17576-53-3

Basic information

• Product Name: 3-Nitroquinoline
• Synonyms: Quinoline, 3-nitro-
• CAS NO: 17576-53-3
• Molecular Formula: C₉H₆N₂O₂
• Molecular Weight: 174.1561
• Mol File: 17576-53-3.mol

Chemical Properties

• Melting Point: 128 °C
• Boiling Point: 317.4 °C at 760 mmHg
• Flash Point: 145.8 °C
• Appearance: /
• Density: 1.354 g/cm³
• Vapor Pressure: 0.000718mmHg at 25°C
• Refractive Index: 1.682
• Storage Temp.: 2-8°C
• PKA: 1.15±0.11(Predicted)
• CAS DataBase Reference: 3-Nitroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Nitroquinoline(17576-53-3)
• EPA Substance Registry System: 3-Nitroquinoline(17576-53-3)

Safety Data

• Hazardous Substances Data: 17576-53-3(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
3-Nitroquinoline is used as a mutagen for [studying cancer and genetic mutation processes] because of its ability to stimulate mutations and genetic alterations that might lead to cancer. Its interaction with DNA and the substitution of nucleic acids during cell replication make it a valuable tool in understanding the mechanisms behind these processes.
Used in Cancer Research:
3-Nitroquinoline is used as a research compound for [investigating the development and progression of cancer] due to its mutagenic properties. 3-Nitroquinoline's ability to induce genetic mutations provides insights into the factors that contribute to the onset and growth of cancerous cells.
Used in Genetic Studies:
3-Nitroquinoline is used as a mutagen for [exploring the effects of genetic mutations on cellular functions and organismal development]. Its role in causing genetic alterations can help researchers understand the consequences of mutations on an organism's genetic makeup and overall health.

InChI:InChI=1/C9H6N2O2/c12-11(13)8-5-7-3-1-2-4-9(7)10-6-8/h1-6H

Upstream product

• 91-22-5 quinoline 
• 7433-86-5 3-nitroquinoline N-oxide 
• 5466-50-2 3-Nitro-cinchoninsaeure 
• 40824-87-1 3-anilino-2-nitro-acrylaldehyde 
• 142-04-1 aniline hydrochloride 
• 64-19-7 acetic acid 
• 5653-21-4 metazonic acid 
• 529-23-7 o-aminobenzaldehyde 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 3156-51-2 3-[(E)-2-nitroeth-1-enyl]-1H-indole 
• 3638-64-0 1-nitroethylene 

Downstream Products

• 580-17-6 3-aminoquinoline 
• 7433-86-5 3-nitroquinoline N-oxide 
• 42606-33-7 3-nitro-4-aminoquinoline 
• 99009-86-6 4-(methylamino)-3-nitroquinoline 
• 145297-30-9 3-Nitro-4-phenylquinoline 
• 79965-62-1 3-nitro-4-methylquinoline 

Relevant articles and documents

Regiospecific nitration of quinoline and isoquinoline through the Reissert compounds

Regiospecific nitration of quinoline and isoquinoline was achieved via the Reissert compounds by treatment with acetyl nitrate. Nitration of 1-benzoyl-2-cyanoquinoline (3) afforded the 3-nitro derivative, which was converted to 3-nitroquinoline by hydrolysis with concentrated HCl. Meanwhile, 2-benzoyl-1-cyano-1,2-dihydroisoquinoline (4) was converted ultimately into 4-nitroisequinoline-1-carboxylic acid (10) via 4-nitro-1-cyanoisoquinoline by the same procedure. A novel method for introducing a nitro group at the β-position of a heterocyclic moiety has thus been developed. Crystal structure determinations and molecular orbital calculations of the Reissert compounds, are consistent with the regiospecific nitration.

Metal-free regioselective C-3 nitration of quinoline N-oxides with tert-butyl nitrite

A direct and eco-friendly nitration methodology to synthesize 3-nitroquinoline N-oxides from quinoline N-oxides using tert-butyl nitrite as both the nitro source and oxidant has been developed. Although this reaction undergoes a free radical process, it exhibits high regioselectivity and can be smoothly scaled up to gram scale. This journal is

Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution

Electrophilic nitropyridines react with sulfonyl-stabilized carbanions to give products of C-H alkylation via vicarious nucleophilic substitution. The process consists of formation of the Meisenheimer-type adduct followed by base-induced β-elimination of the sulfinic acid (e.g., PhSO2H). Mechanistic studies reveal that in the latter step alkyl substituent and adjacent nitro group tend to planarize for effective stabilization of benzyl anion, and thus, adduct of hindered isopropyl carbanion remains stable toward elimination for steric reasons.

Bismuth nitrate as a source of nitro radical in ipso-nitration of carboxylic acids

Aromatic nitro compounds are extensively used in synthetic chemistry. We disclose a new approach to obtain nitroarenes regioselectively starting from carboxylic acids under acid-free reaction conditions.

Method for nitrating aromatic compound by using nitrate under the action of auxiliary agent

The invention discloses a method for nitrating an aromatic compound by using a nitrate under the action of an auxiliary agent, and provides an aromatic nitro compound preparation method, which comprises: in the presence of an external action and an auxiliary agent, carrying out a nitrating reaction on an aromatic compound and a metal nitrate or a hydrate thereof to obtain the aromatic nitro compound, wherein the external action can cause the physical and/or chemical property change of a substance, the auxiliary agent is a substance having water absorbing ability, the external action can be mechanical force or heating, and the mechanical force can be any one selected from compression, shearing, impacting, friction, stretching, bending and vibration. According to the present invention, the method does not require any solvents so as to avoid the generation of the waste liquid; the acidic substance is not used, such that the treatment is simple after the reaction is completed, and the equipment is not damaged; the added auxiliary agent can be theoretically recycled; and the method has extremely high conversion rate and extremely high selectivity, and can be used for the nitration of conventional aromatic compounds.

Mechanical force under the action of the nitration of aromatic compounds of nitrate method (by machine translation)

The invention discloses a mechanical force under the action of the nitration of aromatic compounds of nitrate method. The invention provides a method for preparing aromatic nitro compounds, comprising the following steps: under the action of mechanical force, aromatic compound with a metal nitrate or its hydrate by the nitration reaction, to obtain the aromatic nitro compound; the mechanical fastener is machinery offers can cause material physical and/or chemical nature of the change of the external force. The mechanical force can be compression, shear, impact, friction, tensile, bending and vibration of any kind. The invention has the following advantages: without the use of any solvent, thereby avoiding the waste liquid produced; and without the use of the acidic substance, the reaction is complete after treatment is simple, without any damage to the apparatus; a very high conversion and selectivity, can be applied to the nitration of conventional aromatic compound. (by machine translation)

Ipso-nitration of arylboronic acids with bismuth nitrate and perdisulfate

An efficient and one pot synthetic method of ipso-nitration of arylboronic acids has been developed. The high efficiency, general applicability, and broader substrate scope including heterocycles and functional groups make this method advantageous. Due to its simplicity, we expect to find application of this method in synthesis.

Copper catalyzed ipso-nitration of iodoarenes, bromoarenes and heterocyclic haloarenes under ligand-free conditions

A catalytic protocol for the conversion of haloarenes into the corresponding nitroarenes is presented using copper salts under ligand-free conditions. The method was effectively utilized for the ipso-nitration of a broad variety of haloarenes that includes iodoarenes, bromoarenes, and heterocyclic haloarenes.

Selective oxidation of aromatic amines to nitro derivatives using potassium iodide-tert-butyl hydroperoxide catalytic system

The direct oxidation of aromatic primary amines to the corresponding nitro compounds selectively in 47-98% yields has been achieved by using potassium iodide as catalyst and tert-butyl hydroperoxide as the external oxidant. The present catalytic system works well for both electron-rich and electron-poor substrates.

An Investigation of the Reaction of 2-Aminobenzaldehyde Derivatives with Conjugated Nitro-olefins: An Easy and Efficient Synthesis of 3-Nitro-1,2-dihydroquinolines and 3-Nitroquinolines

2-Aryl-3-nitro-1,2-dihydroquinolines 3 were prepared from the reaction of β-nitrostyrenes 2 and 2-aminobenzaldehyde 1 in the presence of DABCO. Not only β-nitrostyrenes but other alkyl nitro olefins also can be used in this reaction as well. When DDQ or silica gel was added to a solution of 3-nitro-1,2-dihydroquinolines 3, 3-nitro-2-substituted-quinolines 4 were obtained. When 2-aminobenzaldehyde derivatives 7 and 12 were reacted with β-nitrostyrenes 2, unique rearrangement products were produced.