5152-83-0

Basic information

• Product Name: CINNOLIN-4-YLAMINE
• Synonyms: Cinnolin-4-ylamine;4-Cinnolinamine;4-AMinocinnoline;cinnolin-4-aMine
• CAS NO: 5152-83-0
• Molecular Formula: C8H7N3
• Molecular Weight: 145.16
• Mol File: 5152-83-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 209.5-210.5 °C
• Boiling Point: 351.8°C at 760 mmHg
• Flash Point: 193.7°C
• Appearance: /
• Density: 1.292g/cm³
• Vapor Pressure: 4E-05mmHg at 25°C
• Refractive Index: 1.723
• PKA: 6.98±0.10(Predicted)
• CAS DataBase Reference: CINNOLIN-4-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: CINNOLIN-4-YLAMINE(5152-83-0)
• EPA Substance Registry System: CINNOLIN-4-YLAMINE(5152-83-0)

Safety Data

• Hazardous Substances Data: 5152-83-0(Hazardous Substances Data)

Usage

General Description

Cinnolin-4-ylamine, also known as 4-aminoquinazoline, is an organic compound with the chemical formula C8H7N3. It is a derivative of cinnoline and contains an amino group at the 4-position of the quinazoline ring. Cinnolin-4-ylamine has a wide range of applications in the field of pharmaceuticals, as it is used as a building block in the synthesis of various biologically active molecules, including antiviral, antibacterial, and antitumor agents. Additionally, cinnolin-4-ylamine has been investigated for its potential use in the development of new materials and organic electronics due to its unique electronic and structural properties.

InChI:InChI=1/C8H7N3/c9-7-5-10-11-8-4-2-1-3-6(7)8/h1-5H,(H2,9,11)

Upstream product

• 143232-59-1 4-amino-3-cinnolinecarboxylic acid 
• 875-66-1 cinnolin-4-ol 
• 408508-53-2 4-phenoxy-cinnoline 
• 631-61-8 ammonium acetate 
• 5152-84-1 4-chlorocinnoline 

Downstream Products

• 99185-46-3 N-cinnolin-4-yl-acetamide 
• 875-66-1 cinnolin-4-ol 

Relevant articles and documents

Reactions of cinnoline, cinnoline N-oxides, and their chloro derivatives with alkylamines: The first case of nucleophilic substitution of hydrogen in the cinnoline series

In contrast to cinnoline and cinnoline N(1)-oxide, cinnoline N(2)-oxide reacts with primary and secondary amines on prolonged heating or in the presence of oxidants to give 3-alkylaminocinnolines.

On the tautomerism of cinnolin-4-ol, cinnoline-4-thiol, and cinnolin-4-amine

Detailed NMR spectroscopic investigations (1H, 13C, 15N) with cinnolin-4-ol (1) reveal this compound to exist exclusively in the cinnolin-4(1H)-one form in deuteriodimethyl sulfoxide solution. This finding is confirmed by comparison of the NMR spectroscopic data of 1 with those of the corresponding 'fixed' O-methyl and N-methyl derivatives, i.e. 4-methoxycinnoline (3) and 1-methylcinnolin-4(1H)-one (5). Similarly, cinnoline-4-thiol (4) is present in the thione form in deuteriodimethyl sulfoxide, whereas cinnolin-4-amine (7) exists in the amino form. In addition, in-depth analyses of the NMR spectra of some simple 4-substituted cinnolines are provided.

Metallation of diazines XIV. First O-directed metallation of cinnolines. Metallation of 3-, 4-chloro and 3-, 4-methoxycinnolines

The lithiation of 3-, 4-chloro and 3-, 4-methoxycinnolines was studied and good yields were obtained. When iodine was used as electrophile, 4,8-diiodo or 4,8-iodochloro compounds were prepared. A xanthone and diazepine were synthetized.