine
Benzopyrimidine | [EINECS(EC#)]
205-965-3 | [Molecular Formula]
C8H6N2 | [MDL Number]
MFCD00006712 | [Molecular Weight]
130.15 | [MOL File]
253-82-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Beige to brownish crystalline powder | [Melting point ]
46-48 °C (lit.) | [Boiling point ]
243 °C (lit.) | [density ]
1.2002 (rough estimate) | [refractive index ]
1.6231 (estimate) | [Fp ]
224 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
H2O: freely soluble | [form ]
Crystalline Powder, Crystals and/or Chunks | [pka]
3.43(at 20℃) | [color ]
Yellow to beige to brownish | [Water Solubility ]
H2O: freely soluble
organic solvents: soluble | [Detection Methods]
GC,NMR | [Merck ]
14,8053 | [BRN ]
109370 | [InChI]
1S/C8H6N2/c1-2-4-8-7(3-1)5-9-6-10-8/h1-6H | [InChIKey]
JWVCLYRUEFBMGU-UHFFFAOYSA-N | [SMILES]
c1ccc2ncncc2c1 | [CAS DataBase Reference]
253-82-7(CAS DataBase Reference) | [NIST Chemistry Reference]
Quinazoline(253-82-7) | [EPA Substance Registry System]
253-82-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
5-Nitroisoquinoline-->Quinazoline, 1,4-dihydro--->4-Quinazolinecarboxamide-->4-Quinazolinemethanol, α-(4-methoxyphenyl)-α-methyl--->4-Chloroquinazoline-->ortho-Nitrobenzaldehydedimethylacetal-->2,3,4,5-Tetrahydro-1H-benzo[e][1,4]diazepine-->2(1H)-Quinazolinone (6CI,8CI,9CI)-->2,1-Benzisoxazole-->2-Aminobenzylamine | [Preparation Products]
7-chloro-1,3-dihydro-5-phenyl-2-oxo-2H-1,4-benzodiazepin-3-yl acetate-->Demoxepam-->4-Chloroquinazoline-->Bunazosin hydrochloride-->Quinapril-->Terazosin-->Doxazosin-->Alfuzosin hydrochloride-->Quinazolin-4-ylamine |
| Hazard Information | Back Directory | [Chemical Properties]
Beige to brownish crystalline powder | [Uses]
Quinazoline was used to study the electrochemical behaviour of quinazoline using modern polarographic and voltammetric methods. | [Uses]
Quinazoline was used to study the electrochemical behaviour of quinazoline using modern polarographic and voltammetric methods. It is the basic structural unit of pharmaceuticals and plays an important role in modern synthesis of antitumor drugs. | [Definition]
ChEBI: A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms. | [General Description]
Quinazolines has applications in medicinal chemistry due to their antibacterial, antifungal, anticonvulsant, anti-inflammatory and antitumor activities. It is the basic structural unit of pharmaceuticals and plays an important role in modern synthesis of antitumor drugs. | [Biochem/physiol Actions]
Genotoxicity of quinazoline was established by bacterial SOS Chromotest (Escherichia Coli). | [Synthesis]
The general method for the synthesis of quinazoline from 4-chloroquinazoline was as follows: first, the halogenated heterocycle (0.66 mmol) was dissolved in anhydrous THF (13.2 mL) and degassed by drumming argon gas for several minutes. Subsequently, PdCl2 (dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv), and NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were added sequentially. The reaction mixture was stirred at room temperature for an appropriate time under argon protection, after which it was post-treated according to standard methods. | [Purification Methods]
Purify quinazoline by passage through an activated alumina column in *C6H6 or pet ether (b 40-60o). Distil it under reduced pressure, sublime it under vacuum and crystallise it from pet ether. The picrate has m 188-189o (from MeOH). [Armarego J Appl Chem 11 70 1961, Armarego Quinazolines, Fused Pyrimidines Part I Brown Ed, Wiley-Interscience 1967, Brown Quinazolines Supplement I Taylor Ed, Wiley-Interscience 1996, ISBN 0-471-14565-3; for covalent hydration see Albert & Armarego Adv Heterocycl Chem 4 1 1965, Beilstein 23 H 175, 23 II 177, 23 III/IV 1221.] | [References]
[1] Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 191 - 209 |
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