161745-33-1

Basic information

• Product Name: (R)-2,6-diMethyl-1,2,3,4-tetrahydroquinoline
• Synonyms: (R)-2,6-diMethyl-1,2,3,4-tetrahydroquinoline;(2R)-1,2,3,4-Tetrahydro-2,6-dimethylquinoline
• CAS NO: 161745-33-1
• Molecular Formula: C₁₁H₁₅N
• Molecular Weight: 161.2435
• Mol File: 161745-33-1.mol

Chemical Properties

• Boiling Point: 271.324 °C at 760 mmHg
• Flash Point: 121.705 °C
• Appearance: /
• Density: 0.957 g/cm³
• CAS DataBase Reference: (R)-2,6-diMethyl-1,2,3,4-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2,6-diMethyl-1,2,3,4-tetrahydroquinoline(161745-33-1)
• EPA Substance Registry System: (R)-2,6-diMethyl-1,2,3,4-tetrahydroquinoline(161745-33-1)

Safety Data

• Hazardous Substances Data: 161745-33-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-2,6-diMethyl-1,2,3,4-tetrahydroquinoline serves as a key building block in the pharmaceutical industry, utilized for the synthesis of various medicinal compounds. Its unique structure allows for the development of drugs with specific therapeutic targets, contributing to the creation of novel treatments for a range of diseases.
Used in Agrochemical Production:
In the agrochemical sector, (R)-2,6-diMethyl-1,2,3,4-tetrahydroquinoline is employed as an intermediate in the synthesis of pesticides and other crop protection agents. Its incorporation aids in enhancing the effectiveness of these products, ensuring robust agricultural yields.
Used in Organic Synthesis:
As an intermediate in organic synthesis, (R)-2,6-diMethyl-1,2,3,4-tetrahydroquinoline is instrumental in the production of a wide array of chemical compounds. Its adaptability in chemical reactions facilitates the creation of new molecules with tailored properties for various applications.
Used in Biological and Pharmacological Research:
(R)-2,6-diMethyl-1,2,3,4-tetrahydroquinoline is also used in research settings to explore its potential as an antiviral and anticonvulsant agent. Studies on its biological activities are crucial for understanding its therapeutic potential and for developing new drugs based on its chemical structure.

Upstream product

• 16078-45-8 2,6-dimethyl-1,2,3,4-tetrahydroquinoline 
• 623-03-0 4-Cyanochlorobenzene 
• 98-56-6 4-chlorobenzotrifluoride 

Relevant articles and documents

Low-Temperature Nickel-Catalyzed C?N Cross-Coupling via Kinetic Resolution Enabled by a Bulky and Flexible Chiral N-Heterocyclic Carbene Ligand

The transition-metal-catalyzed C?N cross-coupling has revolutionized the construction of amines. Despite the innovations of multiple generations of ligands to modulate the reactivity of the metal center, ligands for the low-temperature enantioselective amination of aryl halides remain a coveted target of catalyst engineering. Designs that promote one elementary reaction often create bottlenecks at other steps. We here report an unprecedented low-temperature (as low as ?50 °C), enantioselective Ni-catalyzed C?N cross-coupling of aryl chlorides with sterically hindered secondary amines via a kinetic resolution process (s factor up to >300). A bulky yet flexible chiral N-heterocyclic carbene (NHC) ligand is leveraged to drive both oxidative addition and reductive elimination with low barriers and control the enantioselectivity. Computational studies indicate that the rotations of multiple σ-bonds on the C2-symmetric chiral ligand adapt to the changing needs of catalytic processes. We expect this design would be widely applicable to diverse transition states to achieve other challenging metal-catalyzed asymmetric cross-coupling reactions.

Deracemization of Phenyl-Substituted 2-Methyl-1,2,3,4-Tetrahydroquinolines by a Recombinant Monoamine Oxidase from Pseudomonas monteilii ZMU-T01

A monoamine oxidase (MAO5) from Pseudomonas monteilii ZMU-T01 was first heterologously expressed in Escherichia coli BL21(DE3) and then used as a biocatalyst for the deracemization of racemic 2-methyl-1,2,3,4-tetrahdroquinoline derivatives to yield the unreacted R enantiomer with up to >99 % ee. Sequence alignment revealed that MAO5 shared 14.7 % identity toward the well-studied monoamine oxidase (MAO-N).