6-Methoxy-2-methylquinoline

Base Information

• Chemical Name: 6-Methoxy-2-methylquinoline
• CAS No.: 1078-28-0
• Molecular Formula: C11H11NO
• Molecular Weight: 173.214
• Hs Code.: 29334900
• European Community (EC) Number: 214-080-1
• NSC Number: 15557
• UNII: YC360F525A
• DSSTox Substance ID: DTXSID70148246
• Nikkaji Number: J143.875A
• Wikidata: Q72485962
• Mol file: 1078-28-0.mol

Synonyms:6-Methoxyquinaldine;6-Methoxy-2-methylquinoline;1078-28-0;2-Methyl-6-methoxyquinoline;Quinoline, 6-methoxy-2-methyl-;Quinaldine, 6-methoxy-;YC360F525A;EINECS 214-080-1;NSC 15557;NSC-15557;NSC15557;6-Methoxyquinaldine, 97%;6-methoxy-2-methyl-quinoline;SCHEMBL806266;UNII-YC360F525A;DTXSID70148246;AMY10250;BAA07828;MFCD00006761;STK009858;AKOS000521025;CS-W005964;FS-1042;SB67452;FT-0621201;M1414;EN300-171394;F17645;A801764;SR-01000395952;SR-01000395952-1

Chemical Property of 6-Methoxy-2-methylquinoline

Chemical Property:

• Appearance/Colour: Beige to grey fluffy crystalline powder
• Vapor Pressure: 0.00467mmHg at 25°C
• Melting Point: 62-64 °C(lit.)
• Refractive Index: 1.599
• Boiling Point: 286.003 °C at 760 mmHg
• PKA: 5.87±0.43(Predicted)
• Flash Point: 104.905 °C
• PSA: 22.12000
• Density: 1.103 g/cm³
• LogP: 2.55180
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 173.084063974
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

99% ^*data from raw suppliers

6-Methoxy-2-methylquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC2=C(C=C1)C=C(C=C2)OC
• Uses: 6-Methoxyquinaldine was used in the preparation and characterization of three RNA-specific fluorescent probes (E36, E144and F22) and their applications in live cell imaging.

Technology Process of 6-Methoxy-2-methylquinoline

There total 67 articles about 6-Methoxy-2-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: 97.0%

6-methoxy-2-methyl-1,2,3,4-tetrahydroquinoline (42835-96-1,199186-62-4) → 6-methoxyquinaldine (1078-28-0)

Guidance literature:

With C₂₁H₂₁ClIrNO₂; In tetrahydrofuran; 2,2,2-trifluoroethanol; for 20h; Inert atmosphere;

DOI:10.1002/anie.201300292

Reference yield: 94.0%

4-methoxy-aniline (104-94-9) + crotonaldehyde (123-73-9,4170-30-3) → 6-methoxyquinaldine (1078-28-0)

Guidance literature:

With phosphomolybdic acid; sodium dodecyl-sulfate; In water; toluene; at 80 ℃; for 0.833333h;

DOI:10.1080/00397910903245141

Reference yield: 94.0%

trans-Crotonaldehyde (123-73-9,4170-30-3) + 4-methoxy-aniline (104-94-9) → 6-methoxyquinaldine (1078-28-0)

Guidance literature:

With phospho-tungstic acid; phosphotungstic acid; silica gel; for 0.166667h; microwave irradiation;

DOI:10.1016/j.tetlet.2006.01.034

upstream raw materials:

4-chloro-6-methoxy-2-methylquinoline

-butyl vinyl ether

p-anisidine hydrochloride

4-methoxy-aniline

Downstream raw materials:

(E)-6-methoxy-2-styrylquinoline

(E)-6-methoxy-2-(4-methoxystyryl)quinoline

2-(3,4-dimethoxy-trans-styryl)-6-methoxy-quinoline

6-methoxyquinoline-2-carboxaldehyde

Refernces

• 1、 Tian, Jin-Miao,Yuan, Yong-Hai,Xie, Yu-Yang,Zhang, Shu-Yu,Ma, Wen-Qiang,Zhang, Fu-Min,Wang, Shao-Hua,Zhang, Xiao-Ming,Tu, Yong-Qiang. "Catalytic Asymmetric Cascade Using Spiro-Pyrrolidine Organocatalyst: Efficient Construction of Hydrophenanthridine Derivatives". . p. 6618 - 6621. Retrieved 2017.
• 2、 Xue, Yu,He, Xiaomeng,Yang, Taoyi,Wang, Yuxi,Liu, Zhenming,Zhang, Guisen,Wang, Yanxing,Wang, Kewei,Zhang, Liangren,Zhang, Lihe. "Discovery of fused heterocyclic carboxamide derivatives as novel α7-nAChR agonists: Synthesis, preliminary SAR and biological evaluation". . . Retrieved 2019.
• 3、 Jia, Xiaodong,Peng, Fangfang,Qing, Chang,Huo, Congde,Wang, Yaxin,Wang, Xicun. "Synthesis of 2,3-disubstituted quinolines from in situ generated imines and its enamine tautomer under radical cation induced conditions". . p. 4950 - 4952. Retrieved 2013.
• 4、 Deng, Guozhong,Wan, Nanwei,Qin, Lei,Cui, Baodong,An, Miao,Han, Wenyong,Chen, Yongzheng. "Deracemization of Phenyl-Substituted 2-Methyl-1,2,3,4-Tetrahydroquinolines by a Recombinant Monoamine Oxidase from Pseudomonas monteilii ZMU-T01". . p. 2374 - 2377. Retrieved 2018.
• 5、 Reynolds, Kristie A.,Young, David J.,Loughlin, Wendy A.. "Limitations of the two-phase doebner-miller reaction for the synthesis of quinolines". . p. 3645 - 3648. Retrieved 2010.
• 6、 Cocker,Turner. "-". . p. 143. Retrieved 1941.
• 7、 Kusama, Hiroyuki,Yamashita, Yuko,Narasaka, Koichi. "Synthesis of Quinolines via Intramolecular Cyclization of Benzylacetone Oxime Derivatives Catalyzed with Tetrabutylammonium Perrhenate(VII) and Trifluoromethanesulfonic Acid". . p. 5 - 6. Retrieved 1995.
• 8、 Kusama, Hiroyuki,Uchiyama, Katsuya,Yamashita, Yuko,Narasaka, Koichi. "Synthesis of Azaspirodienones via Intramolecular Cyclization of p-Hydroxybenzylacetone Oximes and Their Transformation into Quinolines". . p. 715 - 716. Retrieved 1995.
• 9、 Matsugi,Tabusa,Minamikawa. "Doebner-miller synthesis in a two-phase system: Practical preparation of quinolines". . p. 8523 - 8525. Retrieved 2000.
• 10、 Song,Mertzman,Hughes. "Improved synthesis of quinaldines by the Skraup reaction". . p. 17 - 21. Retrieved 1993.