4-Hydroxy-6-methylquinoline

Base Information

• Chemical Name: 4-Hydroxy-6-methylquinoline
• CAS No.: 23432-40-8
• Molecular Formula: C10H9 N O
• Molecular Weight: 159.188
• Hs Code.: 2933499090
• European Community (EC) Number: 803-466-0
• NSC Number: 82351
• DSSTox Substance ID: DTXSID30292411
• Nikkaji Number: J1.612.031F,J2.447.352J
• Wikidata: Q82030706
• ChEMBL ID: CHEMBL1542315
• Mol file: 23432-40-8.mol

Synonyms:4-Hydroxy-6-methylquinoline;6-Methylquinolin-4-ol;23432-40-8;6-methylquinolin-4(1H)-one;97545-52-3;4-Quinolinol, 6-methyl-;6-methyl-1H-quinolin-4-one;6-methyl-4-quinolinol;6-methyl-quinolin-4-ol;MLS000517807;KUC100212;MFCD00272343;NSC82351;6-Methylquinoline-4(1H)-one;SCHEMBL5539379;CHEMBL1542315;6-Methyl-(1H)-quinolin-4-one;DTXSID30292411;HMS2212P15;HMS3338P12;KUC100212N;AMY13687;YAA43240;6-METHYL-4(1H)-QUINOLINONE;NSC 82351;NSC-82351;STL352805;ETHYLTRI-N-PROPYLAMMONIUMIODIDE;AKOS001776845;AKOS002337273;AB05625;CS-W004523;SB67749;4-Hydroxy-6-methylquinoline, AldrichCPR;DS-13102;SMR000129052;FT-0618668;FT-0647361;C74209;4-Quinolinol,6-methyl;A878244;J-650132;F3222-3754

Chemical Property of 4-Hydroxy-6-methylquinoline

Chemical Property:

• Vapor Pressure: 0.00208mmHg at 25°C
• Boiling Point: 290.3°Cat760mmHg
• Flash Point: 131.4°C
• PSA: 33.12000
• Density: 1.15g/cm³
• LogP: 2.24880
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 159.068413911
• Heavy Atom Count: 12
• Complexity: 222

Purity/Quality:

98%min ^*data from raw suppliers

6-Methylquinolin-4-ol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)NC=CC2=O

Technology Process of 4-Hydroxy-6-methylquinoline

There total 27 articles about 4-Hydroxy-6-methylquinoline 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: 87.0%

6-methyl-2,3-dihydroquinolin-4(1H)-one (36054-00-9) → 6-methyl-4(1H)-quinolinone (23432-40-8,97545-52-3)

Guidance literature:

With palladium 10% on activated carbon; sodium hydroxide; In water; isopropyl alcohol; for 16h; Inert atmosphere; Reflux;

DOI:10.1071/CH10465

Reference yield: 83.0%

1-(2-isocyano-5-methylphenyl)ethan-1-one → 4-hydroxy-6-methylquinoline (23432-40-8)

Guidance literature:

With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 6h; chemoselective reaction;

DOI:10.1021/acs.joc.9b02903

Reference yield: 76.0%

3-(dimethylamino)-1-(3-methylphenyl)-2-propen-1-one → 6-methyl-4(1H)-quinolinone (23432-40-8,97545-52-3)

Guidance literature:

3-(dimethylamino)-1-(3-methylphenyl)-2-propen-1-one; With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; potassium acetate; 3-phenyl-5H-1,4,2-dioxazol-5-one; In 1,4-dioxane; at 100 ℃; for 12h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; at 30 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b00583

upstream raw materials:

4-hydroxy-6-methyl-quinoline-3-carboxylic acid

2,2-Dimethyl-5-(p-tolylamino-methylene)-[1,3]dioxane-4,6-dione

ethyl 4-hydroxy-6-methylquinoline-3-carboxylate

p-toluidine

Downstream raw materials:

4-chloro-6-methylquinoline

6-methylquinoline

1,6-dimethylquinolin-4(1H)-one

C₁₈H₁₅NO₃

Refernces

• 1、 Shaldam, Moataz,Nocentini, Alessio,Elsayed, Zainab M.,Ibrahim, Tamer M.,Salem, Rofaida,El-Domany, Ramadan A.,Capasso, Clemente,Supuran, Claudiu T.,Eldehna, Wagdy M.. "Development of novel quinoline-based sulfonamides as selective cancer-associated carbonic anhydrase isoform ix inhibitors". . . Retrieved 2021/10/19.
• 2、 Wang, Fen,Jin, Liang,Kong, Lingheng,Li, Xingwei. "Cobalt(III)- and Rhodium(III)-Catalyzed C-H Amidation and Synthesis of 4-Quinolones: C-H Activation Assisted by Weakly Coordinating and Functionalizable Enaminone". supporting information. p. 1812 - 1815. Retrieved 2017/04/11.