1,2,3,4-Tetrahydroisoquinoline-3-methanol Chemical Properties

Melting point:

180-182?C

Boiling point:

83-85 °C(Press: 0.3 Torr)

Density 

1.081±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

soluble in Dichloromethane

form 

Crystalline

pka

14.57±0.10(Predicted)

Appearance

light yellow solid

Water Solubility 

Soluble in dichloromethane. Slightly soluble in water.

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

HS Code 

2933499090

1,2,3,4-Tetrahydroisoquinoline-3-methanol Usage And Synthesis

Chemical Properties

Light Orange Solid

Uses

rac 1,2,3,4-Tetrahydroisoquinoline-3-methanol (cas# 63006-93-9) is a compound useful in organic synthesis.

Synthesis

GENERAL STEPS: The synthesis was modified with reference 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 reaction progress 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 (4) as a yellow crystalline solid in a yield of 2.09 g (98% yield, melting point 95-97 °C). The specific optical rotation of the product was in agreement with that reported in the 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

1,2,3,4-Tetrahydroisoquinoline-3-methanol(63006-93-9)Related Product Information

• Isoquinoline
• Methyl tetrahydrophthalic anhydride
• Tetramethylammonium hydroxide pentahydrate
• Methanol
• Tetrahydrothiophene
• cis-1,2,3,6-Tetrahydrophthalic anhydride
• 1,2,3,4-TETRAHYDROISOQUINOLINE
• 1,2,3,4-Tetrahydroquinoline
• Tetramethylammonium hydroxide
• Tetrabutylammonium hydroxide
• 1,1,3,3-Tetramethyldisiloxane
• Tetrakis(hydroxymethyl)phosphonium sulfate
• Tetrahydrofuran
• DELTA9-TETRAHYDROCANNABINOL
• (S)-(-)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL,(S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL
• 5,6,7,8-TETRAHYDROISOQUINOLINE
• (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL,(S)-(-)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL
• 1,2,3,4-Tetrahydroisoquinoline-3-methanol