209286-73-7

Basic information

• Product Name: 1-CHLORO-6-METHYLISOQUINOLINE
• Synonyms: 1-Chloro-6-methylisoquinoline; Isoquinoline, 1-chloro-6-methyl-
• CAS NO: 209286-73-7
• Molecular Formula: C₁₀H₈ClN
• Molecular Weight: 177.63
• EINECS: -0
• Mol File: 209286-73-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 304.946°C at 760 mmHg
• Flash Point: 166.858°C
• Appearance: /
• Density: 1.225g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 2.50±0.38(Predicted)
• CAS DataBase Reference: 1-CHLORO-6-METHYLISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CHLORO-6-METHYLISOQUINOLINE(209286-73-7)
• EPA Substance Registry System: 1-CHLORO-6-METHYLISOQUINOLINE(209286-73-7)

Safety Data

• Hazardous Substances Data: 209286-73-7(Hazardous Substances Data)

Usage

Description

1-Chloro-6-methylisoquinoline, with the CAS number 209286-73-7, is an organic compound belonging to the isoquinoline family. It is characterized by the presence of a chlorine atom at the 1st position and a methyl group at the 6th position in the isoquinoline ring. 1-CHLORO-6-METHYLISOQUINOLINE serves as a crucial intermediate in the synthesis of various biologically active molecules and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
1-Chloro-6-methylisoquinoline is used as a key intermediate in the synthesis of 5-membered aminoheterocyclic and 5,6or 6,6-membered bicyclic aminoheterocyclic inhibitors of ROCK (Rho-associated protein kinase). These inhibitors play a significant role in the treatment of heart failure by modulating the ROCK signaling pathway, which is involved in the regulation of cardiac function and remodeling.

InChI:InChI=1/C10H8ClN/c1-7-2-3-9-8(6-7)4-5-12-10(9)11/h2-6H,1H3

Upstream product

• 131002-10-3 6-methyl-isoquinolin-1-ol 
• 42398-73-2 6-methylisoquinoline 
• 70810-28-5 6-methylisoquinoline N-oxide 
• 131002-10-3 6-methyl-2H-isoquinolin-1-one 
• 108-95-2 phenol 

Downstream Products

• 234109-25-2 C₁₀H₇BrClN 
• 950516-24-2 C₁₀H₉ClN₂ 

Relevant articles and documents

Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN

A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.

Design, synthesis, and biological evaluation of pyrazinones containing novel P1 needles as inhibitors of TF/VIIa

Herein is described the design, synthesis, and enzymatic activity of a series of substituted pyrazinones as inhibitors of the TF/VIIa complex. These inhibitors were designed to explore replacement and variation of the P1 amidine described previously [J. Med. Chem. 2003, 46, 4050]. The P1 needle replacements were selected based upon their reduced basicity compared to the parent phenyl amidine (pKa ～ 12). A contributing factor towards the oral bioavailability of a compound is the ionization state of the compound in the intestinal tract. The desired outcome of the study was to identify an orally bioavailable TF-VIIa inhibitor.

Sulfonic acid sulfonylamino n-(heteroaralkyl)-azaheterocyclylamide compounds

The compounds of formula I herein exhibit useful pharmacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More specifically, they are inhibitors of the activity of Factor Xa. The present invention is directed to compounds of formula I, compositions containing compounds of formula I, and their use, for treating a patient suffering from, or subject to, a physiological condition which can be ameliorated by the administration of an inhibitor of the activity of Factor Xa.