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

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

Uses

Used in Pharmaceutical Industry:
Cinnolin-4-ylamine is used as a key building block for the synthesis of biologically active molecules due to its ability to contribute to the development of antiviral, antibacterial, and antitumor agents. Its presence in these molecules enhances their therapeutic effects, making it a valuable component in the creation of new pharmaceuticals.
Used in Material Development:
Cinnolin-4-ylamine is also used in the development of new materials, capitalizing on its unique electronic and structural properties. Its potential in this area is currently being explored, which could lead to advancements in various material sciences applications.
Used in Organic Electronics:
Furthermore, Cinnolin-4-ylamine has been investigated for its potential use in organic electronics. Its electronic properties make it a candidate for components in organic electronic devices, which could contribute to the development of more efficient and sustainable electronic technologies.

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

Upstream product

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

Downstream Products

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

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.

Synthesis, structures and biological activity of some 4-amino-3-cinnoline-carboxylic acid derivatives. Part 2

6,7,8-Substituted 4-amino-3-cinnolinecarboxylic acids 1 were condensed with amines to the corresponding 4-amino-3-cinnolinecarboxamides 7, 8. A variety of pharmacological tests showed a significant CNS activity of some new amides. Decarboxylation of 4-amino-3-cinnolinecarboxylic acids 1 yielded the corresponding 4-aminocinnolines 4 and alkaline hydrolysis of 1 gave 4-oxo-3-cinnolinecarboxylic acids 2. The acids 1 were converted into pyrimido[5,4-c]cinnolines 6 on two ways of synthesis.

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.