1,2,3,4-Tetrahydroisoquinoline

Base Information

• Chemical Name: 1,2,3,4-Tetrahydroisoquinoline
• CAS No.: 91-21-4
• Molecular Formula: C9H11N
• Molecular Weight: 133.193
• Hs Code.: 29334900
• European Community (EC) Number: 202-050-0
• NSC Number: 15312
• UNII: 56W89FBX3E
• DSSTox Substance ID: DTXSID6026115
• Nikkaji Number: J4.337K
• Wikipedia: Tetrahydroisoquinoline
• Wikidata: Q411677
• Metabolomics Workbench ID: 42031
• ChEMBL ID: CHEMBL14346
• Mol file: 91-21-4.mol

Synonyms:1,2,3,4-tetrahydro-2-azanaphthalene;1,2,3,4-tetrahydroisoquinoline;3,4-dihydro-1H-isoquinoline;HCl of 1,2,3,4-tetrahydroisoquinoline;isoquinoline, 1,2,3,4-tetrahydro-;tetrahydroisoquinoline

Chemical Property of 1,2,3,4-Tetrahydroisoquinoline

Chemical Property:

• Appearance/Colour: clear yellow to brown liquid
• Vapor Pressure: 0.0588mmHg at 25°C
• Melting Point: -25 °C
• Refractive Index: n20/D 1.568(lit.)
• Boiling Point: 232.5 °C at 760 mmHg
• PKA: 9.66±0.20(Predicted)
• Flash Point: 98.9 °C
• PSA: 12.03000
• Density: 1.006 g/cm³
• LogP: 1.66110
• Storage Temp.: Store below +30°C.
• Solubility.: 20g/l
• Water Solubility.: Soluble in water at 20°C 20g/L.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 133.089149355
• Heavy Atom Count: 10
• Complexity: 111

Purity/Quality:

99% ^*data from raw suppliers

1,2,3,4-Tetrahydroisoquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Quinolines
• Canonical SMILES: C1CNCC2=CC=CC=C21
• Description: 1, 2, 3, 4-TETRAHYDROISOQUINOLINE belongs to tetrahydroisoquinoline compound, which is encountered in a number of drugs, tubocurarine, one of the quaternary ammonium muscle relaxants1-3. It is used as a reagent in the preparation of4-(1, 2, 4-oxadiazol-5-yl) piperidine-1-carboxamides as antiproliferative tubulin inhibitors1. It can be used for the synthesis of 1, 2, 3, 4-tetrahydroisoquinoline-3-carboxylic acid (Tic), which has strong applications in peptides and peptidomimetics design and discovery2. 1, 2, 3, 4-tetrahydroisoquinoline has been made into some derivatives with potential for prevention of parkinsonism4, cancer treatment5 and acting as Anticonvulsant Agents6.
• Uses: 1,2,3,4-Tetrahydroisoquinoline is used as a reagent in the preparation of 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides as antiproliferative tubulin inhibitors.

Technology Process of 1,2,3,4-Tetrahydroisoquinoline

There total 121 articles about 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: 100.0%

N-acetyl-1,2,3,4-tetrahydroisoquinoline (14028-67-2) → 1,2,3,4-tetrahydroisoquinoline (91-21-4)

Guidance literature:

With ammonium bromide; ethylenediamine; at 70 ℃; for 5h; Reagent/catalyst; Temperature; Microwave irradiation;

Reference yield: 100.0%

1,2,3,4-tetrahydroisoquinolin-2-ol (54105-63-4) → 1,2,3,4-tetrahydroisoquinoline (91-21-4)

Guidance literature:

With indium; ammonium chloride; In ethanol; for 6h; Heating;

DOI:10.1021/ol034434l

Reference yield: 98.0%

isoquinoline (119-65-3) → 1,2,3,4-tetrahydroisoquinoline (91-21-4)

Guidance literature:

With hydrogen; In n-heptane; at 150 ℃; for 19h; under 22502.3 Torr; chemoselective reaction; Catalytic behavior; Sealed tube;

DOI:10.1021/acs.inorgchem.1c03098

upstream raw materials:

isoquinoline

1,4-dihydro-3(2H)-isoquinolinone

3,4-dihydro-isoquinoline 2-oxide

bis(2-chloromethyl)ether

Downstream raw materials:

2-(3,4-dihydro-1H-isoquinolin-2-yl)-ethanol

(4aS^*,8aS^*)-1,2,3,4,4a,5,6,7,8,8a-perhydroisoquinoline

2-cinnamyl-1,2,3,4-tetrahydroisoquinoline

3-bromo-4-(3,4-dihydro-1H-[2]isoquinolyl)-4-phenyl-butan-2-one

Refernces

• 1、 -. "CARBALDEHYDE OXIMES AS BUTYRYLCHOLINESTERASE REACTIVATORS". . . Retrieved 2022/02/07.
• 2、 Heizinger, Christian,Topf, Christoph,Vielhaber, Thomas. "Homogeneous pressure hydrogenation of quinolines effected by a bench-stable tungsten-based pre-catalyst". . p. 451 - 461. Retrieved 2021/11/11.