1,2,3,4-Tetrahydroisoquinolin-6-ol supplier

Name
1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL
EINECS -0
CAS No. 14446-24-3
Article Data10
CAS DataBase
Density 1.141 g/cm³
Solubility
Melting Point 192-193℃
Formula C₉H₁₁NO
Boiling Point 313.5 °C at 760 mmHg
Molecular Weight 149.192
Flash Point 169.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,2,3,4-Tetrahydro-6-isoquinolinol;6-Hydroxy-1,2,3,4-tetrahydroisoquinoline;
PSA 32.26000
LogP 1.36670

Synthetic route

: 42923-77-3
6-methoxy-1,2,3,4-tetrahydro-isoquinoline

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With hydrogen bromide at 120℃; for 3h;	10%
With hydrogenchloride; water at 170℃;
With boron tribromide In methanol; dichloromethane

: 50-00-0
formaldehyd

: 3458-98-8
3-hydroxyphenylethylamine hydrochloride

A: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

B: 32999-37-4
1,2,3,4-tetrahydroisoquinoline-8-ol

Conditions

Conditions	Yield
In water at 20℃;
In water at 20℃; Product distribution; Mechanism; other 3-hydroxyphenethylamines, other aldehydes; var. pH;

...Expand

: 536-21-0
norfenefrine

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / H2 / 10percent Pd/C / aq. HCl / 30 h / 775.7 - 1810.02 Torr 2: H2O / 20 °C / other 3-hydroxyphenethylamines, other aldehydes; var. pH View Scheme

: 2039-67-0
2-(3-methoxyphenyl)-1-ethanamine

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrochloric acid; water 2: hydrochloric acid; water / 170 °C View Scheme

: 63905-73-7
6-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
Stage #1: 6-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride With sodium hydroxide In 1,4-dioxane; water at -5℃; Stage #2: With hydrogenchloride In 1,4-dioxane; water pH=9;

: 22245-98-3
6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 12h; Inert atmosphere; Reflux;

: C11H15NO3

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluorormethanesulfonic acid / 16 h / 20 - 70 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Inert atmosphere; Reflux View Scheme

: 588-05-6
m-tyramine

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 1 h / 0 - 25 °C 2: trifluorormethanesulfonic acid / 16 h / 20 - 70 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Inert atmosphere; Reflux View Scheme

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 24424-99-5
di-tert-butyl dicarbonate

: 158984-83-9
N-tert-butoxycarbonyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran; water at 20℃;	91%
With triethylamine In dichloromethane at 0 - 20℃; for 12h;	80%
With triethylamine In methanol at 20℃;	66%

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 78485-37-7
6-aethoxycarbonyl-2-chlorbenzothiazol

: ethyl 2-(6-hydroxy-3,4-dihydroisoquinolin-2(1H)-yl)benzo[d]thiazole-6-carboxylate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 100℃; for 1h;	84%

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 814-68-6
acryloyl chloride

: N-acryloyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
Stage #1: 6-hydroxy-1,2,3,4-tetrahydroisoquinoline With triethylamine In dichloromethane at 25℃; for 0.5h; Stage #2: acryloyl chloride In dichloromethane at 0 - 25℃;	79%

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 104-15-4
toluene-4-sulfonic acid

: 1609545-55-2
C9H9Cl2NO*C7H8O3S

Conditions

Conditions	Yield
With N-chloro-succinimide In acetonitrile at 20℃;	61%

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 345649-43-6
(2RS,4SR)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl methanesulfonate

: 1667-11-4
biphenyl-4-methylchloride

: 6-[(2RS,4SR)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyloxy]-2-(4-phenylbenzyl)-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With potassium carbonate In N-methyl-acetamide; methanol; dichloromethane; water; ethyl acetate	57%

...Expand

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 345649-43-6
(2RS,4SR)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl methanesulfonate

: Cis (+/-)6-[[2-(2,4dichlorophenyl)-2-(1H-imidazol-1-yl-methyl)-1,3-dioxolan-4-yl]-methoxy]-1,2,3,4-tetrahydro-isoquinoline

Conditions

Conditions	Yield
In methanol; dichloromethane; water; dimethyl sulfoxide	53%

: 5344-90-1
2-Aminobenzyl alcohol

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 3-hydroxy-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-one

Conditions

Conditions	Yield
With oxygen; 4-nitro-benzoic acid In para-xylene at 120℃; for 16h; chemoselective reaction;	51%

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 191013-68-0
3-(3-Bromopropyl)-5-fluoro-1H-indole

: 1045805-48-8
2-[3-(5-fluoro-1H-indol-3-yl)-propyl]-6-hydroxy-1,2,3,4-tetrahydro-isoquinoline

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 100℃; for 24h;	48%

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 88-10-8
N,N-diethylcarbamyl chloride

: C14H20N2O2

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 12h;	48%

: 137-43-9
Cyclopentyl bromide

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 6-(cyclopentyloxy)-3,4-dihydroisoquinoline-2(1H)-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 100h;	1%

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 431-47-0
trifluoroacetic acid-methyl ester

: 216064-45-8
2-(trifluoroacetyl)-1,2,3,4-tetrahydro-6-isoquinolinol

Conditions

Conditions	Yield
In N,N-dimethyl-formamide

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 42908-86-1
2-Chloromethylbenzoyl chloride

: 7515-38-0
(E)-4-phenylbut-3-en-1-amine

: 2-(6-hydroxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-N-(4-phenyl-but-3-enyl)-benzamide

Conditions

Conditions	Yield
Multistep reaction;

...Expand

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 54893-54-8
6‐methoxy‐N‐methyl‐1,2,3,4‐tetrahydroisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: dimethylformamide 2: p-TsOH*H2O / CH2Cl2 3: aq NaOH / dioxane View Scheme

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 59529-93-0
6-ethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: dimethylformamide 2: p-TsOH*H2O / CH2Cl2 3: aq NaOH / dioxane View Scheme

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 6-Isobutoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: dimethylformamide 2: p-TsOH*H2O / CH2Cl2 3: aq NaOH / dioxane View Scheme

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 6-[((E)-But-2-enyl)oxy]-2-methyl-1,2,3,4-tetrahydro-isoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: dimethylformamide 2: p-TsOH*H2O / CH2Cl2 3: aq NaOH / dioxane View Scheme

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 200396-68-5
6-(tetrahydropyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dimethylformamide 2: p-TsOH*H2O / CH2Cl2 3: aq NaOH / dioxane View Scheme

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 2-methyl-6-(4-phenylbutoxy)-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: dimethylformamide 2: p-TsOH*H2O / CH2Cl2 3: aq NaOH / dioxane View Scheme

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 216064-47-0
6-(tetrahydropyran-2-yloxy)-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide 2: p-TsOH*H2O / CH2Cl2 View Scheme

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 32247-96-4
3,5-bis(trifluoromethyl)benzyl bromide

: 2-(3,5-bis-trifluoromethyl-benzyl)-1,2,3,4-tetrahydro-isoquinolin-6-ol

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 16h;

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 103979-29-9
(E)-1-(4-chlorophenyl)-3-chloropropene

: 263395-26-2
(E)-2-[3-(4-chlorophenyl)-2-propenyl]-1,2,3,4-tetrahydro-6-isoquinolinol

Conditions

Conditions	Yield
With potassium carbonate In dichloromethane; water; N,N-dimethyl-formamide

: 98-03-3
thiophene-2-carbaldehyde

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: toluenesulfonic acid monohydrate

: 6-Hydroxy-2-(thien-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With sodium cyanoborohydride In ethanol; dichloromethane; ethyl acetate

...Expand

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 109-89-7
diethylamine

: 75-36-5
acetyl chloride

: 59839-29-1
1-(6-hydroxy-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one

Conditions

Conditions	Yield
With acetic anhydride; triethylamine In methanol; ethanol; ethyl acetate

...Expand

: 14446-24-3
6-hydroxy-1,2,3,4-tetrahydroisoquinoline

: 122-01-0
4-chloro-benzoyl chloride

: 6-Hydroxy-2-(4-chlorobenzoyl)-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With hydrogenchloride; triethylamine In dichloromethane

1,2,3,4-Tetrahydroisoquinolin-6-ol Chemical Properties

Molecular structure of 6-Isoquinolinol, 1,2,3,4-tetrahydro- (CAS NO.14446-24-3) is:

Product Name: 6-Isoquinolinol, 1,2,3,4-tetrahydro-
CAS Registry Number: 14446-24-3
IUPAC Name: 1,2,3,4-tetrahydroisoquinolin-6-ol
Molecular Weight: 149.18974 [g/mol]
Molecular Formula: C₉H₁₁NO
XLogP3-AA: 1
H-Bond Donor: 2
H-Bond Acceptor: 2
Canonical SMILES: C1CNCC2=C1C=C(C=C2)O
InChI: InChI=1S/C9H11NO/c11-9-2-1-8-6-10-4-3-7(8)5-9/h1-2,5,10-11H,3-4,6H2
InChIKey: SCMZIFSYPJICCV-UHFFFAOYSA-N
Surface Tension: 46.4 dyne/cm
Density: 1.141 g/cm³
Flash Point: 169.5 °C
Enthalpy of Vaporization: 57.66 kJ/mol
Boiling Point: 313.5 °C at 760 mmHg
Vapour Pressure: 0.000269 mmHg at 25°C
Classification Code: Drug / Therapeutic Agent
Product Categories: API intermediates

1,2,3,4-Tetrahydroisoquinolin-6-ol Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LDLo	subcutaneous	480mg/kg (480mg/kg)	AUTONOMIC NERVOUS SYSTEM: SYMPATHOMIMETIC	"Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 244, 1948.

1,2,3,4-Tetrahydroisoquinolin-6-ol Specification

6-Isoquinolinol, 1,2,3,4-tetrahydro- , its cas register number is 14446-24-3. It also can be called 1,2,3,4-Tetrahydro-6-isoquinolinol ; 5-21-02-00326 (Beilstein Handbook Reference) ; BRN 0127578 .

Product Name

1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL

Synthetic route

1,2,3,4-Tetrahydroisoquinolin-6-ol Chemical Properties

1,2,3,4-Tetrahydroisoquinolin-6-ol Toxicity Data With Reference

1,2,3,4-Tetrahydroisoquinolin-6-ol Specification

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