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

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

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 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 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 
• 6067-45-4 4,4'-dinitrobenzil 
• 65198-02-9 3-(4-aminophenyl)-acrylic acid methyl ester 
• 461461-89-2 4-aminocinnamyl alcohol 
• 621-82-9 Cinnamic acid 
• 2393-18-2 p-aminocinnamic acid 

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 
• 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) 
• 159428-10-1 C₅₀H₄₂N₂P₂ 

Relevant articles and documents

Diphenyl ethane diisocyanate and preparation method thereof

The invention discloses diphenyl ethane diisocyanate and a preparation method thereof, and relates to the technical field of high molecular material monomer preparation. The diphenylethane diisocyanate has a structure shown in the specification, wherein R is H or alkyl, and a substituent R is positioned at a 2 (2') site or a 3 (3') site; substituent -NCO is located at a 4 (4') site or a 5 (5') site or a 6 (6') site; EDI serves as a polyurethane monomer to be applied to polyurethane materials and comprises polyurethane foam, a polyurethane adhesive, polyurethane synthetic leather, a polyurethane fabric coating layer, a polyurethane resin coating, a polyurethane elastomer and other synthetic materials.

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.

Ultrahigh performance bio-based polyimides from 4,4′-diaminostilbene

We have developed a novel route for the synthesis of high-performance bio-polyimides (PIs) microbially-derived from photo-responsive aromatic diamine 4,4′-diaminostilbene (DAS) and its reduced counterpart 4, 4′-(ethane-1,2-diyl)dianiline (EDDA). DAS and EDDA were condensed with various commercially-available dianhydrides to obtain a series of poly(amic acid)s (PAAs) and PIs which were characterized in terms of their thermal, mechanical, and photo-functions. These bio-based PAAs showed a very high viscosity of 6.62 dL/g, and the PIs showed ultrahigh thermal resistance with Td10 values over 600 °C, which were higher than that of any bio-based plastic reported thus far. They also showed Tg values above 250 °C, and tensile strength of over 132 MPa, which is higher than that of Kapton. The PIs also showed photo-functional behavior based on stilbene-based photoreactions.

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.

Salt suitable for an acid generator and a chemically amplified positive resist composition containing the same

The present invention provides a salt represented by the formula (I): wherein P1, P2 and P3 each independently represent a C1-C30 alkyl group which may be substituted with at least one selected from a hydroxyl group, a C3-C12 cyclic hydrocarbon group and a C1-C12 alkoxy group, or a C3-C30 cyclic hydrocarbon group which may be substituted with at least one selected from a hydroxyl group and a C1-C12 alkoxy group, provided that all of P1, P2 and P3 are not simultaneously phenyl groups which may be substituted, Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, and R represents a group represented by the formula: wherein A1 represents —OH or —Y1—OH, n represents an integer of 1 to 9, and Y1 represents a divalent C1-C6 saturated aliphatic hydrocarbon group; a group represented by the formula: wherein ring X1 represents a C3-C30 monocyclic or polycyclic hydrocarbon group in which one —CH2— group is substituted with —CO—, and at least one hydrogen atom in the monocyclic or polycyclic hydrocarbon group may be substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C4 perfluoroalkyl group, a C1-C6 hydroxyalkyl group, a hydroxyl group or a cyano group; a group represented by the formula: wherein ring X2 represents a C3-C30 monocyclic or polycyclic hydrocarbon group in which a hydrogen atom of one —CH2— group is substituted with a hydroxyl group, and at least one hydrogen atom in the monocyclic or polycyclic hydrocarbon group may be substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C4 perfluoroalkyl group, a C1-C6 hydroxyalkyl group, a hydroxyl group or a cyano group; a group represented by the formula: wherein ring X3 represents a C3-C30 monocyclic or polycyclic hydrocarbon group in which one —CH2— group is substituted with —COO—, and at least one hydrogen atom in the monocyclic or polycyclic hydrocarbon group may be substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C4 perfluoroalkyl group, a C1-C6 hydroxyalkyl group, a hydroxyl group or a cyano group, and m represents an integer of 0 to 12; or a group represented by the formula: wherein ring X4 represents a C6-C30 polycyclic hydrocarbon group having tricycle or more, and at least one hydrogen atom in the polycyclic hydrocarbon group may be substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C4 perfluoroalkyl group, a C1-C6 hydroxyalkyl group or a cyano group, and l represents an integer of 1 to 12. The present invention further provides a chemically amplified resist composition comprising the salt represented by the above-mentioned formula (I).

Functionalized Photoreactive Compounds

The present invention concerns functionalized photoreactive compounds of formula (I), that are particularly useful in materials for the alignment of liquid crystals. Due to the adjunction of an electron withdrawing group to specific molecular systems bearing an unsaturation directly attached to two unsaturated ring systems, exceptionally high photosensitivities, excellent alignment properties as well as good mechanical robustness could be achieved in materials comprising said functionalized photoreactive compounds of the invention.

Synthesis and Fungicidal Activity of Novel 4,4′-Bis(2″ -aryl-5″-methyl/unsubstituted-4″-oxo-thiazolidin-3″-yl) Bibenzyl

Reduction followed by nitration of benzil I yielded 4,4′- dinitrobibenzyl (III) which by reduction furnished quantitatively and analytically pure 4,4′-diaminobibenzyl (IV) which on condensation with different carbonyl compounds gave 4,4′-bis (benzylideneamino) bibenzyls (Va-f). Compounds (Va-f) on cycloaddition with mercaptoacetic acid/2-mercaptopropionic acid yielded the corresponding 4-oxothiazolidin-3-yl bibenzyls (Vla-I). The compounds VIg-I have two chiral centers in each thiazolidinone moiety so two diastereomers are possible, but on crystallization and repeated chromatography, one diastereomer was obtained. The absolute configuration of the diastereomer was tentatively assigned on the basis of 1H NMR spectra. 1H NMR spectra of the product showed a distinct doublet at δ 1.22 for C5-CH3 of thiazolidinone ring (22, 23) and a distinct quartet at δ4.20 for the C5-H proton. Similarly, the C2 proton showed an independent singlet at δ 5.95, so the diastereomers obtained were assigned trans configuration. Compounds Va-f and Vla-I were evaluated in vitro for their fungitoxicities against Fusarium oxysporium and Penicillium citrinum. All the compounds were found to be antifungal active. Some of the compounds displayed activities comparable with that of the commercial fungicide Dithane M-45. Structure-activity relationships for the screened compounds are discussed.

Synthesis and preliminary testing of molecular wires and devices

Presented here are several convergent synthetic routes to conjugated oligo(phenylene ethynylene)s. Some of these oligomers are free of functional groups, while others possess donor groups, acceptor groups, porphyrin interiors, and other heterocyclic interiors for various potential transmission and digital device applications. The syntheses of oligo(phenylene ethynylene)s with a variety of end groups for attachment to numerous metal probes and surfaces are presented. Some of the functionalized molecular systems showed linear, wire-like, current versus voltage (I(V)) responses, while others exhibited nonlinear I(V) curves for negative differential resistance (NDR) and molecular random access memory effects. Finally, the syntheses of functionalized oligomers are described that can form self-assembled monolayers on metallic electrodes that reduce the Schottky barriers. Information from the Schottky barrier studies can provide useful insight into molecular alligator clip optimizations for molecuar electronics.

Indium metal as a reducing agent in organic synthesis

The low first ionisation potential (5.8 eV) of indium coupled with its stability towards air and water, suggest that this metallic element should be a useful reducing agent for organic substrates. The use of indium metal for the reduction of C=N bonds in imines, the heterocyclic ring in benzo-fused nitrogen heterocycles, of oximes, nitro compounds and conjugated alkenes and the removal of 4-nitrobenzyl protecting groups is described. Thus the heterocyclic ring in quinolines, isoquinolines and quinoxalines is selectively reduced using indium metal in aqueous ethanolic ammonium chloride. Treatment of a range of aromatic nitro compounds under similar conditions results in selective reduction of the nitro groups; ester, nitrile, amide and halide substituents are unaffected. Likewise indium in aqueous ethanolic ammonium chloride is an effective method for the deprotection of 4-nitrobenzyl ethers and esters. Indium is also an effective reducing agent under non-aqueous conditions and α-oximino carbonyl compounds can be selectively reduced to the corresponding N-protected amine with indium powder, acetic acid in THF in the presence of acetic anhydride or di-tert-butyl dicarbonate. Conjugated alkenes are also reduced by indium in THF-acetic acid.