101327-87-1

Basic information

• Product Name: 8-Nitro-7-quinolinecarboxaldehyde
• Synonyms: 8-Nitro-7-quinolinecarboxaldehyde;7-Formyl-8-nitroquinoline;8-Nitroquinoline-7-carboxaldehyde;8-Nitro-7-quinolinecarbaldehyde
• CAS NO: 101327-87-1
• Molecular Formula: C₁₀H₆N₂O₃
• Molecular Weight: 202.168
• Mol File: 101327-87-1.mol

Chemical Properties

• Melting Point: 178.0 to 182.0 °C
• Boiling Point: 401.388°C at 760 mmHg
• Flash Point: 196.553°C
• Appearance: /
• Density: 1.441g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.721
• PKA: -0.66±0.31(Predicted)
• CAS DataBase Reference: 8-Nitro-7-quinolinecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Nitro-7-quinolinecarboxaldehyde(101327-87-1)
• EPA Substance Registry System: 8-Nitro-7-quinolinecarboxaldehyde(101327-87-1)

Safety Data

• Hazardous Substances Data: 101327-87-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
8-Nitro-7-quinolinecarboxaldehyde is used as a key intermediate in the synthesis of various organic compounds, leveraging its reactivity and structural features to form a wide range of derivatives.
Used as a Fluorescent Probe in Bioanalytical Applications:
8-Nitro-7-quinolinecarboxaldehyde is utilized as a fluorescent probe due to its inherent fluorescent properties, allowing for the detection and analysis of biological molecules and processes.
Used in Pharmaceutical Development:
8-Nitro-7-quinolinecarboxaldehyde is studied for its potential use in the development of pharmaceuticals, where its reactivity and fluorescent properties could be harnessed for the creation of new drugs or drug candidates.
Used in Materials Science for Fluorescent and Luminescent Properties:
8-Nitro-7-quinolinecarboxaldehyde is explored for its applications in materials science, particularly for the development of materials with fluorescent and luminescent properties, which can be used in various technological and scientific applications.
Used in Antimicrobial and Antiparasitic Research:
8-Nitro-7-quinolinecarboxaldehyde has been investigated for its potential antimicrobial and antiparasitic properties, with the aim of developing new treatments for infectious diseases.
Used in Different Industries:
8-Nitro-7-quinolinecarboxaldehyde is used across various industries, including pharmaceuticals, biotechnology, and materials science, for its diverse applications and potential to contribute to the development of new products and technologies.

InChI:InChI=1/C10H6N2O3/c13-6-8-4-3-7-2-1-5-11-9(7)10(8)12(14)15/h1-6H

Upstream product

• 122947-89-1 7-Dibromomethyl-8-nitro-quinoline 
• 101327-83-7 7-nitromethyl-8-nitroquinolin 
• 176853-39-7 7-<β-trans-(N,N-dimethylamino)ethenyl>-8-nitroquinoline 
• 7471-63-8 8-nitro-7-methylquinoline 
• 107-02-8 acrolein 
• 56-81-5 glycerol 
• 612-60-2 7-methylquinoline 
• 607-35-2 8-nitroquinoline 

Downstream Products

• 1394082-43-9 2-Phenyl-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxide 
• 1394085-43-8 (3-[1,3]dioxolan-2-yl-4-fluoro-phenyl)-(8-nitro-quinolin-7-yl)-methanol 
• 1394085-12-1 (3-fluoro-phenyl)-(8-nitro-quinolin-7-yl)-methanone 
• 1394084-82-2 (8-nitro-quinolin-7-ylmethyl)-phenyl-amine 
• 1394082-45-1 2-Methyl-1-phenyl-1,4-dihydro-2H-3-thia-2,4,5-triaza-phenanthrene 3,3-dioxide 
• 1394084-88-8 (8-amino-quinolin-7-yl)-phenyl-methanol 
• 1394084-83-3 7-phenylaminomethyl-quinolin-8-ylamine 
• 1394084-96-8 (3-fluoro-phenyl)-(8-nitro-quinolin-7-yl)-methanol 
• 1394084-87-7 (8-nitro-quinolin-7-yl)-phenyl-methanol 
• 109559-47-9 2-phenyl-1,10-phananthroline 
• 158753-17-4 8-amino-7-quinolinecarbaldehyde 

Relevant articles and documents

Design and synthesis of chiral 1,10-phenanthroline ligand, and application in palladium catalyzed asymmetric 1,4-addition reactions

Pd-catalyzed asymmetric 1,4-addition of phenylboronic acid to α,β-unsaturated carbonyl compounds was developed using chiral 1,10-phenanthroline derivative as ligand. Good yields (up to 97%), and high enantioselectivities (up to 97% ee) were achieved.

Merging Annulation with Ring Deconstruction: Synthesis of (E)-3-(2-Acyl-1 H-benzo[ d]imidazol-4-yl)acrylaldehyde Derivatives via I2/FeCl3-Promoted Dual C(sp3)-H Amination/C-N Bond Cleavage

An unprecedented I2/FeCl3-promoted cascade reaction of aryl methyl ketones with 8-aminoquinolines for the convenient synthesis of (E)-3-(2-acyl-1H-benzo[d]imidazol-4-yl)acrylaldehydes was developed by merging annulation with ring deconstruction. This novel strategy unlocked the new reactivity of 8-aminoquinolines and provided an attractive platform for the ring opening of unactivated N-heteroaromatic compounds. Preliminary mechanistic investigation suggested that dual C(sp3)-H amination/C-N bond cleavage were key reaction steps. Furthermore, late-stage modification of the obtained products successfully delivered pyrazole and isoxazole derivatives, increasing the practicability and application potential of this methodology in organic synthesis.

Novel Sulfonaminoquinoline Hepcidin Antagonists

The present invention relates to novel hepcidin antagonists, pharmaceutical compositions comprising them and the use thereof as medicaments for the use in the treatment of iron metabolism disorders, such as, in particular, iron deficiency diseases and anemias, in particular anemias in connection with chronic inflammatory diseases.

Introduction of benzo[h]quinoline and 1,10-phenanthroline subunits by friedl?nder methodology

An improved preparation of 8-amino-7-quinolinecarbaldehyde has been developed. The methyl group of 7-methyl-8-nitroquinoline may be oxidized to an aldehyde by treatment first with dimethylformamide dimethyl acetal followed by sodium periodate. Reduction with iron provides the amino aldehyde. An analogous sequence affords 1-amino-2-naphthalenecarbaldehyde. Friedl?nder condensation of the quinoline derivative with a series of acetylaromatics provides the corresponding 2-aryl-1,10-phenanthrolines. Condensation of either amino aldehyde with 1,3-diacetylbenzene or 2,6-diacetylpyridine provides the expected Friedl?nder product. Similar chemistry is described for reactions of the amino aldehydes with 1,4-diacetylbenzene, 4,4′-diacetylbiphenyl, 1,5-diacetylanthracene, 1,2,3,4,5,6,7,8-octahydroacridine-1,8-dione, and tetracyclo-[6.3.0.0.4,1105,9]undecane-2,7-dione (TCU-2,7-dione).

Dihalomethylation of Nitroarenes via Vicarious Nucleophilic Substitution of Hydrogen with Trihalomethyl Carbanions

Trichloro- and tribromomethyl carbanions generated by deprotonation of haloforms with potassium tert-butoxide in a THF-DMF mixture at ca. -70 deg C react with a variety of carbocyclic and heterocyclic nitroarenes according to the vicarious nucleophilic substitution scheme.The reaction provides an efficient and convenient way for the direct introduction of dihalomethyl substituents ortho and para to the nitro group, which in turn can be hydrolyzed to produce nitroaryl aldehydes.

DIRECT NITROMETHYLATION OF NITRONAPHTHALENE AND ITS HETEROANALOGUES A NEW METHOD FOR FUNCTIONALIZATION OF NITROARENES

Some nitroarenes react with nitromethane anion to form nitromethyl derivatives which are easily converted into corresponding nitroaromatic aldehydes.