8-Hydroxyquinoline 1-oxide

Base Information

• Chemical Name: 8-Hydroxyquinoline 1-oxide
• CAS No.: 1127-45-3
• Molecular Formula: C9H7NO2
• Molecular Weight: 161.16
• Hs Code.: 29334900
• European Community (EC) Number: 214-430-3
• NSC Number: 21656
• UNII: TMI4LD989P
• DSSTox Substance ID: DTXSID70150142
• Nikkaji Number: J29.081E
• Wikidata: Q27290026
• ChEMBL ID: CHEMBL1650601
• Mol file: 1127-45-3.mol

Synonyms:1127-45-3;8-Hydroxyquinoline-N-oxide;8-Hydroxyquinoline 1-oxide;8-Hydroxyquinoline N-oxide;8-Quinolinol, 1-oxide;1-oxidoquinolin-1-ium-8-ol;8-HYDROXYQUINOLIN-N-OXIDE;o-Hydroxyquinoline N-oxide;8-Quinolinol N-oxide;Quinolin-8-ol 1-oxide;8-QUINOLINOL, N-OXIDE;MFCD00006739;MLS002638801;CCRIS 4451;EINECS 214-430-3;NSC 21656;NSC-21656;BRN 0128737;8-hydroxyquinolin-1-ium-1-olate;NSC21656;ACIDVIOLET6BN;quinolin-8-ol-N-oxide;8-Hydroxychinolin-N-oxid;8-Hydroxyquinoline1-oxide;8-Hydroxyquinolin N-oxide;UNII-TMI4LD989P;OXYQUINOLINE N-OXIDE;TMI4LD989P;SCHEMBL100824;8-Quinolinol N-oxide, 98%;CHEMBL1650601;DTXSID70150142;CHEBI:192375;HMS3082E11;1-oxo-1lambda(5)-quinolin-8-ol;AKOS015897108;HYDROXYQUINOLINE 1-OXIDE, 8-;AC-7833;AS-13601;SMR001548266;SY009330;LS-142579;FT-0633376;H1272;5-21-03-00276 (Beilstein Handbook Reference);W-108639;Q27290026

Chemical Property of 8-Hydroxyquinoline 1-oxide

Chemical Property:

• Appearance/Colour: Yellow crystalline solid
• Vapor Pressure: 2.12E-06mmHg at 25°C
• Melting Point: 71-73 °C(lit.)
• Refractive Index: 1.627
• Boiling Point: 382.6 °C at 760 mmHg
• PKA: 6.03±0.30(Predicted)
• Flash Point: 185.2 °C
• PSA: 45.69000
• Density: 1.28 g/cm³
• LogP: 1.97390
• Storage Temp.: Refrigerator
• Solubility.: Soluble in Acetone, Chloroform, Dichloromethane, Ethyl Acetate and Methanol
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 161.047678466
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

8-Quinolinol N-oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N, Xi
• Hazard Codes: N,Xi
• Statements: 50/53-36/37/38
• Safety Statements: 60-61-24/25-22-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)O)[N+](=CC=C2)[O-]
• Description: A quinoline derivative that displays mutagenic activity. It suppresses luminescence of an indicator bacterium that is named Photobacterium phosphoreum. This chemical forms two kinds of complexes with palladium (II) and Gold (III). One kind is an ion-associated compound containing hydrogen bond and hte other is the six membered metal chelates containing metal-oxygen bonds.
• Uses: A quinoline derivative; shows mutagenic activity.

Technology Process of 8-Hydroxyquinoline 1-oxide

There total 7 articles about 8-Hydroxyquinoline 1-oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

8-quinolinol (148-24-3,24804-14-6) → 8-Hydroxyquinoline-N-oxide (1127-45-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1007/PL00005339

Reference yield:

8-quinolinol (148-24-3,24804-14-6) + 3-chloroperbenzoic acid (MCPBA) → 8-Hydroxyquinoline-N-oxide (1127-45-3) + 8-[(2,3,4,5-Tetrahydro-2-methyl-4-methylene-5-oxo-2-furanyl)methoxy]-2(1H)-quinolinone

Guidance literature:

In dichloromethane;

Reference yield:

8-quinolinol (148-24-3,24804-14-6) + m-chloroperoxybenzoic acid (64741-01-1) → 8-Hydroxyquinoline-N-oxide (1127-45-3)

Guidance literature:

In chloroform;

upstream raw materials:

peracetic acid

8-quinolinol

Perbenzoic acid

monoperoxyphthalic acid

Downstream raw materials:

1-oxy-5-phenylazo-quinolin-8-ol

2-hydroxyquinolin-8-yl acetate

5-nitro-8-hydroxyquinoline-N-oxide

5,7-dinitro-8-hydroxyquinoline-N-oxide

Refernces

• 1、 Baran, Peter,Harmo?ová, Michaela,Ilic, Aleksandar,Lük?ová, Andrea,Litecká, Miroslava,Poto?ňák, Ivan,Vilková, Mária,Volarevic, Vladislav. "Low-dimensional compounds containing bioactive ligands. Part XVI: Halogenated derivatives of 8-quinolinol N-oxides and their copper(II) complexes". . . Retrieved 2021.
• 2、 Zhao, Yangyang,Qian, Guoliang,Ye, Yonghao,Wright, Stephen,Chen, Haotong,Shen, Yuemao,Liu, Fengquan,Du, Liangcheng. "Heterocyclic Aromatic N-Oxidation in the Biosynthesis of Phenazine Antibiotics from Lysobacter antibioticus". . p. 2495 - 2498. Retrieved 2016.
• 3、 Effendi, Nurmaya,Ogawa, Kazuma,Mishiro, Kenji,Takarada, Takeshi,Yamada, Daisuke,Kitamura, Yoji,Shiba, Kazuhiro,Maeda, Takehiko,Odani, Akira. "Synthesis and evaluation of radioiodinated 1-{2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}piperidin-4-amine derivatives for platelet-derived growth factor receptor β (PDGFRβ) imaging". . p. 5576 - 5585. Retrieved 2017.
• 4、 Yang, Yin,Huang, Feng,Huber, Thomas,Su, Xun-Cheng. "Site-specific tagging proteins with a rigid, small and stable transition metal chelator, 8-hydroxyquinoline, for paramagnetic NMR analysis". . p. 103 - 113. Retrieved 2016.
• 5、 Storz, Thomas,Marti, Roger,Meier, Roland,Nury, Patrice,Roeder, Michael,Zhang, Kesheng. "First safe and practical synthesis of 2-amino-8-hydroxyquinoline". . p. 663 - 665. Retrieved 2004.
• 6、 Chen, Guohong,Wang, Xin,Jin, Xiaoqian,Liu, Lingyan,Chang, Weixing,Li, Jing. "Allyltin tribromide: A versatile reagent involved in the ring-opening of epoxides". . p. 1294 - 1301. Retrieved 2010.
• 7、 Ferlin, Francesco,Zangarelli, Agnese,Lilli, Simone,Santoro, Stefano,Vaccaro, Luigi. "Waste-minimized synthesis of C2 functionalized quinolines exploiting iron-catalysed C-H activation". supporting information. p. 490 - 495. Retrieved 2021/01/28.
• 8、 Palav, Amey,Misal, Balu,Ernolla, Anilkumar,Parab, Vinod,Waske, Prashant,Khandekar, Dileep,Chaudhary, Vinay,Chaturbhuj, Ganesh. "The M?CPbA?NH3(G) system: A safe and scalable alternative for the manufacture of (substituted) pyridine and quinoline N?oxides?". supporting information. p. 244 - 251. Retrieved 2019/03/17.