5822-13-9

Basic information

• Product Name: N-Benzyl-1,2-phenylenediamine
• Synonyms: N-Benzyl-1,2-phenylenediamine;N-Benzyl-2-aMino-aniline;N1-Benzylbenzene-1,2-diaMine;N-Benzyl-1,2-benzenediaMine;N1-Benzylphenylene-1,2-diamine, N1-(Phenylmethyl)benzene-1,2-diamine;2-(BenzylaMino)aniline;1,2-Benzenediamine, N1-(phenylmethyl)-;(2-aminophenyl)-(benzyl)amine
• CAS NO: 5822-13-9
• Molecular Formula: C₁₃H₁₄N₂
• Molecular Weight: 198.26366
• Mol File: 5822-13-9.mol
• Article Data: 56

Chemical Properties

• Melting Point: 163-165℃ (toluene )
• Boiling Point: 154 °C(Press: 0.1 Torr)
• Appearance: /
• Density: 1.153±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 5.48±0.10(Predicted)
• CAS DataBase Reference: N-Benzyl-1,2-phenylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyl-1,2-phenylenediamine(5822-13-9)
• EPA Substance Registry System: N-Benzyl-1,2-phenylenediamine(5822-13-9)

Safety Data

• Hazardous Substances Data: 5822-13-9(Hazardous Substances Data)

Usage

General Description

N-Benzyl-1,2-phenylenediamine is a chemical compound with the molecular formula C13H14N2. It is commonly used as an antioxidant and stabilizer in rubber and plastic products, as well as in hair dyes and other cosmetics. N-Benzyl-1,2-phenylenediamine also has applications in the production of dyes and pigments, and as an intermediate in organic synthesis. However,

InChI:InChI=1S/C13H14N2/c14-12-8-4-5-9-13(12)15-10-11-6-2-1-3-7-11/h1-9,15H,10,14H2

Upstream product

• 100-39-0 benzyl bromide 
• 95-54-5 1,2-diamino-benzene 
• 5729-06-6 N-benzyl-2-nitroaniline 
• 100-51-6 benzyl alcohol 
• 758640-21-0 N-Benzylaniline 
• 1493-27-2 ortho-nitrofluorobenzene 
• 100-46-9 benzylamine 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 88-73-3 2-Chloronitrobenzene 
• 88-74-4 2-nitro-aniline 
• 577-19-5 2-nitrophenyl bromide 
• 717-57-7 N-benzylidene-o-phenylenediamine 

Downstream Products

• 4981-92-4 1-benzylbenzimidazole 
• 65647-93-0 1-benzylquinoxaline-2,3(1H,4H)-dione 
• 28643-53-0 1,3-dihydro-1-(phenylmethyl)-2H-benzimidazol-2-one 
• 56463-14-0 N-benzyl-N′-methylbenzene-1,2-diamine 
• 1370557-67-7 N-benzyl-N'-pentylbenzene-1,2-diamine 
• 1370557-64-4 N-benzyl-N'-(4-methoxybenzyl)-benzene-1,2-diamine 
• 739-88-8 1-benzyl-2-phenyl-1H-1,3-benzimidazole 
• 23982-82-3 1-benzyl-2-(4-methylphenyl)-1H-benzimidazole 
• 23982-86-7 1-benzyl-2-(4-chlorophenyl)-1H-benzo[d]imidazole 
• 31493-51-3 1-benzyl-1,3-dihydro-2H-benzo-[d]-imidazole-2-thione 
• 949928-08-9 4-(2-phenyl-benzoimidazol-1-ylmethyl)-benzoic acid methyl ester 
• 1310486-83-9 methyl 4-(1-benzyl-1H-benzo[d]imidazole-2-yl)benzoate 
• 5805-83-4 1-benzyl-2-methylbenzimidazole 
• 1608149-23-0 C₁₃H₅⁽²⁾H₅N₂ 

Relevant articles and documents

Discovery of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as novel and potent bromodomain and extra-terminal (BET) inhibitors with anticancer efficacy

As epigenetic readers, bromodomain and extra-terminal domain (BET) family proteins bind to acetylated-lysine residues in histones and recruit protein complexes to promote transcription initiation and elongation. Inhibition of BET bromodomains by small molecule inhibitors has emerged as a promising therapeutic strategy for cancer. Herein, we describe our efforts toward the discovery of a novel series of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as BET inhibitors. Intensive structural modifications led to the identification of compound 35f as the most active inhibitor of BET BRD4 with selectivity against BET family proteins. Further biological studies revealed that compound 35f can arrest the cell cycle in G0/G1 phase and induce apoptosis via decreasing the expression of c-Myc and other proteins related to cell cycle and apoptosis. More importantly, compound 35f showed favorable pharmacokinetic properties and antitumor efficacy in MV4-11 mouse xenograft model with acceptable tolerability. These results indicated that BET inhibitors could be potentially used to treat hematologic malignancies and some solid tumors.

Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines

The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.

Synthesis, photochemical properties, and cytotoxicity of 10-alkylphenazin-2(10H)-ones

In the present study, the synthesis of a variety of 10-alkylphenazin-2(10H)-ones by oxidative coupling between N-alkylbenzene-1,2-diamine and 1,2,4-benzenetriol under an oxygen atmosphere was realized, and their photochemical and biological properties wer