5825-44-5

Basic information

• Product Name: Quinoline, 1,2,3,4-tetrahydro-1-nitroso-
• Synonyms: 1-nitroso-1,2,3,4-tetrahydroquinoline;Tetrahydro-N-nitrosochinolin;Quinoline,1,2,3,4-tetrahydro-1-nitroso;N-nitroso-1,2,3,4-tetrahydroquinoline;N-Nitroso-tetrahydrochinolin;1-Nitroso-1,2,3,4-tetrahydro-chinolin;1,2,3,4-tetrahydro-1-nitrosoquinoline
• CAS NO: 5825-44-5
• Molecular Formula: C9H10N2O
• Molecular Weight: 162.191
• Mol File: 5825-44-5.mol
• Article Data: 32

Chemical Properties

• CAS DataBase Reference: Quinoline, 1,2,3,4-tetrahydro-1-nitroso-(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline, 1,2,3,4-tetrahydro-1-nitroso-(5825-44-5)
• EPA Substance Registry System: Quinoline, 1,2,3,4-tetrahydro-1-nitroso-(5825-44-5)

Safety Data

• Hazardous Substances Data: 5825-44-5(Hazardous Substances Data)

Upstream product

• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 110-46-3 isopentyl nitrite 
• 2739-17-5 1,2,3,4-tetrahydroquinoline hydrochloride 
• 767-92-0 decahydroquinoline 

Downstream Products

• 5825-45-6 1-amino-1,2,3,4-tetrahydroquinoline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 767-92-0 decahydroquinoline 
• 303801-64-1 3,4-dihydro-2H-quinolin-1-ylamine hydrochloride 
• 313670-69-8 4-((7aR,11aS)-5,6,8,9,11,11a-hexahydro-4H,7aH-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-yl)-1-(4-fluorophenyl)-1-butanone 
• 313670-67-6 4-((7aS,11aR)-5,6,8,9,11,11a-hexahydro-4H,7aH-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-yl)-1-(4-fluorophenyl)-1-butanone 

Relevant articles and documents

One-Pot Tandem ortho-Naphthoquinone-Catalyzed Aerobic Nitrosation of N-Alkylanilines and Rh(III)-Catalyzed C-H Functionalization Sequence to Indole and Aniline Derivatives

The nitroso group served as a traceless directing group for the C-H functionalization of N-alkylanilines, ultimately removed after functioning either as an internal oxidant or under subsequent reducing conditions. The unique ability of o-NQ catalysts to aerobically oxidize the N-alkylanilines without using solvents and stoichiometric amounts of oxidants has rendered the new opportunity to develop the telescoped catalyst systems without a need for directly handling the hazardous N-nitroso compounds.

Access to Branched Allylarenes via Rhodium(III)-Catalyzed C-H Allylation of (Hetero)arenes with 2-Methylidenetrimethylene Carbonate

A rhodium(III)-catalyzed C-H allylation of (hetero)arenes by using 2-methylidenetrimethylene carbonate as an efficient allylic source has been developed for the first time. Five different directing groups including oxime, N-nitroso, purine, pyridine, and pyrimidine were compatible, delivering various branched allylarenes bearing an allylic hydroxyl group in moderate to excellent yields.

Rhodium(iii)-catalyzed indole synthesis at room temperature using the transient oxidizing directing group strategy

Rh-catalyzed reactions of N-alkyl anilines with internal alkynes at room temperature have been developed using an in situ generated N-nitroso group as a transient oxidizing directing group. Due to mild reaction conditions, this method enabled synthesis of a broad range of N-alkyl indoles, including even two indole-based medicinal compounds. Our work disclosed the feasibility of the transient oxidizing directing group strategy in C-H functionalization reactions, which possesses the potential to enhance overall step-economy and impart new reactivity patterns to substrates.