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

Base Information

• Chemical Name: 1,2,3,4-Tetrahydroisoquinolin-6-ol
• CAS No.: 14446-24-3
• Molecular Formula: C9H11NO
• Molecular Weight: 149.192
• Hs Code.: 2933499090
• European Community (EC) Number: 814-570-0
• UNII: 6WR7DU65P7
• DSSTox Substance ID: DTXSID80162711
• Nikkaji Number: J678.942K
• Wikidata: Q72505929
• ChEMBL ID: CHEMBL310736
• Mol file: 14446-24-3.mol

Synonyms:14446-24-3;1,2,3,4-tetrahydroisoquinolin-6-ol;6-Hydroxy-1,2,3,4-tetrahydroisoquinoline;1,2,3,4-Tetrahydro-isoquinolin-6-ol;1,2,3,4-Tetrahydro-6-isoquinolinol;6-ISOQUINOLINOL, 1,2,3,4-TETRAHYDRO-;BRN 0127578;CHEMBL310736;MFCD01717047;6-Hydroxytetrahydroisochinolin;6WR7DU65P7;SCHEMBL1017452;AMY3837;DTXSID80162711;CS-M3291;BDBM50024822;AKOS006333936;AB09835;AC-28820;LS-86170;SY003117;6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline;FT-0646913;H1572;EN300-96853;Q-102330;Z3018438111;1,2,3,4-Tetrahydroisoquinolin-6-ol

Chemical Property of 1,2,3,4-Tetrahydroisoquinolin-6-ol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 192-193℃
• Refractive Index: 1.582
• Boiling Point: 313.5 °C at 760 mmHg
• PKA: 9.30±0.20(Predicted)
• Flash Point: 169.5 °C
• PSA: 32.26000
• Density: 1.141 g/cm³
• LogP: 1.36670
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 149.084063974
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

1,2,3,4-Tetrahydroisoquinolin-6-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCC2=C1C=C(C=C2)O
• Uses: 1,2,3,4-Tetrahydroisoquinolin-6-ol is a chemical reagent used in the organic synthesis. Used in the preparation of androgen receptor modulators (SARMs) as well as steroidmimetic and chimeric microtubule disruptors.

Technology Process of 1,2,3,4-Tetrahydroisoquinolin-6-ol

There total 9 articles about 1,2,3,4-Tetrahydroisoquinolin-6-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 10.0%

6-methoxy-1,2,3,4-tetrahydro-isoquinoline (42923-77-3) → 6-hydroxy-1,2,3,4-tetrahydroisoquinoline (14446-24-3)

Guidance literature:

With hydrogen bromide; at 120 ℃; for 3h;

DOI:10.1016/j.bmc.2008.05.006

Reference yield:

6-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (63905-73-7) → 6-hydroxy-1,2,3,4-tetrahydroisoquinoline (14446-24-3)

Guidance literature:

6-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride; With sodium hydroxide; In 1,4-dioxane; water; at -5 ℃;

With hydrogenchloride; In 1,4-dioxane; water; pH=9;

Reference yield:

norfenefrine (536-21-0) → 6-hydroxy-1,2,3,4-tetrahydroisoquinoline (14446-24-3)

Guidance literature:

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

With hydrogen; palladium on activated charcoal; In hydrogenchloride; water;

DOI:10.1021/jo00365a041

upstream raw materials:

6-methoxy-1,2,3,4-tetrahydro-isoquinoline

formaldehyd

3-hydroxyphenylethylamine hydrochloride

norfenefrine

Downstream raw materials:

6-trifluoromethanesulfonyloxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

(S)-isopropyl6-(1-(2-fluoro-4-(methylsulfonyl)phenyl)pyrrolidin-3-yloxy)-3,4-dihydroisoquinorine-2(1H)-carboxylate

(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

Refernces

• 1、 Jing, Dong,Lu, Cong,Chen, Zhuo,Jin, Songyang,Xie, Lijuan,Meng, Ziyi,Su, Zhishan,Zheng, Ke. "Light-Driven Intramolecular C?N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex". supporting information. p. 14666 - 14672. Retrieved 2019/09/06.
• 2、 -. "COMPOUNDS AND COMPOSITIONS AS MODULATORS OF GPR119 ACTIVITY". Page/Page column 24-25. . Retrieved 2009/10/18.