6-Methoxy-1,2,3,4-tetrahydroquinoline

Base Information

• Chemical Name: 6-Methoxy-1,2,3,4-tetrahydroquinoline
• CAS No.: 120-15-0
• Molecular Formula: C10H13 N O
• Molecular Weight: 163.219
• Hs Code.: 2933499090
• European Community (EC) Number: 204-374-8
• NSC Number: 49188
• UNII: EA6AYU7Y78
• DSSTox Substance ID: DTXSID3059505
• Nikkaji Number: J5.320A
• Wikidata: Q81988832
• Mol file: 120-15-0.mol

Synonyms:6-Methoxy-1,2,3,4-tetrahydroquinoline;120-15-0;Thallin;Thalline;6-Methoxy-1,2,3,4-tetrahydro-quinoline;Quinoline, 1,2,3,4-tetrahydro-6-methoxy-;6-Methoxytetrahydroquinoline;1,2,3,4-Tetrahydro-6-methoxyquinoline;EA6AYU7Y78;Methyl 1,2,3,4-tetrahydro-6-quinolyl ether;EINECS 204-374-8;MFCD00090494;NSC 49188;NSC-49188;Quinoline l,2,3,4-tetrahydro-6-methoxy;UNII-EA6AYU7Y78;Oprea1_399678;SCHEMBL665048;DTXSID3059505;HMS1704G06;AMY25898;NSC49188;WLN: T66 BMT & J HO1;STK500842;1,3,4-Tetrahydro-6-methoxyquinoline;6-Methoxy-1,3,4-tetrahydroquinoline;AKOS000123926;Quinoline l,3,4-tetrahydro-6-methoxy;CS-W000806;FS-5116;Quinoline,2,3,4-tetrahydro-6-methoxy-;SY106890;BB 0254226;FT-0631690;EN300-24247;6-Methoxy-1,2,3,4-tetrahydroquinoline, 99%;H10927;A804442;QUINOLINE,1,2,3,4-TETRAHYDRO-6-METHOXY-;J-004267;F9995-1237;Z169918896

Chemical Property of 6-Methoxy-1,2,3,4-tetrahydroquinoline

Chemical Property:

• Vapor Pressure: 0.000933mmHg at 25°C
• Melting Point: 37-41 °C(lit.)
• Refractive Index: 1.5718 (estimate)
• Boiling Point: 303.4 °C at 760 mmHg
• PKA: 5.95±0.20(Predicted)
• Flash Point: 116.5 °C
• PSA: 21.26000
• Density: 1.044 g/cm³
• LogP: 2.19130
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 163.099714038
• Heavy Atom Count: 12
• Complexity: 149

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Methoxy-1,2,3,4-tetrahydroquinoline ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)NCCC2
• Uses: 1,2,3,4-Tetrahydro-6-methoxyquinoline is used as chemical reagents, organic intermediates, fine chemicals, pharmaceutical research and development.

Technology Process of 6-Methoxy-1,2,3,4-tetrahydroquinoline

There total 27 articles about 6-Methoxy-1,2,3,4-tetrahydroquinoline 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%

6-methoxy quinoline (5263-87-6) → 6-methoxy-1,2,3,4-tetrahydroquinoline (120-15-0)

Guidance literature:

With hydrogen; platinum(IV) oxide; In methanol; for 12h; under 3102.89 Torr;

DOI:10.1016/j.bmcl.2006.04.004

Reference yield: 96.0%

6-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline (54197-64-7) → 6-methoxy-1,2,3,4-tetrahydroquinoline (120-15-0)

Guidance literature:

With [RuCl₂(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; hydrogen; caesium carbonate; In toluene; butan-1-ol; at 120 ℃; for 6h; under 22502.3 Torr; Schlenk technique; Autoclave;

DOI:10.1021/acs.orglett.9b03878

Reference yield: 91.0%

(2-amino-5-methoxyphenyl)methanol (55414-72-7) + ethanol (64-17-5) → 6-methoxy-1,2,3,4-tetrahydroquinoline (120-15-0)

Guidance literature:

With nanosized Ni particles supported on Ni- and Al-containing layered double oxides; at 120 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.1021/acscatal.9b03245

upstream raw materials:

6-methoxy quinoline

1-prenyl-6-methoxy-1,2,3,4-tetrahydroquinoline

1-E-crotyl-6-methoxy-1,2,3,4-tetrahydroquinoline

methyl iodide

Downstream raw materials:

6-hydroxy-1,2,3,4-tetrahydroquinoline

1-benzyl-6-methoxy-1,2,3,4-tetrahydroquinoline

6-methoxy-1,2,3,4-tetrahydroquinolin-3-ol

1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)prop-2-en-1-one

Refernces

• 1、 Cho, Hyejin,T?r?k, Fanni,T?r?k, Béla. "Selective reduction of condensed N-heterocycles using water as a solvent and a hydrogen source". . p. 1209 - 1215. Retrieved 2013.
• 2、 Fujita, Ken-Ichi,Kitatsuji, Chihiro,Furukawa, Shigetoyo,Yamaguchi, Ryohei. "Regio- and chemoselective transfer hydrogenation of quinolines catalyzed by a Cp*Ir complex". . p. 3215 - 3217. Retrieved 2004.
• 3、 Ren, Dong,He, Lin,Yu, Lei,Ding, Ran-Sheng,Liu, Yong-Mei,Cao, Yong,He, He-Yong,Fan, Kang-Nian. "An unusual chemoselective hydrogenation of quinoline compounds using supported gold catalysts". . p. 17592 - 17598,7. Retrieved 2012.
• 4、 Srikrishna, Adusumilli,Reddy, T. Jagadeeswar,Viswajanani, Ranganathan. "Reduction of quinolines to 1,2,3,4-tetrahydro derivatives employing a combination of NaCNBH3 and BF3.OEt2". . p. 1631 - 1636. Retrieved 1996.
• 5、 Zhang, Sai,Xia, Zhaoming,Ni, Ting,Zhang, Huan,Wu, Chao,Qu, Yongquan. "Tuning chemical compositions of bimetallic AuPd catalysts for selective catalytic hydrogenation of halogenated quinolines". . p. 3260 - 3266. Retrieved 2017.
• 6、 Shao, Fangjun,Yao, Zihao,Gao, Yijing,Zhou, Qiang,Bao, Zhikang,Zhuang, Guilin,Zhong, Xing,Wu, Chuan,Wei, Zhongzhe,Wang, Jianguo. "Geometric and electronic effects on the performance of a bifunctional Ru2P catalyst in the hydrogenation and acceptorless dehydrogenation of N-heteroarenes". . p. 1185 - 1194. Retrieved 2021.
• 7、 Niu, Mingming,Wang, Yanhua,Chen, Pu,Du, Dongjie,Jiang, Jingyang,Jin, Zilin. "Highly efficient and recyclable rhodium nanoparticle catalysts for hydrogenation of quinoline and its derivatives". . p. 4746 - 4749. Retrieved 2015.
• 8、 Zhang, Jian,An, Zhe,Zhu, Yanru,Shu, Xin,Song, Hongyan,Jiang, Yitao,Wang, Wenlong,Xiang, Xu,Xu, Linlin,He, Jing. "Ni0/Niδ+ Synergistic Catalysis on a Nanosized Ni Surface for Simultaneous Formation of C-C and C-N Bonds". . p. 11438 - 11446. Retrieved 2019.
• 9、 Ranu, Brindaban C.,Jana, Umasish,Sarkar, Arunkanti. "Regioselective reduction of quinolines and related systems to 1,2,3,4-tetrahydro derivatives with zinc borohydride". . p. 485 - 492. Retrieved 1998.
• 10、 Cao, Yueling,Chen, Kai-Jie,Liu, Kangkai,Zhang, Hepeng. "Water-assisted one-pot synthesis of N-doped carbon supported Ru catalysts for heterogeneous catalysis". . p. 11311 - 11314. Retrieved 2020.