6-Chloro-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: 6-Chloro-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 33537-99-4
• Molecular Formula: C9H10ClN
• Molecular Weight: 167.638
• Hs Code.: 2933499090
• European Community (EC) Number: 821-410-3
• ChEMBL ID: CHEMBL344495
• DSSTox Substance ID: DTXSID90472772
• Wikidata: Q72459609
• Mol file: 33537-99-4.mol

Synonyms:6-chloro-1,2,3,4-tetrahydroisoquinoline;33537-99-4;6-Chloro-1,2,3,4-tetrahydro-isoquinoline;ISOQUINOLINE, 6-CHLORO-1,2,3,4-TETRAHYDRO-;MFCD06739156;SCHEMBL532012;CHEMBL344495;DTXSID90472772;NSURINBXOVVUNR-UHFFFAOYSA-N;BCP26776;AKOS006229308;AB28730;CS-W005061;DS-11102;SY041607;A5971;AM20040201;FT-0696810;EN300-119682;J-019243;6-Chloro-1,2,3,4-tetrahydroisoquinoline, AldrichCPR;F9995-1251

Chemical Property of 6-Chloro-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

• Vapor Pressure: 0.008mmHg at 25°C
• Melting Point: 189-191 °C(Solv: ethanol (64-17-5))
• Refractive Index: 1.56
• Boiling Point: 267.686 °C at 760 mmHg
• PKA: 9.25±0.20(Predicted)
• Flash Point: 115.693 °C
• PSA: 12.03000
• Density: 1.162 g/cm³
• LogP: 2.31450
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 167.0501770
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

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

6-Chloro-1,2,3,4-tetrahydroisoquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCC2=C1C=C(C=C2)Cl
• Uses: 6-Chloro-1,2,3,4-tetrahydroisoquinoline

Technology Process of 6-Chloro-1,2,3,4-tetrahydroisoquinoline

There total 22 articles about 6-Chloro-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: 45.0%

N,N-bis(p-chlorobenzylamino)ethane dihydrobromide → 6‐chloro‐1,2,3,4‐tetrahydroisoquinoline (33537-99-4) + 4-chlorobenzylamine (104-86-9)

Guidance literature:

With aluminium trichloride; In decalin; at 180 ℃; for 2h;

DOI:10.1080/00397919708004118

Reference yield:

6-chloro-3,4-dihydro-1(2H)-isoquinolinone (22246-02-2) → 6‐chloro‐1,2,3,4‐tetrahydroisoquinoline (33537-99-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 12h; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.9b00191

Reference yield:

phenol (108-95-2,27073-41-2) → 6‐chloro‐1,2,3,4‐tetrahydroisoquinoline (33537-99-4)

Guidance literature:

With hydrogen bromide; In acetic acid;

upstream raw materials:

6-chloroisoquinoline

N-(2-methoxycarbonylethylsulfonyl)-6-chloro-1,2,3,4-tetrahydroisoquinoline

1-Chloro-3-((Z)-2-nitro-vinyl)-benzene

N-<2-(3-chlorophenyl)ethyl>acetamide

Downstream raw materials:

6-chloro-2-(2-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline

Refernces

• 1、 Lu, Cong,Su, Zhishan,Jing, Dong,Jin, Songyang,Xie, Lijuan,Li, Liangrui,Zheng, Ke. "Intramolecular Reductive Cyclization of o-Nitroarenes via Biradical Recombination". . p. 1438 - 1443. Retrieved 2019/03/07.
• 2、 Li, Jian,Wang, Zheng-Bing,Xu, Yue,Lu, Xue-Chen,Zhu, Shang-Rong,Liu, Li. "Catalyst-free cyclization of anthranils and cyclic amines: One-step synthesis of rutaecarpine". . p. 12072 - 12075. Retrieved 2019/10/14.