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Tetrahydroisoquinoline

Tetrahydroisoquinoline

Other names	1,2,3,4-Tetrahydroisoquinoline
Identifiers
CAS number	91-21-4
RTECS number	NX4900000
SMILES	c1ccc2CCNCc2c1
Properties
Molecular formula	C₉H₁₁N
Molar mass	133.19 g/mol
Appearance	Deep yellow liquid
Density	1.05 g/mL
Melting point	-30 °C
Boiling point	235-239 °C
Hazards
EU classification	Irritant (Xi)
R-phrases	R36/37/38
S-phrases	S26 S36
Flash point	99 °C (closed cup)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Tetrahydroisoquinoline is a secondary amine with the chemical formula C₉H₁₁N.

Reactions

Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.^[1]

The tetrahydroisoquinoline skeleton is commonly encountered in quaternary ammonium muscle relaxants.

^ S.-I. Murahashi and T. Shiota (1987). "Selenium dioxide catalyzed oxidation of secondary amines with hydrogen peroxide. Simple synthesis of nitrones from secondary amines". Tetrahedron Letters 28 (21): 2383-2386. doi:10.1016/S0040-4039(00)96130-6.