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2328-12-3

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Basic Information
CAS No.: 2328-12-3
Name: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride
Article Data: 15
Molecular Structure:
Molecular Structure of 2328-12-3 (6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride)
Formula: C11H16ClNO2
Molecular Weight: 229.707
Synonyms: Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-, hydrochloride (7CI,8CI,9CI);1,2,3,4-Tetrahydro-6,7-dimethoxyisoquinolinehydrochloride;6,7-Bis(methyloxy)-1,2,3,4-tetrahydroisoquinoline hydrochloride;Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-, hydrochloride (1:1);6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride;6,7-Dimethoxy-3,4-dihydro-2(1H)-isoquinolinehydrochloride;Heliamine hydrochloride;
EINECS: 251-223-7
Density: 1.071g/cm3
Melting Point: 260-265 °C(lit.)
Boiling Point: 314.9 °C at 760 mmHg
Flash Point: 124.7 °C
Appearance: white to slightly beige shiny flakes
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 30.49000
LogP: 2.48030
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Synthetic route
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Dimethoxymethane

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2-(3,4-dimethoxyphenyl)-ethylamine

2328-12-3

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water for 8h; Heating;88%
50-00-0

formaldehyd

120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

2328-12-3

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol Pictet-Spengler reaction;68.7%
Stage #1: formaldehyd; 2-(3,4-dimethoxyphenyl)-ethylamine In ethanol at 20℃; for 3h;
Stage #2: With hydrogenchloride In ethanol; water for 4h; pH=2; Reflux;		61.8%
Stage #1: formaldehyd; 2-(3,4-dimethoxyphenyl)-ethylamine In ethanol at 20℃; for 3h;
Stage #2: With hydrogenchloride In ethanol; water at 78℃; for 4h; pH=2;		61.8%
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bis(N-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolinyl)methane

2328-12-3

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 20℃; for 18h;
7647-01-0

hydrogenchloride

14429-07-3

C9H7(OCH3)2NBH3

A

1333-74-0

hydrogen

B

2328-12-3

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride

Conditions
ConditionsYield
In ethanol; water addn. of 5% aq. HCl to the ethanol soln. (cooling, stirring), stirring for 30min, refluxing for 30min;;
...Expand
2328-12-3

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride

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6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide

Conditions
ConditionsYield
With hydrogen bromide at 120℃; for 2h;100%
With hydrogen bromide at 105℃; for 5h;100%
With water; hydrogen bromide for 5h; Heating / reflux;100%
2328-12-3

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride

860436-60-8

5,8-dichloro-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Conditions
ConditionsYield
With sulfuryl dichloride In acetic acid at 20℃; for 3h;100%
With sulfuryl dichloride In acetic acid at 20℃; for 3h;100%
With sulfuryl dichloride In acetic acid at 20℃; for 4h;100%
With sulfuryl dichloride; acetic acid at 20℃; for 3h;100%
With sulfuryl dichloride In acetic acid at 20℃; for 0.5h; Product distribution / selectivity;
50-00-0

formaldehyd

2328-12-3

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride

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2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
Stage #1: 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride With sodium hydroxide In methanol for 0.333333h;
Stage #2: formaldehyd In methanol; water for 0.583333h;
Stage #3: With sodium tetrahydroborate In methanol; water		100%
Stage #1: formaldehyd; 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride With sodium methylate In methanol; water for 0.916667h; Inert atmosphere;
Stage #2: With sodium tetrahydroborate In methanol; water at 20℃; for 3h; Inert atmosphere;		90%
Stage #1: 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride With sodium hydroxide In dichloromethane; water Inert atmosphere;
Stage #2: formaldehyd With formic acid In water at 100℃; Inert atmosphere;		80%
75-44-5

phosgene

2328-12-3

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride

463-72-9

carbamic chloride

Conditions
ConditionsYield
In toluene99%
2328-12-3

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride

5-bromo-2-furanyl chloride

5-bromo-2-(2'-H-3,4-dihydro-6,7-methoxyisoquinoline)furan-2-carboxamide

Conditions
ConditionsYield
Stage #1: 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride With sodium hydroxide In dichloromethane; water at 0℃; for 0.5h;
Stage #2: 5-bromo-2-furanyl chloride In dichloromethane at 0 - 25℃;		99%

3-chloro-1-(2,4-dimethoxyphenyl)acetone

2328-12-3

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride

3-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-1-(2,4-dimethoxyphenyl)propan-1-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 6h;97.7%
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    ProName: High purity 6,7-Dimethoxy-1,2,3,4-tetr... CasNo: 2328-12-3 Molecular Formula: C11H16ClNO2 Appearance: white to slightly beige shiny flakes Application: Pharmaceutical Intermediate DeliveryTime: within in 5-7 working days after recei..

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Chemistry

Molecule structure of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (CAS NO.2328-12-3):

IUPAC Name: 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride 
Molecular Weight: 229.70324 g/mol
Molecular Formula: C11H16ClNO2 
Melting Point: 260-265 °C(lit.)
Flash Point: 124.7 °C
Enthalpy of Vaporization: 55.61 kJ/mol
Boiling Point: 314.9 °C at 760 mmHg
Vapour Pressure: 0.000451 mmHg at 25 °C
H-Bond Donor: 2
H-Bond Acceptor: 3
Rotatable Bond Count: 2
Exact Mass: 229.086956
MonoIsotopic Mass: 229.086956
Topological Polar Surface Area: 30.5
Heavy Atom Count: 15
Canonical SMILES: COC1=C(C=C2CNCCC2=C1)OC.Cl
InChI: InChI=1S/C11H15NO2.ClH/c1-13-10-5-8-3-4-12-7-9(8)6-11(10)14-2;/h5-6,12H,3-4,7H2,1-2H3;1H
InChIKey: SHOWAGCIRTUYNA-UHFFFAOYSA-N
EINECS: 251-223-7
Product Categories: API intermediates;Building Blocks;Heterocyclic Building Blocks;Isoquinolines

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 272mg/kg (272mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)		 Yakugaku Zasshi. Journal of Pharmacy. Vol. 88, Pg. 1197, 1968.
 
mouse LDLo parenteral 160mg/kg (160mg/kg) BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Journal of Pharmacology and Experimental Therapeutics. Vol. 62, Pg. 165, 1938.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: NX5017980
Hazard Note: Irritant

Specification

 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (CAS NO.2328-12-3) is also named as 1,2,3,4-Tetrahydro-6,7-dimethoxyisoquinoline hydrochloride ; Heliamine hydrochloride ; Isoquinoline, 6,7-dimethoxy-1,2,3,4-tetrahydro-, hydrochloride ; NSC 18443 . 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (CAS NO.2328-12-3) is white to slightly beige shiny flakes.