253-82-7

Basic information

• Product Name: Quinazoline
• Synonyms: 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%
• CAS NO: 253-82-7
• Molecular Formula: C₈H₆N₂
• Molecular Weight: 130.15
• EINECS: 205-965-3
• Product Categories: PYRIMIDINE
• Mol File: 253-82-7.mol
• Article Data: 34

Chemical Properties

• Melting Point: 46-48 °C(lit.)
• Boiling Point: 243 °C(lit.)
• Flash Point: 224 °F
• Appearance: Yellow to beige to brownish/Crystalline Powder, Crystals and/or Chunks
• Density: 1.2002 (rough estimate)
• Vapor Pressure: 0.0545mmHg at 25°C
• Refractive Index: 1.6231 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: H2O: freely soluble
• PKA: 3.43(at 20℃)
• Merck: 14,8053
• BRN: 109370
• CAS DataBase Reference: Quinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: Quinazoline(253-82-7)
• EPA Substance Registry System: Quinazoline(253-82-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26-23
• WGK Germany: 3
• Hazardous Substances Data: 253-82-7(Hazardous Substances Data)

Usage

Chemical Properties

Beige to brownish crystalline powder

Uses

Different sources of media describe the Uses of 253-82-7 differently. You can refer to the following data:
1. 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.
2. Quinazoline was used to study the electrochemical behaviour of quinazoline using modern polarographic and voltammetric methods.

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ChEBI: A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.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).

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.]

InChI:InChI=1/C8H6N2/c1-2-4-8-7(3-1)5-9-6-10-8/h1-6H

Upstream product

• 631-61-8 ammonium acetate 
• 529-23-7 o-aminobenzaldehyde 
• 55326-11-9 2-anisyl-4-quinazolinyl ketone 
• 20627-73-0 1-(dimethoxymethyl)-2-nitrobenzene 
• 77287-34-4 formamide 
• 552-89-6 2-nitro-benzaldehyde 
• 151-50-8 potassium cyanide 
• 187336-04-5 4-(α-benzyl-α-hydroxybenzyl)quinazoline 
• 1904-64-9 3,4-dihydroquinazoline 
• 64-19-7 acetic acid 
• 91085-79-9 N,N'-(2-nitro-benzylidene)-bis-formamide 
• 24313-88-0 3,4,5-Trimethoxyaniline 
• 71-36-3 butan-1-ol 
• 271-58-9 anthranil 

Downstream Products

• 1899-48-5 2,4-diaminoquinazoline 
• 32907-43-0 quinazoline-N-oxide 
• 491-36-1 4-Hydroxyquinazoline 
• 1904-65-0 1,2,3,4-tetrahydroquinazoline 
• 7556-95-8 6-nitro-quinazoline 
• 2217-31-4 3-ethyl-2(1H)-quinolinone 
• 5661-06-3 2,3-dihydro-1H-cyclopenta[b]quinoline 
• 104548-11-0 4-cyano-3-(2-chloromethylbenzoyl)-3,4-dihydroquinazoline 
• 126994-63-6 1,3-di(o-chloromethylbenzoyl)-2,4-dicyano-1,2,3,4-tetrahydroquinazoline 
• 76051-73-5 4-cyano-3,4-dihydroquinazoline hydrochloride 
• 76051-72-4 2,4-dicyano-1,3-dibenzoyl-1,2,3,4-tetrahydroquinazoline 
• 98512-42-6 4-(3-phenylpropyl)quinazoline 
• 59-31-4 2-quinolone 
• 94447-50-4 3-acetyl-3,4-dihydro-4-hydroxyquinazoline 

Relevant articles and documents

Hydrogenation/dehydrogenation of N-heterocycles catalyzed by ruthenium complexes based on multimodal proton-responsive CNN(H) pincer ligands

Ru complexes based on lutidine-derived pincer CNN(H) ligands having secondary amine side donors are efficient precatalysts in the hydrogenation and dehydrogenation of N-heterocycles. Reaction of a Ru-CNN(H) complex with an excess of base produces the formation of a Ru(0) derivative, which is observed under catalytic conditions.

Gold(0) catalyzed dehydrogenation of N-heterocycles

Gold nanoclusters are good catalyst precursors for the catalytic dehydrogenation of indolines, tetrahydroquinazolines, and related N-heterocycles. The catalytically active species is presumably Au(0) nanoparticles.

Divergent Synthesis of Quinazolines Using Organocatalytic Domino Strategies under Aerobic Conditions

An easy and efficient organocatalytic approach to the synthesis of 2-substituted quinazolines is described based on the reaction between 2-aminobenzylamines and aldehydes or alcohols or amines. Three organocatalytic platforms were investigated, using 3-nitropyridine, pyridine N-oxide, and vitamin B3. Having established the new catalytic systems, the tandem transformations of 2-aminobenzylamines to give substituted quinazolines were achieved in excellent yields and with a broad substrate scope, with no formation of toxic side-products. The investigated conditions are not restricted to the use of aldehydes; the protocol also works well with alcohols or amines as substrates. These are oxidized in situ to the corresponding aldehydes to achieve the successful transformation. A mechanistic proposal has been drawn up based on control experiments. We found that under aerobic conditions, catalytic amounts of H2O2 can be generated; this plays a key role in the efficacy of the described approach. The green chemistry metrics of the developed method are also presented. The E factor of 8.18 mg/1 mg demonstrates that the reported method is an excellent complement to previous protocols.