8-Methyl-1,2,3,4-tetrahydroquinoline Chemical Properties

Boiling point:

255 °C

Density 

0.990±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

liquid

pka

5.01±0.20(Predicted)

color 

Light brown

CAS DataBase Reference

52601-70-4

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

26-36/37/39-24/25

HS Code 

2933499090

8-Methyl-1,2,3,4-tetrahydroquinoline Usage And Synthesis

Uses

8-Methyl-1,2,3,4-tetrahydroquinoline is a useful reagent for template-directed meta-C-H activation.

Definition

ChEBI: 8-Methyl-1,2,3,4-tetrahydroquinoline is a member of quinolines.

Synthesis Reference(s)

The Journal of Organic Chemistry, 25, p. 463, 1960 DOI: 10.1021/jo01073a611

Synthesis

The general procedure for the synthesis of 8-methyl-1,2,3,4-tetrahydroquinoline from 8-methylquinoline is as follows: unlike the Suzuki-Miyaura coupling reaction, the Pd-pol catalyst exhibits truly non-homogeneous catalytic properties for the reduction of nitroaromatics in the aqueous phase (see Table 2) [46]. In addition, the catalyst can be used for the selective hydrogenation of quinoline derivatives in aqueous-phase media at a pressure of 10 bar H2 at a reaction temperature of 80 °C (cf. Table 3) [47] or at 60 °C with NaBH4 as a hydrogen source (cf. Table 4) [48].

References

[1] Molecules, 2015, vol. 20, # 10, p. 18661 - 18684
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 6, p. 933 - 940
[3] Chemical Communications, 2013, vol. 49, # 63, p. 7052 - 7054
[4] Advanced Synthesis and Catalysis, 2016, vol. 358, # 19, p. 3039 - 3045
[5] Patent: CN106831565, 2017, A. Location in patent: Paragraph 0079; 0080; 0081; 0082

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