1-ETHYL-1,2,3,4-TETRA-HYDRO-ISOQUINOLINE

Base Information

• Chemical Name: 1-ETHYL-1,2,3,4-TETRA-HYDRO-ISOQUINOLINE
• CAS No.: 25939-81-5
• Molecular Formula: C11H15N
• Molecular Weight: 161.247
• Hs Code.: 2933499090
• Mol file: 25939-81-5.mol

Synonyms:1-Ethyl-1,2,3,4-tetrahydroisoquinoline;

Chemical Property of 1-ETHYL-1,2,3,4-TETRA-HYDRO-ISOQUINOLINE

Chemical Property:

• Vapor Pressure: 0.0146mmHg at 25°C
• Refractive Index: 1.513
• Boiling Point: 257.4 °C at 760 mmHg
• PKA: 9.73±0.40(Predicted)
• Flash Point: 111.1 °C
• PSA: 12.03000
• Density: 0.949 g/cm³
• LogP: 2.61220
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98%min ^*data from raw suppliers

1-Ethyl-1,2,3,4-tetrahydroisoquinoline 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-ETHYL-1,2,3,4-TETRA-HYDRO-ISOQUINOLINE

There total 3 articles about 1-ETHYL-1,2,3,4-TETRA-HYDRO-ISOQUINOLINE 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: 53.0%

3,4-dihydro-isoquinoline 2-oxide (24423-87-8,65194-03-8) + diethylzinc (557-20-0) + 3,5-dimethoxyphenylboronic acid pinacol ester (365564-07-4) → 1-ethyl-1,2,3,4-tetrahydroisoquinoline (25939-81-5) + C17H19NO3 (1229227-19-3)

Guidance literature:

3,5-dimethoxyphenylboronic acid pinacol ester; With diethylzinc; In toluene; at 70 ℃; for 12h; Inert atmosphere;

3,4-dihydro-isoquinoline 2-oxide; diethylzinc; With [(1S)-1-((S)-1-methylpropyl)-(2-morpholin-4-ylethyl)]carbamic acid tert-butyl ester; In dichloromethane; toluene; at -30 - -20 ℃; for 24.25h; Inert atmosphere;

With methanol; In dichloromethane; toluene; at -20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol1004356

Reference yield: 35.0%

3,4-dihydro-isoquinoline 2-oxide (24423-87-8,65194-03-8) + t-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl carbonate (480438-75-3) + diethylzinc (557-20-0) → 1-ethyl-1,2,3,4-tetrahydroisoquinoline (25939-81-5) + C20H23NO4 (1229227-17-1)

Guidance literature:

t-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl carbonate; With diethylzinc; In toluene; at 70 ℃; for 12h; Inert atmosphere;

3,4-dihydro-isoquinoline 2-oxide; diethylzinc; With [(1S)-1-((S)-1-methylpropyl)-(2-morpholin-4-ylethyl)]carbamic acid tert-butyl ester; In dichloromethane; toluene; at -30 - -20 ℃; for 24.25h; Inert atmosphere;

With methanol; In dichloromethane; toluene; at -20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol1004356

Reference yield:

2-(2-bromoethyl)benzaldehyde (22901-09-3) → 1-ethyl-1,2,3,4-tetrahydroisoquinoline (25939-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; ammonia

2: tetrahydrofuran; benzene

With tetrahydrofuran; methanol; ammonia; benzene;

upstream raw materials:

2-(2-bromoethyl)benzaldehyde

3,4-dihydro-isoquinoline 2-oxide

t-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl carbonate

diethylzinc

Refernces