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Name	1,2,3,4-Tetrahydroisoquinolin-6-ol	EINECS	-0
CAS No.	14446-24-3	Density	1.141 g/cm³
PSA	32.26000	LogP	1.36670
Solubility	N/A	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	N/A	Appearance	N/A
Safety		Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	1,2,3,4-Tetrahydro-6-isoquinolinol;6-Hydroxy-1,2,3,4-tetrahydroisoquinoline;	Article Data	10

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

: 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%

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 .

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