1-Chloroisoquinoline

Base Information

• Chemical Name: 1-Chloroisoquinoline
• CAS No.: 19493-44-8
• Molecular Formula: C9H6ClN
• Molecular Weight: 163.606
• Hs Code.: 29334900
• Mol file: 19493-44-8.mol

Synonyms:NSC 170839;

Chemical Property of 1-Chloroisoquinoline

Chemical Property:

• Appearance/Colour: white to yellow low melting solid
• Vapor Pressure: 0.00902mmHg at 25°C
• Melting Point: 31-36 °C(lit.)
• Refractive Index: 1.652
• Boiling Point: 274.5 °C at 760 mmHg
• PKA: 2.03±0.30(Predicted)
• Flash Point: 158 °C
• PSA: 12.89000
• Density: 1.27 g/cm³
• LogP: 2.88820
• Storage Temp.: 0-10°C
• Water Solubility.: Insoluble in water.

Purity/Quality:

1-Chloroisoquinone ^*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:

• Uses: Used in a Mn-catalyzed cross-coupling with aryl- and alkylmagnesium halides.1 Also used in a Pd-catalyzed cross-coupling with heteroaryl boronic acids and esters.2 1-Chloroisoquinone is used in the preparation of new aminoisoquinolinylurea derivatives which show antiproliferative activity against melanoma cell lines. It can also be applied to the control of stor age and stability of unstable boronic acids. The product has been used in a Mn-catalyzed cross-coupling with aryl- and alkylmagnesium halides. It has also been used in a Pd-catalyzed cross-coupling with heteroaryl boronic acids and esters. Furthermore, it has been used in a homocoupling reaction to yield bis-isoquinoline, each enantiomer of which might be very useful as a chiral ligand for asymmetric synthesis. 1-Chloroisoquinone is used in the preparation of new aminoisoquinolinylurea derivatives which show antiproliferative activity against melanoma cell lines. It can also be applied to the control of storage age and stability of unstable boronic acids.

Technology Process of 1-Chloroisoquinoline

There total 16 articles about 1-Chloroisoquinoline 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%

1-hydroxyisoquinoline (491-30-5,87602-67-3) → 1-chloroisoquinoline (19493-44-8)

Guidance literature:

With trichlorophosphate; Heating;

DOI:10.1021/jm010330+

Reference yield: 92.0%

1-isoquinolinecarboxylic acid (486-73-7) → 1-chloroisoquinoline (19493-44-8)

Guidance literature:

With tert-butylhypochlorite; dichloromethane; sodium hydrogencarbonate; at 60 ℃; for 20h; Green chemistry;

DOI:10.1039/c9gc02407g

Reference yield: 87.5%

isoquinoline N-oxide (1532-72-5) → 1-chloroisoquinoline (19493-44-8)

Guidance literature:

With oxalyl dichloride; triethylamine; In dichloromethane; at -70 ℃; for 0.5h; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b01057

upstream raw materials:

isoquinoline N-oxide

isoquinolin-1-ylamine

N-methylisocarbostyril

2-Ethyl-1,2-dihydroisochinolin-1-on

Downstream raw materials:

4H-Benzoquinolizin-4-one

1-<2-(4'-Methoxyphenyl)-1,3-dithiane-2-yl>-isoquinoline

1-(2-Phenyl-1,3-dithiane-2-yl)-isoquinoline

1-methylisoquinoline

Refernces

• 1、 MO, JIANGWEN,PENG, YAN,WANG, YANYAN,WANG, ZHU,YAO, HAIPING. "Design, synthesis, and biological evaluation of isoquinolin-1(2H)-one derivates as tankyrase-1/2 inhibitors". . p. 132 - 137. Retrieved 2021/05/31.
• 2、 Fosu, Stacy C.,Hambira, Chido M.,Chen, Andrew D.,Fuchs, James R.,Nagib, David A.. "Site-Selective C–H Functionalization of (Hetero)Arenes via Transient, Non-symmetric Iodanes". supporting information. p. 417 - 428. Retrieved 2019/02/14.