72995-16-5

Basic information

• Product Name: 5-Chloro-1,2,3,4-tetrahydroquinoline
• Synonyms: 5-Chloro-1,2,3,4-tetrahydroquinoline
• CAS NO: 72995-16-5
• Molecular Formula: C9H10ClN
• Molecular Weight: 167.6354
• Mol File: 72995-16-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 281.9±29.0 °C(Predicted)
• Appearance: /
• Density: 1.162±0.06 g/cm3(Predicted)
• PKA: 4.23±0.20(Predicted)
• CAS DataBase Reference: 5-Chloro-1,2,3,4-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-1,2,3,4-tetrahydroquinoline(72995-16-5)
• EPA Substance Registry System: 5-Chloro-1,2,3,4-tetrahydroquinoline(72995-16-5)

Safety Data

• Hazardous Substances Data: 72995-16-5(Hazardous Substances Data)

Upstream product

• 73045-32-6 4-chloro-1-indanone oxime 
• 611-34-7 5-Aminoquinoline 
• 635-27-8 5-chloroquinoline 
• 126401-55-6 5amino-3,4-dihydro-2(1H)-quinolinone hydrochloride 
• 72995-15-4 5-chloro-3,4-dihydro-2(1H)-quinolinone 

Relevant articles and documents

Homogeneous pressure hydrogenation of quinolines effected by a bench-stable tungsten-based pre-catalyst

We report on an operationally simple catalytic method for the tungsten-catalyzed hydrogenation of quinolines through the use of the easily handled and self-contained precursor [WCl(η5-Cp)(CO)3]. This half sandwich complex is indefinitely storable on the bench in simple screw-capped bottles or stoppered flasks and can, if required, be prepared on a multi-gram scale while the actual catalytic transformations were performed in the presence of a Lewis acid in order to achieve both decent substrate conversions and product yields. The described method represents a facile and atom-efficient access to a variety of 1,2,3,4-tetrahydroquinolines that circumvents the use of cost-intensive and oxygen-sensitive phosphine ligands as well as auxiliary hydride reagents.

Synthesis of N-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C-H Amination

We report both an intermolecular C-H amination of arenes to access N-methylanilines and an intramolecular variant for the synthesis of tetrahydroquinolines. A newly developed, highly electrophilic aminating reagent was key for the direct synthesis of unprotected N-methylanilines from simple arenes. The reactions display a broad functional group tolerance and employ catalytic amounts of a benign iron salt under mild reaction conditions.

Liberating N-CNTs Confined Highly Dispersed Co?Nx Sites for Selective Hydrogenation of Quinolines

Selective hydrogenation of quinoline and its derivatives is an important means to produce corresponding 1,2,3,4-tetrahydroquinolines for a wide spectrum of applications. A facile and efficient “laser irradiation in liquid” technique to liberate the inaccessible highly dispersed Co?Nx active sites confined inside N-doped carbon nanotubes is demonstrated. The liberated Co?Nx sites possess generic catalytic activities toward selective hydrogenation of quinoline and its hydroxyl, methyl, and halogen substituted derivatives into corresponding 1,2,3,4-tetrahydroquinolines with almost 100% conversion efficiency and selectivity. This laser irradiation treatment approach should be widely applicable to unlock the catalytic powers of inaccessible catalytic active sites confined by other materials.