Methyl 8-hydroxyquinoline-2-carboxylate

Base Information

• Chemical Name: Methyl 8-hydroxyquinoline-2-carboxylate
• CAS No.: 21638-90-4
• Molecular Formula: C11H9 N O3
• Molecular Weight: 203.197
• Hs Code.: 2933499090
• ChEMBL ID: CHEMBL229585
• DSSTox Substance ID: DTXSID20491355
• Metabolomics Workbench ID: 127879
• Nikkaji Number: J1.529.289J
• Wikidata: Q82335816
• Mol file: 21638-90-4.mol

Synonyms:METHYL 8-HYDROXYQUINOLINE-2-CARBOXYLATE;21638-90-4;8-Hydroxy-quinoline-2-carboxylic acid methyl ester;2-Quinolinecarboxylicacid, 8-hydroxy-, methyl ester;8-hydroxy-2-quinolinecarboxylic acid methyl ester;SCHEMBL847651;CHEMBL229585;DTXSID20491355;DTYHRSIQPYNEJX-UHFFFAOYSA-N;8-hydroxyquinaldic acid methyl ester;AKOS016002766;SB68932;methyl 8-oxidanylquinoline-2-carboxylate;CS-0333603;FT-0726116;A815553;A878982;8-hydroxyl-quinoline-2-carboxylic acid methyl ester;31108-80-2

Chemical Property of Methyl 8-hydroxyquinoline-2-carboxylate

Chemical Property:

• Melting Point: 103-105 °C
• Boiling Point: 389.2±22.0 °C(Predicted)
• PKA: 9.26±0.10(Predicted)
• PSA: 59.42000
• Density: 1.327±0.06 g/cm3(Predicted)
• LogP: 1.72700
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 203.058243149
• Heavy Atom Count: 15
• Complexity: 244

Purity/Quality:

98.5% ^*data from raw suppliers

Methyl8-hydroxyquinoline-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=NC2=C(C=CC=C2O)C=C1

Technology Process of Methyl 8-hydroxyquinoline-2-carboxylate

There total 9 articles about Methyl 8-hydroxyquinoline-2-carboxylate 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: 96.0%

methanol (67-56-1) + 8-hydroxy-quinoline-2-carboxylic acid (1571-30-8) → methyl 8-hydroxyquinoline-2-carboxylate (21638-90-4)

Guidance literature:

With thionyl chloride; at 65 ℃; for 2h;

DOI:10.1021/np060626o

Reference yield:

2-formyl oxine (14510-06-6) → methyl 8-hydroxyquinoline-2-carboxylate (21638-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1: formic acid; dihydrogen peroxide / 8 h / 20 °C

2: thionyl chloride / 6 h / Cooling with ice; Reflux; Inert atmosphere

With formic acid; thionyl chloride; dihydrogen peroxide;

DOI:10.1016/j.saa.2019.117678

Reference yield:

2-methyl-8-quinolinol (826-81-3) → methyl 8-hydroxyquinoline-2-carboxylate (21638-90-4)

Guidance literature:

Multi-step reaction with 3 steps

1: selenium(IV) oxide

2: formic acid; dihydrogen peroxide / 8 h / 20 °C

3: thionyl chloride / 6 h / Cooling with ice; Reflux; Inert atmosphere

With selenium(IV) oxide; formic acid; thionyl chloride; dihydrogen peroxide;

DOI:10.1016/j.saa.2019.117678

upstream raw materials:

methanol

8-hydroxy-quinoline-2-carboxylic acid

xanthurenic acid

4-Chlor-8-hydroxychinaldinsaeure

Downstream raw materials:

8-Hydroxychinolin-2-carbonsaeurehydrazid

8-hydroxy-N’-(2-hydroxybenzylidene)quinoline-2-carbohydrazide

Refernces

• 1、 Huyen Vu, Thi,Serradji, Nawal,Seydou, Mahamadou,Brémond, éric,Ha-Duong, Nguyen-Thanh. "Electronic spectroscopic characterization of the formation of iron(III) metal complexes: The 8-HydroxyQuinoline as ligand case study". . . Retrieved 2020.
• 2、 Fu, Jiaxin,Li, Bai,Mei, Huihui,Chang, Yongxin,Xu, Kuoxi. "Fluorescent schiff base probes for sequential detection of Al3+ and F? and cell imaging applications". . . Retrieved 2019/11/11.
• 3、 -. "NEW COMPOUNDS". Page/Page column 100. . Retrieved 2013/03/26.