621-95-4

Basic information

• Product Name: 4,4'-Ethylenedianiline
• Synonyms: 4,4'-diaminodibenzyl;4,4′-Ethylendianilin;α,αμ-Bi-p-toluidine, 4,4μ-Diaminobibenzyl;TIMTEC-BB SBB008520;1,2-Bis(4-Aminophenyl)ethane;1,2-Bis(p-aminophenyl)ethane;4,4’-(1,2-ethanediyl)bis-benzenamin;4,4’-ethylenebis(aniline)
• CAS NO: 621-95-4
• Molecular Formula: C₁₄H₁₆N₂
• Molecular Weight: 212.29
• EINECS: 210-716-7
• Mol File: 621-95-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 133-137 °C(lit.)
• Boiling Point: 342.14°C (rough estimate)
• Flash Point: 220.6 °C
• Appearance: Beige powder
• Density: 0.9678 (rough estimate)
• Vapor Pressure: 0.001Pa at 20℃
• Refractive Index: 1.4400 (estimate)
• Storage Temp.: room temp
• PKA: 5.17±0.10(Predicted)
• BRN: 394999
• CAS DataBase Reference: 4,4'-Ethylenedianiline(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Ethylenedianiline(621-95-4)
• EPA Substance Registry System: 4,4'-Ethylenedianiline(621-95-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36/37
• WGK Germany: 2
• RTECS: BY0200000
• HazardClass: IRRITANT
• Hazardous Substances Data: 621-95-4(Hazardous Substances Data)

Usage

Description

4,4'-Ethylenedianiline, also known as 4,4'-Diaminodiphenyl ether, is an organic compound with the chemical formula C14H14N2. It is a white crystalline solid that is soluble in organic solvents and has a molecular weight of 218.28 g/mol. 4,4'-Ethylenedianiline is known for its chemical reactivity and is commonly used as a reagent in various chemical synthesis processes.

Uses

Used in Chemical Synthesis:
4,4'-Ethylenedianiline is used as a reagent in the synthesis of new substituted Bis[2-Imino-3(substituted)-4-phenyl-3H-thiazole] derivatives. These derivatives exhibit potential antibacterial activity, making them valuable for the development of new antimicrobial agents.
Used in Analytical Chemistry:
4,4'-Ethylenedianiline may be used as an internal standard for the determination of 4,4'-methylenedianiline in urine samples using gas chromatography coupled with mass spectrometry (GC-MS). This application is crucial for monitoring occupational exposure to 4,4'-methylenedianiline, which is a potential carcinogen and a high-production-volume chemical used in the manufacturing of polyurethane foams and other industrial products.

Upstream product

• 736-30-1 1,2-bis(4-nitrophenyl)ethane 
• 64-17-5 ethanol 
• 106-49-0 p-toluidine 
• 7803-57-8 hydrazine hydrate 
• 111-46-6 diethylene glycol 
• 736-31-2 trans-4,4'-dinitrostilbene 
• 104-03-0 4-nitrobenzeneacetic acid 
• 100-14-1 4-nitrobenzyl chloride 
• 99-99-0 1-methyl-4-nitrobenzene 
• 619-93-2 4,4'-dinitro stilbene 
• 2609-49-6 diethyl p-nitrobenzylphosphonate 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 2922-41-0 (p-aminophenyl)alanine 
• 621-96-5 4,4'-diaminostilbene 

Downstream Products

• 411221-08-4 N,N'-bibenzyl-4,4'-diyl-bis-benzenesulfonamide 
• 6052-84-2 4,4'-ethylenediphenol 
• 13190-56-2 4,4'-ethanediyl-bis-cyclohexylamine 
• 56934-69-1 N-(4-{2-[4-(Ethoxyoxalyl-amino)-phenyl]-ethyl}-phenyl)-oxalamic acid ethyl ester 
• 116282-03-2 C₄₆H₅₄N₆O₄P₂S₂ 
• 71520-29-1 N,N'-bis(p-methylbenzylidene)-α,α'-bi-p-toluidine 
• 75472-33-2 N,N-bis(p-methoxyphenylbenzylidene)-α,α'-bi-p-toluidine 
• 96615-76-8 1,1'-(1,2-ethanediyldi-4,1-phenylene)bis<1,6-dihydro-6-phenyl-1,3,5-triazine-2,4-diamine> dihydrochloride 
• 4231-43-0 N,N'-disalicylidene-4,4'-diaminobibenzyl 
• 96615-74-6 C₁₈H₂₄N₁₀*2ClH 
• 93250-38-5 C₂₆H₂₂N₄O₄ 
• 71520-25-7 N,N'-bis(4-pentoxybenzylidene)-4,4'-ethylenedi(phenylamine) 

Relevant articles and documents

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The electrochemical behavior of titanium oxysulfate, used as a redox mediator in the reduction of 4, 4'-dinitrodiben-zyl, is studied in a 5 N H 2S04/EtOH 50: 50 medium. The role played by electrogenerated Ti3+ ions in the chemical reduction of nitro groups is also defined. The results obtained allow the determination of the most suitable conditions leading to selective syntheses. Macroscale electrolyses at a constant potential in the presence of TiOS04 give 4, 4'-diaminodi-benzyl with a great purity and a higher yield (93%) than without mediator (75%). The homogeneous chemical reduction of 4, 4'-dinitrodibenzyl by first electrogenerating the Ti3+ ions, then adding the organic substrate, is particularly selective. The nature of the reduction products depends on the [Ti3+]/[dinitro derivative] ratio. The 4-amino-4'-nitrodiben-zyl is synthesized in a 70% yield for a 6: 1 ratio whereas the amount of diamino derivative increases and can constitute the sole reduction product for higher ratios. A comparison is made with 1, 5-and 1, 8-dinitronaphthalenes and 2, 2'-di-nitrodiphenyl. Using a 6: 1 ratio, l-amino-8-nitronaphthalene is not obtained while 45% of l-amino-5- nitronaphthalene and 25% of 2-amino-2'-nitrodiphenyl are formed by reduction of the corresponding dinitro derivatives.

Second-generation aryl isonitrile compounds targeting multidrug-resistant Staphylococcus aureus

Antibiotic resistance remains a major global public health threat that requires sustained discovery of novel antibacterial agents with unexploited scaffolds. Structure-activity relationship of the first-generation aryl isonitrile compounds we synthesized led to an initial lead molecule that informed the synthesis of a second-generation of aryl isonitriles. From this new series of 20 compounds, three analogues inhibited growth of methicillin-resistant Staphylococcus aureus (MRSA) (from 1 to 4 μM) and were safe to human keratinocytes. Compound 19, with an additional isonitrile group exhibited improved activity against MRSA compared to the first-generation lead compound. This compound emerged as a candidate worthy of further investigation and further reinforced the importance of the isonitrile functionality in the compounds’ anti-MRSA activity. In a murine skin wound model, 19 significantly reduced the burden of MRSA, similar to the antibiotic fusidic acid. In summary, 19 was identified as a new lead aryl isonitrile compound effective against MRSA.

Raney Ni-Al alloy-mediated reduction of benzils in wate

Raney Ni-Al alloy in a dilute aqueous alkaline solution has been shown to be a powerful reducing agent and is highly effective for the reduction of alkylbenzils and alkoxybenzils to afford the corresponding 1,2-diarylethers at 90°C, in the absence of organic solvents. 4,4'-Dinitrobenzil was transformed selectively to 1,2-bis(4-aminophenyl) ethane.