1-Chloro-6,7-dimethoxyisoquinoline

Base Information

• Chemical Name: 1-Chloro-6,7-dimethoxyisoquinoline
• CAS No.: 21560-29-2
• Molecular Formula: C11H10ClNO2
• Molecular Weight: 223.659
• Hs Code.: 2933499090
• European Community (EC) Number: 864-084-8
• DSSTox Substance ID: DTXSID80442904
• Wikidata: Q82260496
• Mol file: 21560-29-2.mol

Synonyms:1-Chloro-6,7-dimethoxyisoquinoline;21560-29-2;1-chloro-6,7-dimethoxy-isoquinoline;6,7-Dimethoxy-1-chloroisoquinoline;SCHEMBL5358941;DTXSID80442904;MPMDYPSDYGHVBM-UHFFFAOYSA-N;MFCD16249956;AKOS016012675;AS-61852;CS-0061919;EN300-181481;F50556;A879027

Chemical Property of 1-Chloro-6,7-dimethoxyisoquinoline

Chemical Property:

• Melting Point: 155-160 °C
• Boiling Point: 355.1±37.0 °C(Predicted)
• PKA: 2.92±0.40(Predicted)
• PSA: 31.35000
• Density: 1.265±0.06 g/cm3(Predicted)
• LogP: 2.90540
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 223.0400063
• Heavy Atom Count: 15
• Complexity: 215

Purity/Quality:

98.5% ^*data from raw suppliers

1-Chloro-6,7-dimethoxyisoquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C=CN=C2Cl)OC

Technology Process of 1-Chloro-6,7-dimethoxyisoquinoline

There total 12 articles about 1-Chloro-6,7-dimethoxyisoquinoline 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: 92.0%

6,7-dimethoxyisoquinoline-1(2H)-one (16101-63-6) → 1-chloro-6,7-dimethoxyisoquinoline (21560-29-2)

Guidance literature:

With trichlorophosphate; at 100 ℃; for 0.5h; Inert atmosphere; Microwave irradiation;

DOI:10.1002/anie.201610203

Reference yield: 34.0%

6,7-dimethoxyisoquinoline 2-oxide (40788-74-7) → 1-chloro-6,7-dimethoxyisoquinoline (21560-29-2)

Guidance literature:

With N,N-dimethyl-formamide; trichlorophosphate; In dichloromethane; at 40 ℃; for 6h; regioselective reaction; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2016.07.083

Reference yield:

6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one (493-49-2) → 1-chloro-6,7-dimethoxyisoquinoline (21560-29-2)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium/charcoal / 200 - 240 °C / Unter Stickstoff

2: phosphoryl chloride

With palladium on activated charcoal; trichlorophosphate;

upstream raw materials:

6,7-dimethoxy-isoquinolin-1-ol

6,7-dimethoxyisoquinoline

3,4-dimethoxycinnamic acid

3,4-dimethoxy-benzaldehyde

Downstream raw materials:

1-(4-fluorophenoxy)-6,7-dimethoxyisoquinoline

C₁₇H₁₃F₂NO₃

1-<2-(4-clorophenyl)ethyl>-6,7-dimethoxyisoquinoline

6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-isoquinoline

Refernces

• 1、 Wang, Dong,Wang, Yuxi,Zhao, Junjie,Li, Linna,Miao, Longfei,Wang, Dong,Sun, Hua,Yu, Peng. "A highly practical and convenient halogenation of fused heterocyclic N-oxides". . p. 5762 - 5768. Retrieved 2016/08/30.
• 2、 Hu, Yun-Jin,St.-Onge, Miguel,Laliberté, Sébastien,Vallée, Frédéric,Jin, Shujuan,Bedard, Leanne,Labrecque, Jean,Albert, Jeffrey S.. "Discovery of a 4-aryloxy-1H-pyrrolo[3,2-c]pyridine and a 1-aryloxyisoquinoline series of TRPA1 antagonists". supporting information. p. 3199 - 3203. Retrieved 2015/02/19.