6610-08-8

Basic information

• Product Name: 2-NITROSONAPHTHALENE
• Synonyms: 2-NITROSONAPHTHALENE
• CAS NO: 6610-08-8
• Molecular Formula: C₁₀H₇NO
• Molecular Weight: 157.18
• Mol File: 6610-08-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 281.82°C (rough estimate)
• Flash Point: 119.3°C
• Appearance: /
• Density: 1.1599 (rough estimate)
• Vapor Pressure: 0.00293mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• CAS DataBase Reference: 2-NITROSONAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITROSONAPHTHALENE(6610-08-8)
• EPA Substance Registry System: 2-NITROSONAPHTHALENE(6610-08-8)

Safety Data

• Hazardous Substances Data: 6610-08-8(Hazardous Substances Data)

Usage

Safety Profile

Questionable carcinogen withexperimental neoplastigenic and tumorigenic data.Mutation data reported. Many nitroso compounds arecarcinogens. When heated to decomposition it emits toxicfumes of NOx. See also NITROSO COMPOUNDS

InChI:InChI=1/C10H7NO/c12-11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H

Upstream product

• 32316-92-0 naphthalene-2-boronic acid 

Relevant articles and documents

DFT-Guided Phosphoric-Acid-Catalyzed Atroposelective Arene Functionalization of Nitrosonaphthalene

Guided by computational design, Tan and colleagues disclose a chiral phosphoric-acid-catalyzed asymmetric functionalization of naphthalenes with nitroso as the activating and directing group. This nucleophilic aromatic substitution reaction allows divergent access to two types of axially chiral arylindole frameworks with wide substrate generality under excellent enantiocontrol and, more importantly, offers a facile approach to the privileged NOBIN (2-amino-2′-hydroxy-1,1′-binaphthyl) structures. DFT calculations illustrate the plausible reaction pathway and provide additional insights into the origins of enantioselectivity.Functionalization of arenes represents the most efficient approach for constructing a core backbone of important aryl compounds. Compared with the well-developed electrophilic aromatic substitution and transition-metal-catalyzed C–H activation, nucleophilic aromatic substitution remains challenging because of the lack of a convenient route for rapid conversion of the σH adduct to other stable and versatile intermediates in situ. Guided by computational design, we were able to realize asymmetric nucleophilic aromatic substitution by introducing a nitroso group on naphthalene via chiral phosphoric acid catalysis. This strategy enables efficient construction of atropisomeric indole-naphthalenes and indole-anilines with excellent stereocontrol. Density functional theory (DFT) calculations provide further insights into the origins of enantioselectivity and the reaction mechanisms. The successful application in the synthesis of NOBINs (2-amino-2′-hydroxy-1,1′-binaphthyl) extends the utility of this strategy.Highly efficient conversion of inexpensive and readily available arene materials into high-value-added chiral molecules is of great importance in modern synthetic chemistry given the enormous potential of such structures in functional materials, pharmaceuticals, and other relevant chemical industries. Organocatalytic nucleophilic aromatic substitution enabled by an azo group offers an effective approach to enantioselective functionalization of naphthalene C–H bonds featuring an intramolecular oxidation of an unstabilized σH adduct. Premised on density functional theory (DFT) calculations, nitroso has emerged as another promising activating and oxidative group, whose synthetic potential is substantiated in the atroposelective synthesis of several groups of representative biaryl atropisomers processed by a chiral phosphoric acid catalyst. The success of this reaction explicitly exemplifies the ability of computational tools to streamline organic synthesis with intensified robustness in the disclosed strategy.

N-acetoxy-N-acetylaminoarenes and nitrosoarenes. One-electron non-enzymatic and enzymatic oxidation products of various carcinogenic aromatic acethydroxamic acids.

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