1,2,3,4-Tetrahydroisoquinolin-5-ol

Base Information

• Chemical Name: 1,2,3,4-Tetrahydroisoquinolin-5-ol
• CAS No.: 102877-50-9
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.192
• Hs Code.: 2933499090
• ChEMBL ID: CHEMBL308021
• DSSTox Substance ID: DTXSID00553061
• Wikidata: Q72505932
• Mol file: 102877-50-9.mol

Synonyms:1,2,3,4-Tetrahydroisoquinolin-5-ol;102877-50-9;1,2,3,4-Tetrahydro-isoquinolin-5-ol;5-Hydroxy-1,2,3,4-tetrahydroisoquinoline;CHEMBL308021;1,2,3,4-Tetrahydro-5-isoquinolinol Acetate;164653-60-5;1,2,3,4-tetrahydro-5-Isoquinolinol;SCHEMBL1956718;AMY4266;DTXSID00553061;OMZHCCXUVSEGAD-UHFFFAOYSA-N;CEA87750;BDBM50024824;MFCD06656937;AKOS006343050;CS-W006334;SB30264;5-hydroxy-3,4-dihydro-1H-isoquinoline;LS-10098;A26324;EN300-120936

Chemical Property of 1,2,3,4-Tetrahydroisoquinolin-5-ol

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 273 °C
• Refractive Index: 1.582
• Boiling Point: 294.3 °C at 760 mmHg
• PKA: 9.30±0.20(Predicted)
• Flash Point: 153.6 °C
• PSA: 32.26000
• Density: 1.141 g/cm³
• LogP: 1.36670
• Storage Temp.: Sealed in dry,Store in freezer, under -20°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:

98%,99%, ^*data from raw suppliers

1,2,3,4-Tetrahydroisoquinolin-5-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCC2=C1C(=CC=C2)O
• Uses: 1,2,3,4-Tetrahydroisoquinolin-5-ol is a reagent used in the preparation of potent and selective inhibitors of type 5 17-B-Hydroxysteroid dehydrogenase AKR1C3.

Technology Process of 1,2,3,4-Tetrahydroisoquinolin-5-ol

There total 6 articles about 1,2,3,4-Tetrahydroisoquinolin-5-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: 93.0%

5-hydroxyisoquinoline (2439-04-5) → 1,2,3,4-tetrahydro-5-hydroxy-isoquinoline (102877-50-9)

Guidance literature:

With hydrogen; platinum(IV) oxide; In acetic acid; at 20 ℃; for 16h; under 2250.18 Torr;

DOI:10.1016/j.tet.2006.04.095

Reference yield:

1,2,3,4-tetrahydroisoquinolin-5-amine (115955-90-3) → 1,2,3,4-tetrahydro-5-hydroxy-isoquinoline (102877-50-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium nitrite; sulfuric acid / water

2: hydrogen; palladium on activated charcoal

With sulfuric acid; palladium on activated charcoal; hydrogen; sodium nitrite; In water;

DOI:10.1016/j.bmcl.2013.10.009

Reference yield:

isoquinoline (119-65-3) → 1,2,3,4-tetrahydro-5-hydroxy-isoquinoline (102877-50-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / 5 h / 120 °C

2: sodium hydroxide / water / 24 h / Reflux

3: sodium cyanoborohydride / acetic acid / 6 h / Reflux

With sulfuric acid; sodium cyanoborohydride; sodium hydroxide; In water; acetic acid;

upstream raw materials:

5-hydroxyisoquinoline

1,2,3,4-tetrahydroisoquinolin-5-amine

isoquinoline

isoquinoline-5-sulfonic acid

Downstream raw materials:

5-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline

5-Hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

2-Acetyl-5-hydroxy-1,2,3,4-tetrahydro-isochinolin

C₁₆H₁₅NO₅S

Refernces

• 1、 Fray, M. Jonathan,Allen, Paul,Bradley, Paul R.,Challenger, Clare E.,Closier, Michael,Evans, Tim J.,Lewis, Mark L.,Mathias, John P.,Nichols, Carly L.,Po-Ba, Yvonne M.,Snow, Hayley,Stefaniak, Mark H.,Vuong, Hannah V.. "Synthesis of substituted 5-aminomethyl tetrahydro-isoquinolines and dihydro-isoindoles". . p. 6869 - 6875. Retrieved 2006.
• 2、 -. "Preparation method of tetrahydroisoquinoline derivative". Paragraph 0025; 0026. . Retrieved 2018/03/24.