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:

98% ^*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-]
• General Description: 8-Hydroxyquinoline-N-oxide is an efficient ligand used in copper-catalyzed hydroxylation reactions of aryl halides (iodides, bromides, and chlorides) to synthesize phenols under mild conditions. It works in conjunction with copper iodide (CuI) as the catalyst, cesium hydroxide (CsOH) as the base, and a DMSO/H2O solvent system. This ligand contributes to the reaction's high functional group tolerance, selectivity, and cost-effectiveness, enabling the conversion of aryl halides to phenols and facilitating one-pot synthesis of alkyl aryl ethers.

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

Highly efficient synthesis of phenols by copper-catalyzed hydroxylation of aryl iodides, bromides, and chlorides

10.1021/ol2016737

The research presents a highly efficient method for synthesizing phenols through the copper-catalyzed hydroxylation of aryl iodides, bromides, and chlorides under mild reaction conditions. The key chemicals involved include 8-hydroxyquinolin-N-oxide, which serves as an efficient ligand, and copper iodide (CuI) as the catalyst. The reaction system also utilizes cesium hydroxide (CsOH) as the base and a DMSO/H2O solvent mixture. This method is notable for its functional group tolerance and selectivity, making it a practical and cost-effective approach for converting aryl halides to phenols. Additionally, the protocol allows for the one-pot synthesis of alkyl aryl ethers from aryl halides and alkyl halides, further expanding its utility in organic synthesis.