(S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL Chemical Properties

Melting point:

114-116 °C(lit.)

Boiling point:

290.31°C (rough estimate)

Density 

1.0508 (rough estimate)

refractive index 

-97 ° (C=0.2, MeOH)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

14.57±0.10(Predicted)

form 

Crystalline Powder and/or Chunks

color 

Off-white

optical activity

[α]22/D 97°, c = 1 in methanol

CAS DataBase Reference

18881-17-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

(S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Synthesis

GENERAL STEPS: The experimental manipulation of this reaction was improved by referring to the literature [6]. LiAlH4 (1.98 g, 52.0 mmol) was suspended in anhydrous THF (100 mL) under nitrogen protection, stirred and cooled to 0 °C. Subsequently, a THF solution of methyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (2.50 g, 13.0 mmol) was added slowly and dropwise. The reaction mixture was stirred continuously for 3 h at 0 °C and the progress of the reaction was monitored by thin layer chromatography (TLC) with the unfolding agent being petroleum ether:ethyl acetate (70:30, Rf = 0.43). Upon completion of the reaction, saturated sodium sulfate solution (4 mL) and THF (20 mL) were slowly added to quench the excess LiAlH4 at 0 °C. The inorganic solids were removed by filtration, and the filter cake was washed with ethyl acetate (3 × 30 mL). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford (S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline as a yellow crystalline solid (yield: 2.09 g, 98% yield, melting point 95-97 °C). The specific optical rotation of the product was in agreement with that reported in literature [6].1H NMR (400 MHz, CDCl3) δ: 2.57 (dd, 1H, J = 10.8, 11.2 Hz), 2.70 (dd, 1H, J = 4.34, 16.42 Hz), 3.05-3.10 (m, 1H), 3.49 (dd, 1H, J = 8.17, 10.82 Hz), 3.78 (dd, 1H, J = 3.98, 10.60 Hz), 4.05 (s, 2H), 7.01-7.15 (m, 4H).13C NMR (100 MHz, CDCl3) δ: 135.6, 133.9, 129.3, 126.3, 126.0, 125.9, 65.8, 55.0 , 47.83, 30.9.

References

[1] South African Journal of Chemistry, 2010, vol. 63, p. 195 - 198
[2] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 407 - 414

(S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL(18881-17-9)Related Product Information

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