617-22-1

Basic information

• Product Name: 2,2-Dimethylhydrazobenzene
• Synonyms: 2,2-Dimethylhydrazobenzene;o-Hydrazotoluene
• CAS NO: 617-22-1
• Molecular Formula: C₁₄H₁₆N₂
• Molecular Weight: 213.29818
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 617-22-1.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 259°Cat760mmHg
• Flash Point: 105.3°C
• Appearance: /
• Density: 1.124g/cm³
• Vapor Pressure: 0.0133mmHg at 25°C
• Refractive Index: 1.664
• CAS DataBase Reference: 2,2-Dimethylhydrazobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethylhydrazobenzene(617-22-1)
• EPA Substance Registry System: 2,2-Dimethylhydrazobenzene(617-22-1)

Safety Data

• Hazardous Substances Data: 617-22-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 25, p. 1707, 1960 DOI: 10.1021/jo01080a005

InChI:InChI=1/C14H16N2/c1-11-7-3-5-9-13(11)15-16-14-10-6-4-8-12(14)2/h3-10,15-16H,1-2H3

Upstream product

• 584-90-7 trans-di-o-tolyl-diazene 
• 64-17-5 ethanol 
• 584-90-7 2,2'-dimethylazobenzene 
• 88-72-2 1-methyl-2-nitrobenzene 
• 7783-06-4 hydrogen sulfide 
• 7664-41-7 ammonia 
• 67-56-1 methanol 
• 71-43-2 benzene 
• 103-01-5 N-Phenylglycine 
• 956-31-0 N,N'-Di-o-tolyl-diazene N-oxide 
• 108-90-7 chlorobenzene 

Downstream Products

• 22695-18-7 N,N-di-o-tolylthiourea 
• 584-90-7 2,2'-dimethylazobenzene 
• 95-53-4 o-toluidine 
• 119-93-7 o-tolidin 
• 22264-22-8 3-(N,N'-Di-o-tolyl-hydrazinocarbonyl)-propionic acid methyl ester 
• 109689-54-5 3,3'-dimethyl-biphenyl-2,4'-diyldiamine 
• 866995-84-8 N-methyl-N,N'-di-o-tolyl-hydrazine 
• 584-90-7 trans-di-o-tolyl-diazene 
• 7583-27-9 4,4'-diiodo-3,3'-dimethylbiphenyl 
• 61794-96-5 4,4'-dibromo-3,3'-dimethyl-1,1'-biphenyl 
• 959163-35-0 N-diphenylphosphino-N,N'-di(o-tolyl)hydrazine 
• 22264-21-7 N,N'-Di-(o-tolyl)-3-carboxypropionhydrazid 
• 137182-63-9 4-acetyl-1,2-dihydro-5-methyl-1,2-bis(2-methylphenyl)-3H-pyrazol-3-one 
• 55908-51-5 1,2-dihydro-5-methyl-1,2-bis(2-methylphenyl)-3H-pyrazol-3-one 

Relevant articles and documents

Visible-Light-Promoted Diboron-Mediated Transfer Hydrogenation of Azobenzenes to Hydrazobenzenes

A visible-light-promoted transfer hydrogenation of azobenzenes has been developed. In the presence of B2pin2 and upon visible-light irradiation, the reactions proceeded smoothly in methanol at ambient temperature. The azobenzenes with diverse functional groups have been reduced to the corresponding hydrazobenzenes with a yield of up to 96%. Preliminary mechanistic studies indicated that the hydrogen atom comes from the solvent and the transformation is achieved through a radical pathway.

Visible-light-promoted decarboxylative addition cyclization of: N -aryl glycines and azobenzenes to access 1,2,4-triazolidines

Methods for the synthesis of 1,2,4-triazolidines are scarce. Herein, we report a visible-light-promoted decarboxylative addition cyclization of N-aryl glycines and azobenzenes to access such important compounds. Using commercially available methylene blue (MB) as an organic photocatalyst, the reaction proceeded smoothly in the absence of transition-metal catalysts at ambient temperature, affording the corresponding products, 1,2,4-triaryl 1,2,4-triazolidines, in good to excellent yields. This work demonstrates a new synthetic application of readily available azobenenes and provides a novel strategy for constructing 1,2,4-triazolidines.

Tandem selective reduction of nitroarenes catalyzed by palladium nanoclusters

We report a catalytic tandem reduction of nitroarenes by sodium borohydride (NaBH4) in aqueous solution under ambient conditions, which can selectively produce five categories of nitrogen-containing compounds: anilines, N-aryl hydroxylamines, azoxy-, azo- and hydrazo-compounds. The catalyst is in situ-generated ultrasmall palladium nanoclusters (Pd NCs, diameter of 1.3 ± 0.3 nm) from the reduction of Pd(OAc)2 by NaBH4. These highly active Pd NCs are stabilized by surface-coordinated nitroarenes, which inhibit the further growth and aggregation of Pd NCs. By controlling the concentration of Pd(OAc)2 (0.1-0.5 mol% of nitroarene) and NaBH4, the water/ethanol solvent ratio and the tandem reaction sequence, each of the five categories of N-containing compounds can be obtained with excellent yields (up to 98%) in less than 30 min at room temperature. This tunable catalytic tandem reaction works efficiently with a broad range of nitroarene substrates and offers a green and sustainable method for the rapid and large-scale production of valuable N-containing chemicals.