56-57-5 Usage
Description
4-Nitroquinoline N-Oxide is an organic compound with the chemical formula C9H6N2O3. It is a yellow crystalline solid that is soluble in organic solvents and slightly soluble in water. It has been identified as a potential carcinogen and mutagen, and its chemical properties and biological activities have been extensively studied.
Uses
Used in Cancer Research:
4-Nitroquinoline N-Oxide is used as a model compound in cancer research to study its carcinogenic effects. It has been found to induce DNA damage, mutations, and oxidative stress, leading to the development of cancer. Researchers use this compound to investigate the mechanisms of carcinogenesis and to develop potential therapeutic strategies for cancer prevention and treatment.
Used in Animal Models:
4-Nitroquinoline N-Oxide is used in the construction of animal models for oral mucosal malignancy related to Kras mutation. These animal models are essential for understanding the molecular and cellular mechanisms underlying the development and progression of oral cancer. They also help in evaluating the efficacy of potential therapeutic agents and interventions in a controlled and reproducible manner.
Air & Water Reactions
4-NITROQUINOLINE N-OXIDE is hygroscopic and light sensitive. Insoluble in water.
Reactivity Profile
4-NITROQUINOLINE N-OXIDE reacts with strong oxidizing agents.
Health Hazard
ACUTE/CHRONIC HAZARDS: 4-NITROQUINOLINE N-OXIDE may cause irritation. When heated to decomposition it may emit toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides.
Fire Hazard
Flash point data for 4-NITROQUINOLINE N-OXIDE are not available; however, 4-NITROQUINOLINE N-OXIDE is probably combustible.
Biochem/physiol Actions
Skin and lung tumor initiator under experimental conditions.
Safety Profile
Suspected carcinogen
with experimental carcinogenic, neoplas tigenic,
and tumorigenic data. Poison by
intraperitoneal and subcutaneous routes. An experimental teratogen. Other experimental
reproductive effects. Human mutation data
reported. When heated to decomposition it
emits toxic fumes of NOx.
Purification Methods
The N-oxide recrystallises from aqueous acetone as yellow needles or platelets. [Ochiai J Org Chem 18 534 1953, Seki et al. J Phys Chem 91 126 1987, Beilstein 20 III/IV 3396.]
Check Digit Verification of cas no
The CAS Registry Mumber 56-57-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 6 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 56-57:
(4*5)+(3*6)+(2*5)+(1*7)=55
55 % 10 = 5
So 56-57-5 is a valid CAS Registry Number.
InChI:InChI=1/C9H7N2O3/c12-10-6-5-9(11(13)14)7-3-1-2-4-8(7)10/h1-6,8H/q+1
56-57-5Relevant articles and documents
Nitration of quinoline 1-oxide: Mechanism of regioselectivity
Yokoyama, Akihiro,Ohwada, Tomohiko,Saito, Shinichi,Shudo, Koichi
, p. 279 - 283 (1997)
The acidity dependence of orientation in the nitration of quinoline 1- oxide was investigated by using the trifluoromethanesulfonic acid (TFSA)- trifluoroacetic acid (TFA) system and the antimony pentafluoride (SbF5)- TFSA system. These systems provide a wider range of acidity than that of aqueous sulfuric acid. Comparison of the behavior of quinoline 1-oxide and 1- methoxyquinolinium triflate in acidic and neutral media demonstrated that O- protonated quinoline 1-oxide is nitrated at the 5- and 8-positions, and the free (unprotonated) molecule is nitrated at the 4-position. This result is consistent with theoretical expectation. It was also discovered that nitration at the 5-position increasingly predominates over that at the 8- position as the acidity is increased.
Hypervalent Iodine(III)-Mediated Regioselective Cyanation of Quinoline N-Oxides with Trimethylsilyl Cyanide
Xu, Feng,Li, Yuqin,Huang, Xin,Fang, Xinjie,Li, Zhuofei,Jiang, Hongshuo,Qiao, Jingyi,Chu, Wenyi,Sun, Zhizhong
supporting information, p. 520 - 525 (2018/12/13)
A regioselective cyanation of quinoline N-oxides with trimethylsilyl cyanide was developed by using (Diacetoxyiodo) benzene (PIDA) as mediated hypervalent iodine(III) reagent under metal-free and base-free reaction conditions to obtain 2-cyanoquinolines. The efficient PIDA reagent could play the role of an activator of the substrates and an accelerator of N?O bond cleavage. The reaction system featured a wide range of substrate suitability and high yields. The procedure was enlarged gram-scale to synthesize the tuberculosis (TB) inhibitor. Finally, according to some experimental results, a plausible mechanism for the cyanation reaction is proposed. (Figure presented.).
Copper-catalyzed direct amination of quinoline N-oxides via C-H bond activation under mild conditions
Zhu, Chongwei,Yi, Meiling,Wei, Donghui,Chen, Xuan,Wu, Yangjie,Cui, Xiuling
supporting information, p. 1840 - 1843 (2014/05/06)
A highly efficient and concise one-pot strategy for the direct amination of quinoline N-oxides via copper-catalyzed dehydrogenative C-N coupling has been developed. The desired products were obtained in good to excellent yields for 22 examples starting from the parent aliphatic amines. This methodology provides a practical pathway to 2-aminoquinolines and features a simple system, high efficiency, environmental friendliness, low reaction temperature, and ligand, additives, base, and external oxidant free conditions.