52411-33-3

Basic information

• Product Name: 2,2'-(ethylenedithio)dianiline
• Synonyms: 2,2'-(ethylenedithio)dianiline;Cyanacure;2,2''-[1,2-Ethanediylbis-(thio)]-bis-(benzenamine);2,2'-(Ethylenebisthio)bisaniline;2,2'-(Ethylenebisthio)dianiline;Ethylenebis(2-aminophenyl sulfide);2,2'-(Ethylenedithio)bis(aniline);2,2-(ETHANE-1,2-DIYLBIS(SULFANEDIYL))DIANILINE
• CAS NO: 52411-33-3
• Molecular Formula: C₁₄H₁₆N₂S₂
• Molecular Weight: 276.42024
• EINECS: 257-901-9
• Product Categories: Amines;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 52411-33-3.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 452.5 °C at 760 mmHg
• Flash Point: 227.5 °C
• Appearance: /
• Density: 1.2368 (rough estimate)
• Refractive Index: 1.5700 (estimate)
• CAS DataBase Reference: 2,2'-(ethylenedithio)dianiline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-(ethylenedithio)dianiline(52411-33-3)
• EPA Substance Registry System: 2,2'-(ethylenedithio)dianiline(52411-33-3)

Safety Data

• Hazardous Substances Data: 52411-33-3(Hazardous Substances Data)

Usage

General Description

2,2'-(ethylenedithio)dianiline is a chemical compound with the molecular formula C10H12N2S2. It is a yellow to brown solid that is primarily used in the production of rubber products as a vulcanization accelerator. It is also used as an intermediate in the production of dyes, pigments, and other chemical compounds. This chemical is considered to be toxic if ingested, inhaled, or absorbed through the skin, and it may cause skin and eye irritation. It is important to handle and store 2,2'-(ethylenedithio)dianiline with care and in accordance with safety regulations.

Upstream product

• 71532-96-2 1,2-di(o-nitrophenolthio)ethane 
• 106-93-4 ethylene dibromide 
• 137-07-5 2-amino-benzenethiol 
• 107-06-2 1,2-dichloro-ethane 
• 4875-10-9 o-nitrothiophenol 
• 624-73-7 1,2-Diiodoethane 
• 95-16-9 1,3-Benzothiazole 

Downstream Products

• 861522-93-2 1,4-bis((2-acetylamidophenyl)thio)ethane 
• 117585-67-8 1,2-di-(o-salicylaldiminophenylthio)ethane 
• 21620-34-8 1,10-diaza-5,6,15,17-tetrathia-2,3:8,9:12,13,18:19-tetrabenzocyclododeca-10,20-diene 
• 140161-65-5 1,2-Bisethane 
• 126292-73-7 15,16-dihydro-7-phenyl-5H-dibenzo-1,11,4,5,7,8-dithiatetraazacyclotridecyne 
• 140161-69-9 C₂₆H₂₀Cl₂N₄O₂S₂ 
• 188492-09-3 1,2-bis(2-(4-methylbenzylideneamino)phenylthio)ethane 
• 188492-11-7 N,N'-bis-(4-chlorobenzylidene)-1,2-bis(2-aminophenylthio)ethane 
• 188492-12-8 1,2-bis(2-(4-nitrobenzylideneamino)phenylthio)ethane 
• 188492-08-2 1,2-bis(2-(benzylideneamino)phenylthio)ethane 
• 188492-10-6 1,2-bis(2-(4-methoxybenzylideneamino)phenylthio)ethane 
• 327040-85-7 1,2-bis[O-(bromoacetamido)phenylthio]ethane 
• 5325-20-2 2H-1,4-benzothiazin-3-one 
• 557-24-4 maleamic acid 

Relevant articles and documents

Azo-azomethine dyes with N, O, S donor set of atoms and their Ni(II) complexes: Synthesis, characterization and spectral properties

New azo-azomethine dyes, L1-L3, with N 2S2O2 donor set of atoms have been synthesized via condensation reaction of 1,2-bis(2-aminophenylthio)ethane with 5-(4-X-phenyl)-azo-salicylaldehyde (X = Cl, OMe and Me). The new dyes were characterized by IR, UV-Vis, 1H NMR and fluorescence spectroscopy as well as mass spectrometry and elemental analysis. Mononuclear nickel(II) complexes of the dyes have been also prepared. The crystal structure of [NiL1]·0.5H2O was determined by single-crystal X-ray diffraction. The thermal analysis data indicate that all prepared dyes, L1-L3, are thermally stable up to 320 C. The fluorescence behavior of the prepared complexes have been also investigated and compared to those of L1-L3.

Development of a scaleable synthesis for 1,2-bis(2-aminophenylthio)ethane (APO-Link) used in the production of bismaleimide resin

The diamine reagent 1,2-bis(2-aminophenylthio)ethane is no longer commercially available but is still required for the synthesis of the bismaleimide resin, APO-BMI, used in syntactic foams. In this work, we examined the hydrolysis of benzothiazole followed by reaction with dichloroethane or dibromoethane. The deprotonation of 2-aminothiophenoI followed by reaction with dibromoethane was also investigated and later optimized for scale-up by scrutinizing all aspects of the reaction conditions, work-up, and recrystallization. On bench-scale, the optimized procedure consistently produced a 75-80% overall yield of finely divided, high purity product (>95%). The material was also produced on both a 100 Ib scale and a 200 Ib scale using the optimized process, giving high quality material in excellent yield.

Synthesis and characterization of a thioether Schiff base ligand and its metal complexes and crystal structure determination of the nickel(II) complex

Reactions of 1,2-di(o-aminophenylthio)ethane with 3-ethoxy-2-hydroxybenzaldehyde yield the new hexadentate N2S2O2 donor thioether Schiff base 1,2-bis(2-((2-(thio)phenylimino)methyl)-6-ethoxyphenol)ethane (H2L). Ni(II), Zn(II), Cd(II), and Hg(II) complexes of this ligand were prepared. Of these complexes, [NiL]·2H2O has been structurally characterized by X-ray crystallography. The coordination geometry around Ni(II) was described as octahedral. Zn(II), Cd(II), and Hg(II) complexes and the Schiff base ligand have been characterized by CHN analyses, molar conductivity, UV-vis, FT-IR, 1H, and 13C NMR spectroscopy.

Photocatalytic and electrocatalytic hydrogen production using nickel complexes supported by hemilabile and non-innocent ligands

Nickel complexes with non-innocent ligands generated by one-electron reduction of octahedral Schiff base nickel(ii) complexes with hemilabile ligands exhibited excellent catalytic activities of over 5000 TONs through a metal-ligand cooperation mechanism for hydrogen evolution from water under visible light irradiation.

Bis(2-cyanoacetamides): Versatile precursors for bis(dihydropyridine-3,5-dicarbonitriles)

Bis(6-amino-1,2-dihydropyridine-3,5-dicarbonitriles) containing thioether linkages are prepared via the condensation of bis(cyanoacetamides) with α-substituted cinnamonitriles in the presence of piperidine. The target compounds can also be obtained via a three-component reaction of bis(cyanoacetamides) with two equivalents of both aldehydes and malononitrile in ethanol containing piperidine as a base.