60518-41-4

Basic information

• Product Name: 7-chloro-3,4-dihydroisoquinoline
• Synonyms: 7-chloro-3,4-dihydroisoquinoline
• CAS NO: 60518-41-4
• Molecular Formula: C₉H₈ClN
• Molecular Weight: 165.61952
• Mol File: 60518-41-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 277.0±40.0 °C(Predicted)
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.54±0.20(Predicted)
• CAS DataBase Reference: 7-chloro-3,4-dihydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 7-chloro-3,4-dihydroisoquinoline(60518-41-4)
• EPA Substance Registry System: 7-chloro-3,4-dihydroisoquinoline(60518-41-4)

Safety Data

• Hazardous Substances Data: 60518-41-4(Hazardous Substances Data)

Usage

General Description

7-chloro-3,4-dihydroisoquinoline is an organic compound that belongs to the class of isoquinolines. It is a chlorinated derivative of 3,4-dihydroisoquinoline and is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. The presence of the chloro group on the isoquinoline ring imparts certain chemical and biological properties to the compound, making it useful in the development of various medicinal and agricultural products. Additionally, it is also used as a building block in the synthesis of complex organic molecules, making it a valuable compound in the field of organic chemistry.

Upstream product

• 73075-45-3 7-chloro-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 82771-60-6 7-chloro-1,2,3,4-tetrahydro-isoquinoline 

Downstream Products

• 1346176-91-7 C₁₇H₁₃ClN₂O₂ 
• 1346177-11-4 C₂₅H₂₁ClN₂O₄S 

Relevant articles and documents

Aza-Nazarov Cyclization Reactions via Anion Exchange Catalysis

A catalytic aza-Nazarov cyclization between 3,4-dihydroisoquinolines and α,β-unsaturated acyl chlorides has been developed to access α-methylene-?-lactam products in good yields (up to 79%) as single diastereomers. The reactions proceed efficiently when AgOTf is used as an anion exchange catalyst with a 20 mol % loading at 80 °C. Computational studies were performed to investigate the reaction mechanism, and the findings support the role of the ?TMS group in reducing the reaction barrier of the key cyclization step.

Discovery of TAK-981, a First-in-Class Inhibitor of SUMO-Activating Enzyme for the Treatment of Cancer

SUMOylation is a reversible post-translational modification that regulates protein function through covalent attachment of small ubiquitin-like modifier (SUMO) proteins. The process of SUMOylating proteins involves an enzymatic cascade, the first step of which entails the activation of a SUMO protein through an ATP-dependent process catalyzed by SUMO-activating enzyme (SAE). Here, we describe the identification of TAK-981, a mechanism-based inhibitor of SAE which forms a SUMO-TAK-981 adduct as the inhibitory species within the enzyme catalytic site. Optimization of selectivity against related enzymes as well as enhancement of mean residence time of the adduct were critical to the identification of compounds with potent cellular pathway inhibition and ultimately a prolonged pharmacodynamic effect and efficacy in preclinical tumor models, culminating in the identification of the clinical molecule TAK-981.

Aza-Nazarov Cyclization Reactions via Anion Exchange Catalysis

A catalytic aza-Nazarov cyclization between 3,4-dihydroisoquinolines and α,β-unsaturated acyl chlorides has been developed to access α-methylene-γ-lactam products in good yields (up to 79%) as single diastereomers. The reactions proceed efficiently when AgOTf is used as an anion exchange catalyst with a 20 mol % loading at 80 °C. Computational studies were performed to investigate the reaction mechanism, and the findings support the role of the -TMS group in reducing the reaction barrier of the key cyclization step.