34923-95-0

Basic information

• Product Name: N-PHENYL-4-QUINAZOLINAMINE
• Synonyms: N-PHENYL-4-QUINAZOLINAMINE;4-(Phenylamino)quinazoline;4-Anilinoquinazoline;N-phenylquinazolin-4-amine
• CAS NO: 34923-95-0
• Molecular Formula: C₁₄H₁₁N₃
• Molecular Weight: 221.25724
• Mol File: 34923-95-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 386.1°Cat760mmHg
• Flash Point: 187.3°C
• Appearance: /
• Density: 1.256g/cm³
• Vapor Pressure: 3.64E-06mmHg at 25°C
• Refractive Index: 1.721
• CAS DataBase Reference: N-PHENYL-4-QUINAZOLINAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-PHENYL-4-QUINAZOLINAMINE(34923-95-0)
• EPA Substance Registry System: N-PHENYL-4-QUINAZOLINAMINE(34923-95-0)

Safety Data

• Hazardous Substances Data: 34923-95-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 39, p. 1785, 1998 DOI: 10.1016/S0040-4039(97)10864-4

InChI:InChI=1/C14H11N3/c1-2-6-11(7-3-1)17-14-12-8-4-5-9-13(12)15-10-16-14/h1-10H,(H,15,16,17)

Upstream product

• 5190-68-1 4-chloroquinazoline 
• 62-53-3 aniline 
• 64-18-6 formic acid 
• 951-48-4 2-amino-N′-phenylbenzamidine 
• 92165-07-6 N-(2-cyanophenyl)-N'-phenylthiourea 
• 35696-83-4 4-N-phenylaminoquinazoline-2-(1H)thione 
• 491-36-1 4-Hydroxyquinazoline 
• 897930-10-8 4-(1H-benzo[d][1,2,3]triazol-1-yloxy)quinazoline 
• 1885-29-6 anthranilic acid nitrile 
• 28144-70-9 anthranilic acid amide 
• 122-51-0 orthoformic acid triethyl ester 
• 149-73-5 trimethyl orthoformate 
• 1276665-99-6 C₈H₅Cl₅N₅OP₃ 
• 42366-35-8 hydroxyimino-N-phenylacetamide 

Relevant articles and documents

Synthesis of 4-arylaminoquinazolines via 2-amino-N-arylbenzamidines

A new synthesis of twelve 4-arylaminoquinazolines from 2-amino-N- arylbenzamidines and formic acid is described. The entering amidines were obtained in the reaction of anthranilonitrile with 50% molar excess of aromatic amines anhydrous aluminium chloride

Catalyst and solvent switched divergent C-H functionalization: Oxidative annulation of: N -aryl substituted quinazolin-4-amine with alkynes

The development of site-selective C-H functionalizations/annulations is one of the most challenging practices in synthetic organic chemistry particularly for substrates bearing several similarly reactive C-H bonds. Herein, we describe catalyst and solvent controlled ortho/peri site-selective oxidative annulation of C-H bonds of N-aryl substituted quinazolin-4-amines with internal alkynes. The ortho C-H selective annulation was observed using Pd-catalyst in DMF to give indole-quinazoline derivatives, while, Ru-catalyst in PEG-400 favoured the peri C-H bond annulation exclusively to furnish pyrido-quinazoline derivatives.

Facile and efficient synthesis and biological evaluation of 4-anilinoquinazoline derivatives as EGFR inhibitors

Series of 4-anilinoquinazoline derivatives were conveniently and efficiently synthesized and their antitumor activities were evaluated by MTT assay in three human cancer cell lines: H1975, HepG2 and SMMC-7721. New compounds 19a-19h were designed and synthesized to seek for powerful EGFR inhibitors and to explore whether methyl group at C-2 position of quinazoline ring has a positive effect on EGFR inhibition. All the compounds of 19a-19h were found potent against all three cell lines and five compounds (19c, 19d, and 19f-19h) were found more potent against H1975 than gefitinib. SAR studies revealed that methyl group at C-2 position of quinazoline ring could significantly improve the antitumor potency of 4-anilinoquinazolines. The same conclusion was also drawn according to the results of Western blotting analysis. Among all the tested compounds, 19g exhibited extremely potent against H1975 with an IC50 value of 0.11 μM, remarkably lower than that of gefitinib (1.23 μM). The results of western blotting analysis showed that compounds 19c and 19g could notably inhibit the expression of phosphorylated EGFR, especially 19g, almost inhibited completely.

One-pot multi component synthesis of 4-arylaminoquinazolines in the presence of sodium 30-tungstopentaphosphate

A new multi-component synthesis of 4-arylaminoquinazolines from the reaction of 2-aminobenzamide, orthoesters and substituted anilines in presence of catalytic amounts of sodium 30-tungstopentaphosphate, so-called Preyssler heteropolyacid, is reported. The effects of solvent, amount of catalyst and aniline and reaction time were studied. Optimum conditions for synthesis of 4-arylaminoquinazolines have been obtained.