1022-22-6

Usage

Uses

Used in Pharmaceutical Industry:
4,4'-DDMU is used as a pharmaceutical intermediate for the synthesis of various drugs and active pharmaceutical ingredients. Its unique structure allows it to serve as a building block in the development of new therapeutic agents, potentially leading to the discovery of novel treatments for various diseases.
Used in Chemical Research:
In the field of chemical research, 4,4'-DDMU is utilized as a research compound to study the properties and reactions of chlorophenylethylene compounds. This helps scientists gain a deeper understanding of the chemical behavior of such compounds and their potential applications in various fields.
Used in Environmental Applications:
4,4'-DDMU can be employed in environmental applications, such as the development of new materials for pollution control or the synthesis of compounds that can help in the remediation of contaminated sites. Its unique structure may offer advantages in these applications, contributing to more effective and sustainable solutions.
Used in Material Science:
In the realm of material science, 4,4'-DDMU can be used as a component in the development of new materials with specific properties. Its incorporation into polymers, for instance, may lead to the creation of materials with improved mechanical, thermal, or chemical properties, depending on the desired application.
Overall, the versatility of 4,4'-DDMU's structure and properties make it a valuable compound for various applications across different industries, from pharmaceuticals to environmental and material sciences. Its potential uses are vast, and ongoing research and development efforts will likely uncover even more ways to harness its unique characteristics for the benefit of society.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 1035, 1950 DOI: 10.1021/ja01158a518

Upstream product

• 56-23-5 tetrachloromethane 
• 72-54-8 1,1-Dichloro-2,2-bis(p-chlorophenyl)ethane 
• 2642-81-1 1,1-bis(p-chlorophenyl)ethene 
• 50-29-3 p,p'-DDT 
• 72-55-9 1,1-bis(4-chlorophenyl)-2,2-dichloroethylene 
• 937-20-2 p-chlorophenacyl chloride 
• 5157-57-3 2,2-dichloro-1-(4-chlorophenyl)ethanone 
• 64-17-5 ethanol 
• 41521-04-4 2,2-dichloro-1-(4-chlorophenyl)ethanol 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 108-90-7 chlorobenzene 
• 90-98-2 4,4'-Dichlorobenzophenone 
• 80268-72-0 2-chloro-1,1-bis-(4-chloro-phenyl)-ethanol 

Downstream Products

• 19685-44-0 [2,2-dichloro-1,1-bis-(4-chloro-phenyl)-ethyl]-methyl ether 
• 19685-45-1 [2-bromo-2-chloro-1,1-bis-(4-chloro-phenyl)-ethyl]-methyl ether 
• 86163-79-3 2,2-dichloro-1,1-bis-(4-chloro-phenyl)-1-formyloxy-ethane 
• 101119-48-6 ethyl-[2,2-dichloro-1,1-bis-(4-chloro-phenyl)-ethyl]-ether 
• 19685-39-3 1,2-dibromo-2-chloro-1,1-bis-(4-chloro-phenyl)-ethane 
• 4681-97-4 1,2,2-trichloro-1,1-bis-(4-chloro-phenyl)-ethane 
• 24337-12-0 2-(4,4'-dichloro-benzhydryl)-[1,3]dioxolane 
• 79133-04-3 1-acetoxy-2,2-dichloro-1,1-bis-(4-chloro-phenyl)-ethane 
• 101273-31-8 (2-chloro-ethyl)-[2,2-dichloro-1,1-bis-(4-chloro-phenyl)-ethyl]-ether 
• 101792-43-2 butyl-[2,2-dichloro-1,1-bis-(4-chloro-phenyl)-ethyl]-ether 
• 130987-49-4 2,2-dichloro-1,1-bis-(4-chloro-phenyl)-1-trichloroacetoxy-ethane 
• 1820-42-4 bis(4-chlorophenyl)acetylene 
• 90-97-1 4,4'-dichlorobenzophenone 
• 2642-82-2 2,2-bis(p-chlorophenyl)ethanol 

Relevant academic research and scientific papers

Enhanced photocatalytic activity of a B12-based catalyst co-photosensitized by TiO2 and Ru(II) towards dechlorination

A novel hybrid photocatalyst denoted as B12-TiO2-Ru(ii) was prepared by co-immobilizing a B12 derivative and trisbipyridine ruthenium (Ru(bpy)32+) on the surface of a mesoporous anatase TiO2 microspheres and was characterized by DRS, XRD, SEM and BET et al. By using the hybrid photocatalyst, DDT was completely didechlorinated and a small part of tridechlorinated product was also detected in the presence of TEOA only after 30 min of visible light irradiation. Under simulated sunlight, the hybrid exhibited a significantly enhanced photocatalytic activity for dechlorination compared with B12-TiO2 under the same condition or itself under visible light irradiation due to the additivity in the contribution of UV and visible part of the sunlight to the electron transfer. In addition, this hybrid catalyst can be easily reused without loss of catalytic efficiency. This is the first report on a B12-based photocatalyst co-sensitized by two photosensitizers with wide spectral response.

Dechlorination of DDT catalyzed by visible-light-driven system composed of vitamin B12 derivative and Rhodamine B

The visible-light-driven dechlorination of 1,1-bis(4-chlorophenyl)-2,2,2- trichloroethane (DDT) was carried out in the presence of a hydrophobic vitamin B12, heptamethyl cobyrinate perchlorate and Rhodamine B. DDT was successfully dechlorinated to form 1,1-bis(4-chlorophenyl)-2,2-dichloroethane (DDD) as the mono-dechlorinated product upon visible light irradiation with a tungsten lamp (λ > 440 nm). Upon prolonged visible light irradiation to DDT, DDMU (1-chloro-2,2-bis(4-chlorophenyl)ethylene), DDMS (1-chloro-2,2-bis(4-chlorophenyl)ethane) and DCS (trans-4,4′- dichlorostilbene) were obtained as the di- and tri-dechlorinated products. The use of the photostable organic sensitizer enabled prolonged photocatalysis via a noble-metal-free process. The vitamin B12 derivative was replaced by an imine/oxime-type cobalt complex although the cobalt complex system showed a lower catalytic activity than the B12 derivative system. The dechlorination mechanism in the B12-Rhodamin B system was investigated by various methods such as UV-vis absorption and fluorescence quenching. Copyright

Mechanochemical reaction of DDT with calcium oxide

Evidence is presented that, in the mechanochemical destruction of DDT [2,2-bis(4-chlorophenyl)1,1,1-trichloroethane] by ball milling in the presence of calcium oxide, a complex series of reactions occurs along the pathway to a product that appears to be essentially graphitic, though aromatic chloro and hydroxy substituents are retained to some degree. The production of the various intermediates can be understood in terms of processes initiated at both CaO and steel (of the milling device) surfaces. With the exception of DOE [2,2-bis(4-chlorophenyl)1,1-dichloroethene], most of these intermediates attain maximum concentrations corresponding to 1 mol % of the original DDT and have been characterized only by their mass spectra. In the case of dichlorotolane [bis(4-chlorophenyl)ethyne], however, yields are sufficient for it to be isolated chromatographically as a pure, crystalline solid and characterized further by NMR spectroscopy. After 12 h of milling, no organic materials volatile enough to be detected by conventional GC/MS procedures are present, but the black, graphitic residue does retain some chlorine that is only slowly removed by extended milling.

Hydrogenation effects in metalloporphycenes: Synthesis and redox behavior of Ni(ii)-tetra(n-propyl)dihydroporphycene

Hydrogenated tetrapropylporphycenes, 2,3-dihydro-2,7,12,17- tetrapropylporphycene 1 and its NiII complex 2, have been prepared and the hydrogenation effects on their electronic structure characterized. A one-electron reduction of 2 promotes dehalogenation of organic halides whose observation is unprecedented for the porphycene compounds.

Synthesis, electrochemistry, spectroelectrochemistry and catalytic properties in DDT reductive dechlorinationin of iron(II) phthalocyanine, 2,3-and 3,4-tetrapyridinoporphyrazine complexes

Iron(II) 2,3-and 3,4-tetrapyridinoporphyrazine complexes (2,3-PyD and 3,4-PyD) were synthesized and characterized as to their electrochemistry, UV-visible spectroelectrochemistry and catalytic properties towards the reductive dechlorination of 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethane (p,p′-DDT) in pyridine, dimethyl sulfoxide (DMSO), N,N′- dimethylacetamide (DMA) and N,N′-dimethylformamide (DMF). These properties were compared with those of the unsubstituted iron(II) phthalocyanine ((Pc)Fe). Electrochemistry indicates that there are up to three reductions and one oxidation in the three investigated derivatives. The easiest reduction takes place for 3,4-PyD while the most difficult one occurs for (Pc)Fe in all of the solvents investigated. The first reduction is metal-centered corresponding to the formation of [P(-2)Fe(I)]- while the second and third reductions are ring-centered leading stepwise to the generation of [P(-3)Fe(I)] 2- · and [P(-4)Fe(I)]3-, where P = phthalocyanine or tetrapyridinoporphyrazine rings. Aggregation exists in the solutions of all three iron complexes and its extent depends upon the nature and concentration of the iron compounds and the binding property of each solvent. The order of the extent of aggregation for the three iron derivatives is 3,4-PyD > 2,3-PyD > (Pc)Fe. Stronger binding solvents such as pyridine and DMSO do not favor the aggregation. The singly and doubly reduced species of investigated complexes, [P(-2)Fe(I)]- and [P(-3)Fe(I)]2- ·, are active in DDT reductive dechlorination, the latter of which has better catalytic performance. As a result, three products, 1,1-bis(4-chlorophenyl)-2,2- dichloroethane (p,p′-DDD), 1,1-bis(4-chlorophenyl)-2,2-dichloroethylene (p,p′-DDE), and 1,1-bis(4-chlorophenyl)-2-chloroethylene (p,p′-DDMU), were obtained after the dechlorination of DDT catalyzed by each iron complex. The increasing order of catalytic performance is 3,4-PyD 2,3-PyD (Pc)Fe in pyridine, which is superior to DMSO and DMA for the DDT dechlorination reaction. An overall electrocatalytic mechanism is proposed for DDT reductive degradation based on the electrochemical and UV-visible spectroelectrochemical results.

Synthesis of a B12-BODIPY dyad for B12-inspired photochemical transformations of a trichloromethylated organic compound

A B12complex-BODIPY dyad was synthesized by peripheral modification of cobalamin derivatives. The photophysical properties of the dyad were investigated by UV-vis, PL, and transient absorption spectroscopy. A visible light-driven dechlorination reaction of a trichlorinated organic compound, DDT, was reported. The dyad showed efficient catalysis for dechlorination under N2with turnover numbers of over 220 for the reaction. One-pot syntheses of an ester and amide from DDT and benzotrichloride were also achieved using the dyad under air.

Kinetic Behavior of Cetyltrimethylammonium Hydroxyde. The Dehydrochlorination of 1,1,1-Trichloro-2,2-bis(p-chlorophenyl)ethane and Some of Its Derivatives.

The dehydrochlorination of 1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane (DDT), 1,1-dichloro-2,2-bis(p-chlorophenyl)ethane (DDD), and 1-chloro-2,2-bis(p-chlorophenyl)ethane (DDM) with hydroxide ion was studied in the presence of hexadecyltrimethylammonium hydroxide (CTAOH) micelles at 25.0 deg C.The experimental results clearly deviate from the theoretical behavior expected by the pseudophase-ion-exchange model and can be explained by considering an additional reaction pathway across the micellar boundary.This additional reaction pathway in which hydroxide ion in the aqueous phase reacts directly with the organic substrate in the micelle is probably of a phase-transfer catalysis type.

Use of Relative Counterion Type Micelles for the Determination of Selectivity Coefficients

Monovalent/monovalent and divalent/monovalent ion exchange in hexadecyltrimethylammonium hydroxide (CTAOH), a relative counterion type micelle, was investigate by using as a probe the dehydroshlorination reactions of 1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane (DDT) and 1,1-dichloro-2,2-bis(p-chlorophenyl)ethane (DDD).Selectivity coefficients for the ion exchange of bromide, chloride, fluoride, nitrate, acetate, sulfate, and carbonate anions with the reactive counterion (OH-) and between the anions themselves were evaluated from the kinetic treatment of the data using a simple pseudophase ion-exchange-type formalism.

Electrolytic Dechlorination of DDT In a Bicontinuous Microemulsion

Electrolytic reduction in a bicontinuous microemulsion of surfactant, oil, and water removed aliphatic and aromatic chlorines from DDT. Microemulsions of didodecyldimethylammonium bromide/dodecane/water used with graphite felt cathodes provided a less expensive, less toxic approach to DDT electrolysis compared to using conventional organic solvents and metal electrodes. Good rates of aliphatic dechlorination were achieved by applying -1 V vs. Ag/AgBr and using the catalyst Co(bpy)32+, but the best yield (34 percent in 3 hr) of the fully dechlorinated hydrocarbon 1,1-diphenylethane was achieved by using -2 V with oxygen in the reaction medium.

Limitations of the Pseudophase Model of Micellar Catalysis. The Dehydrochlorination of 1,1,1-Trichloro-2,2-bis(p-chlorophenyl)ethane and Some of Its Derivatives

The dehydrochlorination of 1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane (DDT), 1,1-dichloro-2,2-bis(p-chlorophenyl)ethane (DDD), and 1-chloro-2,2-bis(p-chlorophenyl)ethane (DDM) with hydroxide ion was studied in the presence of hexadecyltrimethylammonium bromide (CTAB) micelles at 25.0 deg C.The experimental results indicate that there is good agreement between the experimental results and theoretical models of micellar catalysis for (OH) in the range of 1E-3-1E-2 M.For (OH) values higher than 1E-2 M, the pseudophase model fails there is a significant deviation between the theoretically calculated and observed values of the pseudo-first-order rate constant.The experimental results can be explained by considering an additional reaction pathway across the micellar boundary, in which hydroxide ion in the aqueous phase reacts directly with the organic substrate in the micelle.This additional reaction pathway is probably of a phase transfer catalysis type.