612-98-6

Basic information

• Product Name: Nitrosobenzylphenylamine
• Synonyms: Benzylphenylnitrosamine;Benzylphenylnitrosoamine;N-Benzyl-N-nitrosoaniline;Nitrosobenzylphenylamine;N-Nitroso-N-benzylaniline;N-Phenyl-N-nitrosobenzenemethanamine
• CAS NO: 612-98-6
• Molecular Formula: C₁₃H₁₂N₂O
• Molecular Weight: 212.27
• Mol File: 612-98-6.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 352.09°C (rough estimate)
• Flash Point: 186°C
• Appearance: /
• Density: 1.1128 (rough estimate)
• Vapor Pressure: 4.26E-06mmHg at 25°C
• Refractive Index: 1.6920 (estimate)
• CAS DataBase Reference: Nitrosobenzylphenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Nitrosobenzylphenylamine(612-98-6)
• EPA Substance Registry System: Nitrosobenzylphenylamine(612-98-6)

Safety Data

• Hazardous Substances Data: 612-98-6(Hazardous Substances Data)

Usage

Safety Profile

Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx. Seealso NITROSAMINES and N-NITROSOCOMPOUNDS.

Purification Methods

Crystallise the amine from absolute EtOH (yellow needles) and dry it in air. It is slightly soluble in organic solvents. [Beilstein 12 H 1071, 12 II 335, 12 III 2335.]

InChI:InChI=1/C13H12N2O/c16-14-15(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h1-10H,11H2

Upstream product

• 91-73-6 N,N-dibenzylaniline 
• 509-14-8 tetranitromethane 
• 758640-21-0 N-Benzylaniline 
• 110-46-3 isopentyl nitrite 
• 56-23-5 tetrachloromethane 
• 40756-81-8 1,4-dibenzyl-1,4-diphenyl-tetraz-2-ene 

Downstream Products

• 758640-21-0 N-Benzylaniline 
• 38210-45-6 2-(benzo[b]thiophen-2-yl)benzenamine 
• 739-88-8 1-benzyl-2-phenyl-1H-1,3-benzimidazole 
• 152907-85-2 (2-benzylamino-phenyl)-(phenyl)-methanone 
• 3469-20-3 2,3-diphenyl-1H-indole 
• 117788-15-5 1-benzyl-2,3-diphenyl-1H-indole 
• 1135-34-8 benzyliden-aniline; bis hydrochloride of benzylidenaniline 
• 5729-06-6 N-benzyl-2-nitroaniline 
• 14309-92-3 N-benzyl-4-nitroaniline 
• 538-51-2 benzylidene phenylamine 
• 85046-51-1 N-nitroso N-benzyl-N-(4-nitroaniline) 
• 79909-42-5 3-Benzyl-2-(4-methoxy-phenyl)-3H-benzo[1,3,2]thiazaphosphole 2-sulfide 

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.

Rhodium-catalyzed tandem acylmethylation/annulation ofN-nitrosoanilines with sulfoxonium ylides for the synthesis of substituted indazoleN-oxides

An atom-economical protocol for synthesizing indazoleN-oxides from readily availableN-nitrosoanilines and sulfoxonium ylides through the rhodium(iii)-catalyzed C-H activation and cyclization reaction is described here. This protocol employs nitroso as a traceless directing group. The transformation features powerful reactivity, tolerates various functional groups, and proceeds with moderate to good yields under an ambient atmosphere, providing a straightforward approach to access structurally diverse and valuable indazoleN-oxide derivatives. Importantly, this new annulation process represents a hitherto unobserved reactivity pattern for theN-nitroso group.

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.