5,8-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: 5,8-Dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 76019-13-1
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.246
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID60226941
• Nikkaji Number: J395.228B
• Wikidata: Q83106527
• ChEMBL ID: CHEMBL284257
• Mol file: 76019-13-1.mol

Synonyms:5,6-dimethoxy-1,2,3,4-tetrahydroisoquinoline;SK and F 72223;SK and F-72223;SKF 72223

Chemical Property of 5,8-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

• Vapor Pressure: 3.62E-05mmHg at 25°C
• Boiling Point: 353.3°C at 760 mmHg
• Flash Point: 138.3°C
• PSA: 30.49000
• Density: 1.071g/cm³
• LogP: 1.67830
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 193.110278721
• Heavy Atom Count: 14
• Complexity: 186

Purity/Quality:

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

5,8-Dimethoxy-1,2,3,4-tetrahydroisoquinoline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C2CCNCC2=C(C=C1)OC

Technology Process of 5,8-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

There total 7 articles about 5,8-Dimethoxy-1,2,3,4-tetrahydroisoquinoline 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: 89.0%

2-formyl-1,2,3,4-tetrahydro-5,8-dimethoxyisoquinoline (212184-69-5) → 5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline (76019-13-1)

Guidance literature:

With sodium hydroxide; In ethanol; Ambient temperature;

DOI:10.1248/cpb.46.918

Reference yield:

2,5-dimethoxybenzaldehyde (93-02-7) → 5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline (76019-13-1)

Guidance literature:

Multi-step reaction with 7 steps

1: AcOH / ethanol / 18 h / Heating

2: NaBH₄ / methanol / 1 h / Ambient temperature

3: 96 percent / acetic anhydride / 1 h / 70 °C

4: 93 percent / NaIO₄ / H₂O; methanol / 16 h / Ambient temperature

5: 60 percent / TFAA / benzene / 151 h / Ambient temperature; other N-(aryl)methyl-2-(phenylsulfinyl)ethylamines, also with TFAA and BF₃*Et₂O

6: 64 percent / NaBH₄, NiCl₂*6H₂O / methanol; tetrahydrofuran / 0.5 h / Ambient temperature

7: 89 percent / 10percent aq. NaOH / ethanol / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; sodium periodate; acetic anhydride; acetic acid; trifluoroacetic anhydride; nickel dichloride; In tetrahydrofuran; methanol; ethanol; water; benzene;

DOI:10.1248/cpb.46.918

Reference yield:

[1-(2,5-Dimethoxy-phenyl)-meth-(Z)-ylidene]-(2-phenylsulfanyl-ethyl)-amine → 5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline (76019-13-1)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH₄ / methanol / 1 h / Ambient temperature

2: 96 percent / acetic anhydride / 1 h / 70 °C

3: 93 percent / NaIO₄ / H₂O; methanol / 16 h / Ambient temperature

4: 60 percent / TFAA / benzene / 151 h / Ambient temperature; other N-(aryl)methyl-2-(phenylsulfinyl)ethylamines, also with TFAA and BF₃*Et₂O

5: 64 percent / NaBH₄, NiCl₂*6H₂O / methanol; tetrahydrofuran / 0.5 h / Ambient temperature

6: 89 percent / 10percent aq. NaOH / ethanol / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; sodium periodate; acetic anhydride; trifluoroacetic anhydride; nickel dichloride; In tetrahydrofuran; methanol; ethanol; water; benzene;

DOI:10.1248/cpb.46.918

upstream raw materials:

2-formyl-1,2,3,4-tetrahydro-5,8-dimethoxyisoquinoline

2,5-dimethoxybenzaldehyde

(2,5-Dimethoxy-benzyl)-(2-phenylsulfanyl-ethyl)-amine

5,8-Dimethoxy-4-phenylsulfanyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde

Refernces