17721-96-9

Basic information

• Product Name: 2-nitroso-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 2-nitroso-1,2,3,4-tetrahydroisoquinoline;1,2,3,4-tetrahydro-2-nitroso-isoquinoline
• CAS NO: 17721-96-9
• Molecular Formula: C₉H₁₀N₂O
• Molecular Weight: 162.1885
• Mol File: 17721-96-9.mol
• Article Data: 17

Chemical Properties

• Melting Point: 48-50 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 341.2±31.0 °C(Predicted)
• Appearance: /
• Density: 1.21±0.1 g/cm3(Predicted)
• PKA: -4.66±0.20(Predicted)
• CAS DataBase Reference: 2-nitroso-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-nitroso-1,2,3,4-tetrahydroisoquinoline(17721-96-9)
• EPA Substance Registry System: 2-nitroso-1,2,3,4-tetrahydroisoquinoline(17721-96-9)

Safety Data

• Hazardous Substances Data: 17721-96-9(Hazardous Substances Data)

Usage

General Description

2-nitroso-1,2,3,4-tetrahydroisoquinoline is a chemical compound with the molecular formula C9H10N2O. It is a nitroso compound, which means it contains a nitroso group (-NO). This chemical is a derivative of tetrahydroisoquinoline, which is a group of compounds that contain a bicyclic structure with a nitrogen atom. 2-nitroso-1,2,3,4-tetrahydroisoquinoline has potential applications in medicinal chemistry, specifically in the synthesis of pharmaceuticals and as a building block for organic compounds. Additionally, it is important to handle this chemical with care, as nitroso compounds can be potentially hazardous if not used and stored properly.

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 155438-30-5 3,4-Dinitrofurazan 
• 14099-81-1 1,2,3,4-tetrahydroisoquinoline 
• 2744-08-3 decahydroisoquinoline 

Downstream Products

• 79492-44-7 2-benzylideneamino-1,2,3,4-tetrahydroisoquinoline 
• 19350-92-6 2-p-Toluenesulfonamido-1,2,3,4-tetrahydroisoquinoline 
• 79492-45-8 2-(p-nitrobenzylideneamino)-1,2,3,4-tetrahydroisoquinoline 
• 90872-67-6 N-methyl-3,4-dihydroisoquinolin-2(1H)-amine 
• 79492-26-5 2-amino-1,2,3,4-tetrahydro-isoquinoline-hydrochloride 
• 4836-98-0 1,2,3,4-tetrahydro-2-amino-isoquinoline 

Relevant articles and documents

Synthesis of secondary and tertiary aminofurazans

Reactions of nitrofurazans with primary and secondary amines were studied. Conditions were found which allow the efficient replacement of the nitro group with these nucleophiles. Transformations of the amidoxime fragment, which is bound to the furazan ring and contains an amino substituent, enable one to substantially expand the spectrum of polyfunctional derivatives. The structures of the amines synthesized were studied by X-ray diffraction analysis.

The Use of Potassium/Sodium Nitrite as a Nitrosating Agent in the Electrooxidative N-Nitrosation of Secondary Amines

We report herein on the electrochemical N-nitrosation of secondary amines using widely available sodium/potassium nitrite as a nitrosating agent. This approach not only eliminates the need for using a combination of sodium/potassium and a strong acid but also has good functional group tolerance. The reaction is compatible with the late-stage modification of pharmaceutical compounds and could be conducted in gram scale with a high reaction efficiency. Preliminary mechanistic studies indicate that the N-nitrosation occurs via the anodic oxidation of KNO2 into an NO2 radical which is then transformed into an NO+ cation.

Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation

ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.

Copper(II)-catalyzed oxidative N-nitrosation of secondary and tertiary amines with nitromethane under an oxygen atmosphere

The combination of a catalytic amount of Cu(OTf)2 and less than a stoichiometric amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under an O2 atmosphere effectively promoted the N-nitrosation of both secondary aromatic/aliphatic amines and tertiary aromatic amines with nitromethane (CH3NO2) leading to the preparation of N-nitrosamine derivatives.