953-14-0

Basic information

• Product Name: 1,2-Bis(4-chlorophenyl)hydrazine
• Synonyms: 1,2-Bis(4-chlorophenyl)hydrazine;4,4'-Dichlorohydrazobenzene;N,N'-Bis-(4-chloro-phenyl)-hydrazine
• CAS NO: 953-14-0
• Molecular Formula: C₁₂H₁₀Cl₂N₂
• Molecular Weight: 253.1272
• Mol File: 953-14-0.mol
• Article Data: 39

Chemical Properties

• Boiling Point: 288.6°Cat760mmHg
• Flash Point: 128.3°C
• Appearance: /
• Density: 1.405g/cm³
• Vapor Pressure: 0.00232mmHg at 25°C
• Refractive Index: 1.707
• CAS DataBase Reference: 1,2-Bis(4-chlorophenyl)hydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Bis(4-chlorophenyl)hydrazine(953-14-0)
• EPA Substance Registry System: 1,2-Bis(4-chlorophenyl)hydrazine(953-14-0)

Safety Data

• Hazardous Substances Data: 953-14-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 6721, 1996 DOI: 10.1016/S0040-4039(96)01451-7

InChI:InChI=1/C12H10Cl2N2/c13-9-1-5-11(6-2-9)15-16-12-7-3-10(14)4-8-12/h1-8,15-16H

Upstream product

• 614-26-6 4,4'-bis(chloro)azoxybenzene 
• 1602-00-2 bis-(4-chloro-phenyl)-diazene 
• 73183-34-3 bis(pinacol)diborane 
• 106-47-8 4-chloro-aniline 
• 100-00-5 4-chlorobenzonitrile 
• 30926-04-6 cis-4,4'-dichloroazobenzene 
• 21650-51-1 (E)-bis(4-chlorophenyl)diazene 

Downstream Products

• 412337-59-8 6-chloro-3-(4-chloro-anilino)-2-hydroxy-quinoline-4-carboxylic acid methyl ester 
• 855005-41-3 4-methyl-1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione 
• 165663-10-5 1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione 
• 30930-37-1 1-(4-chlorophenylamino)naphthalen-2-ol 
• 106-47-8 4-chloro-aniline 

Relevant articles and documents

Hydrogen peroxide based oxidation of hydrazines using HBr catalyst

Azo compounds (RN = NR′) are an important class of organic molecules that find wide application in organic synthesis. Herein, we report an efficient, practical and metal-free oxidation of hydrazines (RNH-NHR’) to azo compounds using 5 mol% HBr and hydrogen peroxide as terminal oxidant. This new method has been demonstrated by 40 examples with excellent yields. In addition, we showcased two examples of the one-pot sequential reactions involving our hydrazine oxidation/hydrolysis/Heck reaction or Cu-catalyzed N-arylation with aryl boronic acid. The distinct advantages of this protocol include metal-free catalysis, waste prevention, and easy operation.

Convenient semihydrogenation of azoarenes to hydrazoarenes using H2

The high atom-economical and eco-benign nature of hydrogenation reactions make them much more superior to conventional reduction and transfer hydrogenation. Herein, a convenient and highly selective hydrogenation reaction of azoarenes using molecular hydrogen to access diverse hydrazoarenes is reported. The present catalytic method is general and operationally simple, and it operates under exceedingly mild conditions (room temperature and 1 atm of hydrogen pressure). The reusability of catalysts used in this method is also successfully demonstrated.

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.