• Name

  (S)-1,2,3,4-tetrahydro-6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)isoquinolinium chloride

• EINECS 242-423-5
• CAS No. 18559-59-6
• Article Data3
• CAS DataBase
• Density 1.235g/cm³
• Solubility
• Melting Point
• Formula C19H23 N O5 . Cl H
• Boiling Point 533.3°Cat760mmHg
• Molecular Weight 381.856
• Flash Point 276.3°C
• Transport Information
• Appearance
• Safety Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion and subcutaneous routes. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NO_x and HCl.
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 6,7-Isoquinolinediol,1,2,3,4-tetrahydro-1-(3,4,5-trimethoxybenzyl)-, hydrochloride, (-)- (8CI);6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-[(3,4,5-trimethoxyphenyl)methyl]-,hydrochloride, (1S)- (9CI); 6,7-Isoquinolinediol,1,2,3,4-tetrahydro-1-[(3,4,5-trimethoxyphenyl)methyl]-, hydrochloride, (S)-; (-)-Trimethoquinol;(-)-Trimetoquinol; AQL 208; Bentomex; Inolin; NSC 288748; Trimethoquinol;Trimetoquinol; Trimetoquinol hydrochloride; Triquinol; Vems; l-Trimetoquinol
• PSA 80.18000
• LogP 3.68390

Synthetic route

(S)-6,7-Bis(benzyloxy)-1-<(3,4,5-trimethoxyphenyl)methyl>-1,2,3,4-tetrahydroisoquinoline hydrochloride

18559-59-6

(-)-Trimetoquinol hydrochloride

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 50℃; under 3040 Torr; for 16h;	96%

(1S,1'S)-6,7-dibenzyloxy-2-(2-hydroxy-1-phenylethyl)-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

18559-59-6

(-)-Trimetoquinol hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol	86%

(3S)-8,9-dibenzyloxy-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo-<2,3-a>isoquinoline

18559-59-6

(-)-Trimetoquinol hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 86 percent / H2, 10percent HCl / 10percent Pd-C / ethanol View Scheme

3840-30-0

5-(chloromethyl)-1,2,3-trimethoxybenzene

18559-59-6

(-)-Trimetoquinol hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 86 percent / H2, 10percent HCl / 10percent Pd-C / ethanol View Scheme

N-(2-nitrophenylsulfenyl)-β-(3-hydroxy-4-(methoxymethoxy)phenyl)ethylamine

A

18559-59-6

(-)-Trimetoquinol hydrochloride

B

(+)-Trimetoquinol hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium sulfate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 80 °C / Inert atmosphere 2: hydrogenchloride / ethanol; water; dichloromethane / 24 h / 20 °C View Scheme

65299-00-5

3-hydroxy-4-(methoxymethoxy)benzaldehyde

A

18559-59-6

(-)-Trimetoquinol hydrochloride

B

(+)-Trimetoquinol hydrochloride

Conditions

Conditions

Yield

Multi-step reaction with 5 steps 1: ammonium acetate / 1 h / Molecular sieve; Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux 3: triethylamine; potassium carbonate / water; chloroform; methanol / 2 h / 0 °C 4: magnesium sulfate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 80 °C / Inert atmosphere 5: hydrogenchloride / ethanol; water; dichloromethane / 24 h / 20 °C View Scheme

139-85-5

3,4-dihydroxybenzaldehyde

A

18559-59-6

(-)-Trimetoquinol hydrochloride

B

(+)-Trimetoquinol hydrochloride

Conditions

Conditions

Yield

Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile / 0.5 h / 20 °C 1.2: 2 h 2.1: ammonium acetate / 1 h / Molecular sieve; Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux 4.1: triethylamine; potassium carbonate / water; chloroform; methanol / 2 h / 0 °C 5.1: magnesium sulfate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 80 °C / Inert atmosphere 6.1: hydrogenchloride / ethanol; water; dichloromethane / 24 h / 20 °C View Scheme

C27H30N2O8S

A

18559-59-6

(-)-Trimetoquinol hydrochloride

B

(+)-Trimetoquinol hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; dichloromethane; water at 20℃; for 24h; Overall yield = 86 %; Overall yield = 62 mg;

(E)-3-hydroxy-4-(methoxymethoxy)-1-(2-nitrovinyl)benzene

A

18559-59-6

(-)-Trimetoquinol hydrochloride

B

(+)-Trimetoquinol hydrochloride

Conditions

Conditions

Yield

Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux 2: triethylamine; potassium carbonate / water; chloroform; methanol / 2 h / 0 °C 3: magnesium sulfate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 80 °C / Inert atmosphere 4: hydrogenchloride / ethanol; water; dichloromethane / 24 h / 20 °C View Scheme

β-(3-hydroxy-4-(methoxymethoxy)phenyl)ethylamine

A

18559-59-6

(-)-Trimetoquinol hydrochloride

B

(+)-Trimetoquinol hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine; potassium carbonate / water; chloroform; methanol / 2 h / 0 °C 2: magnesium sulfate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 80 °C / Inert atmosphere 3: hydrogenchloride / ethanol; water; dichloromethane / 24 h / 20 °C View Scheme

Trimetoquinol hydrochloride Chemical Properties

Trimetoquinol hydrochloride Toxicity Data With Reference

Trimetoquinol hydrochloride Safety Profile