2-(4-METHOXYPHENYL)QUINOLINE

Base Information

• Chemical Name: 2-(4-METHOXYPHENYL)QUINOLINE
• CAS No.: 16032-40-9
• Molecular Formula: C16H13NO
• Molecular Weight: 235.285
• Mol file: 16032-40-9.mol

Synonyms:2-(4-methoxyphenyl)-3H-quinazolin-4-one;2-(4'-methoxyphenyl)quinoline;2-(4-Methoxyphenyl)-chinolin;2-[4-(methyloxy)phenyl]quinazolin-4(3H)-one;2-(4-methoxyphenyl)quinazolin-4-ol;2-(4-methoxyphenyl)quinazolin-4(3H)-one;2-(p-methoxyphenyl)quinazolin-4(3H)-one;2-(p-methoxyphenyl)-4(3H)quinazolinone;2-(p-methoxyphenyl)quinoline;

Chemical Property of 2-(4-METHOXYPHENYL)QUINOLINE

Chemical Property:

• Melting Point: 122-124℃
• Boiling Point: 398℃
• PKA: 4.76±0.30(Predicted)
• Flash Point: 144℃
• PSA: 22.12000
• Density: 1.141
• LogP: 3.91040

Purity/Quality:

98%min ^*data from raw suppliers

2-(4-METHOXYPHENYL)QUINOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(4-METHOXYPHENYL)QUINOLINE

There total 122 articles about 2-(4-METHOXYPHENYL)QUINOLINE 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: 99.0%

(E)-3-(2-aminophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one → 2-(4-methoxyphenyl)quinoline (16032-40-9)

Guidance literature:

With benzylamine; In water; at 80 ℃; for 1h;

DOI:10.1021/acs.joc.8b01675

Reference yield: 97.0%

2-Aminobenzyl alcohol (5344-90-1) + 1-(4-methoxyphenyl)ethanone (100-06-1) → 2-(4-methoxyphenyl)quinoline (16032-40-9)

Guidance literature:

With iron(III) oxide; potassium tert-butylate; In toluene; for 15h; Inert atmosphere; Sealed tube;

DOI:10.1039/c9cc04120f

Reference yield: 97.0%

quinoline (91-22-5) + 4-methoxyphenylboronic acid (5720-07-0) → 2-(4-methoxyphenyl)quinoline (16032-40-9)

Guidance literature:

4-methoxyphenylboronic acid; With diethylzinc; In 1,4-dioxane; at 60 ℃; for 12h;

quinoline; With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; tricyclohexylphosphine; In 1,4-dioxane; toluene; at 130 ℃; for 20h;

DOI:10.1021/ja9053509

upstream raw materials:

4-methoxy-benzaldehyde

aniline

1-bromo-4-methoxy-benzene

2-[3-hydroxy-3-(p-methoxyphenyl)prop-1-ynyl]trifluoroacetanilide

Downstream raw materials:

2-(4-hydroxyphenyl)-1-methylquinolin-4(1H)-one

2-(4-methoxyphenyl)quinoline hydrobromide

4-chloro-2-(4-methoxyphenyl)-1,2-dihydroquinoline-1,3-dicarbaldehyde

8-iodo-2-(3-iodo-4-methoxyphenyl)quinoline

Refernces

• 1、 Cho, Chan Sik,Lee, Na Young,Kim, Tae-Jeong,Shim, Sang Chul. "Consecutive isomerization and cyclization of 3-(2-Aminophenyl)-1-arylprop- 2-yn-1-ols leading to 2-arylquinolines in the presence of potassium hydroxide". . p. 409 - 411. Retrieved 2004.
• 2、 Cho, Chan Sik,Kim, Bok Tae,Kim, Tae-Jeong,Shim, Sang Chul. "Ruthenium-catalysed oxidative cyclisation of 2-aminobenzyl alcohol with ketones: modified Friedlaender quinoline synthesis". . p. 2576 - 2577. Retrieved 2001.
• 3、 Sudhapriya, Narayanasamy,Nandakumar, Avanashiappan,Perumal, Paramasivan Thirumalai. "Facile synthesis of 2-substituted quinolines and 3-alkynyl-2-aryl-2H-Indazole via SnCl2-mediated reductive cyclization". . p. 58476 - 58480. Retrieved 2014.
• 4、 Cho, Chan Sik,Kim, Bok Tae,Choi, Heung-Jin,Kim, Tae-Jeong,Shim, Sang Chul. "Ruthenium-catalyzed oxidative coupling and cyclization between 2-aminobenzyl alcohol and secondary alcohols leading to quinolines". . p. 7997 - 8002. Retrieved 2003.
• 5、 Cho, Chan Sik. "Palladium-catalyzed Sonogashira coupling reaction followed by isomerization and cyclization". . p. 4094 - 4097. Retrieved 2005.
• 6、 Sangu, Kenichiro,Fuchibe, Kohei,Akiyama, Takahiko. "A Novel Approach to 2-Arylated Quinolines: Electrocyclization of Alkynyl Imines via Vinylidene Complexes". . p. 353 - 355. Retrieved 2004.
• 7、 Ghora, Santanu,Sreenivasulu, Chinnabattigalla,Satyanarayana, Gedu. "A Domino Heck Coupling-Cyclization-Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines". . p. 393 - 402. Retrieved 2021/10/21.
• 8、 Blakemore, David C.,Cervantes-Reyes, Alejandro,Chinigo, Gary M.,Smith, Aaron C.,Szostak, Michal. "Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls". supporting information. p. 1678 - 1683. Retrieved 2022/03/14.