105-06-6

Basic information

• Product Name: P-DIVINYLBENZENE 85
• Synonyms: 1,4-diethenyl-benzen;1,4-diethenylbenzene;1,4-diethenyl-Benzene;benzene,1,4-diethenyl-;p-vinylstyrene;P-DIVINYLBENZENE 85;PARA-DIVINYLBENZENE;1,4-Bisethenylbenzene
• CAS NO: 105-06-6
• Molecular Formula: C₁₀H₁₀
• Molecular Weight: 130.1864
• EINECS: 203-266-8
• Product Categories: Biocompatible/Biodegradable Materials;CrosslinkersMaterials Science;Crosslinking Agents;Polymer Additives;Polymer Science;Biomaterials;Crosslinkers;Crosslinking Agents;Materials Science;Polymer Science;Reagents for Polymerization
• Mol File: 105-06-6.mol

Chemical Properties

• Melting Point: 31°C
• Boiling Point: 175.9°C (rough estimate)
• Flash Point: 148 °F
• Appearance: /
• Density: 0.914 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.256mmHg at 25°C
• Refractive Index: n20/D 1.5470(lit.)
• Storage Temp.: ?70°C
• Water Solubility: 1μg/L
• CAS DataBase Reference: P-DIVINYLBENZENE 85(CAS DataBase Reference)
• NIST Chemistry Reference: P-DIVINYLBENZENE 85(105-06-6)
• EPA Substance Registry System: P-DIVINYLBENZENE 85(105-06-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-43
• Safety Statements: 7-23-26-36-45-36/37
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 105-06-6(Hazardous Substances Data)

Usage

Uses

Used in Water Remediation:
P-Divinylbenzene 85 is used as a cross-linking agent for the formation of new microporous nanocomposites in water remediation. The combination of DVB with styrene/vinylbenzene chloride and multi-walled carbon nanotubes (MWCNTs) results in advanced materials that can effectively address water contamination issues.
Used in Electrolytic Materials for Lithium Batteries:
In the energy storage industry, P-Divinylbenzene 85 is used as a component in the creation of electrolytic materials for lithium batteries. By forming linkages with polyethylene oxide (PEO) through the use of polyethylene glycol diacrylate, DVB contributes to the development of improved battery performance and energy efficiency.
Used in Polymeric Processes:
P-Divinylbenzene 85 is used as a cross-linking agent in various polymeric processes, such as the copolymerization of styrene. This application enhances the thermo-mechanical properties of the resulting composite materials, making them more suitable for a range of industrial applications.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H10/c1-3-9-5-7-10(4-2)8-6-9/h3-8H,1-2H2

Upstream product

• 25393-98-0 1,4-bis(1,2-dibromoethyl)benzene 
• 6781-43-7 1,4-bis(1-hydroxyethyl)benzene 
• 5140-03-4 2-[4-(2-hydroxyethyl)phenyl]ethan-1-ol 
• 16323-43-6 1,4-phenylenediacrylic acid 
• 108124-68-1 α,α'-dimethyl-1,4-benzenedimethanol diacetate 
• 50-00-0 formaldehyd 
• 47861-54-1 1,4-Bis-[(triphenyl-λ⁵-phosphanylidene)-methyl]-benzene 
• 2499-63-0 4-(2-bromoethyl)styrene 
• 917-64-6 methyl magnesium iodide 
• 69922-37-8 2,2'-p-phenylene-bis-[1,3]dithiolane 
• 1610-51-1 tricyclo[6.2.0.0^3,6]deca-1,3⁽⁶⁾,7-triene 
• 106-37-6 1.4-dibromobenzene 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 36262-33-6 dispiro<2.2.2.2>deca-4,9-diene 

Downstream Products

• 25393-98-0 1,4-bis(1,2-dibromoethyl)benzene 
• 17194-87-5 1,4-bis(1'-bromoethyl)benzene 
• 95386-10-0 4-(1,2-dibromo-ethyl)-styrene 
• 17480-55-6 1,4-bis(2,2-dichlorocyclopropyl)benzene 
• 64740-43-8 1,4-bis-(2-phenylsulfanyl-ethyl)-benzene 
• 22535-76-8 1,4-Bis-<2-phenylphosphino-ethyl>-benzol 
• 129371-24-0 1,1,2,2-Tetracyano-3-(p-vinylphenyl)cyclobutane 
• 100-21-0 terephthalic acid 
• 1075-49-6 4-ethenylbenzoic acid 
• 1791-26-0 4-vinyl-benzaldehyde 
• 623-27-8 terephthalaldehyde, 
• 141839-25-0 N-(p-methoxybenzyl)-p-vinylphenethylamine 
• 141839-24-9 N-(p-methylbenzyl)-p-vinylphenethylamine 
• 127635-89-6 cis-1,2-bis(p-vinylphenyl)cyclobutane 

Relevant articles and documents

New Arylene-Germylene-Vinylene Compounds: Stereoselective Synthesis, Characterization, and Photophysical Properties

The stereoselective route toward new molecular and macromolecular compounds containing arylene-germylene-vinylene units is described. The reagents for germylative coupling reaction were 1,4-bis(dimethylvinylgermyl)benzene (1) and vinyl- and divinylarenes

A new class of stereoregular vinylene-arylene copolymers with double-decker silsesquioxane in the main chain

A synthesis of a new macromolecular class of vinylene-arylene copolymers with double-decker silsesquioxane in the main chain is presented. Two transition-metal-catalyzed processes, which is silylative-coupling copolycondensation (SCC) and ADMET copolymerization of divinyl-substituted double-decker silsesquioxanes (DDSQ-2SiVi) with selected diolefins, are reported to be highly efficient tools for the formation of stereoregular copolymers containing DDSQ-silylene-vinylene-arylene units. The copolymeric products are studied in terms of their structural, thermal, and mechanical properties.

Living anionic polymerization of 1,4-divinylbenzene and its isomers

The anionic polymerization of 1,4-divinylbenzene (1) and its ortho (2) and meta isomers (3) were studied under a variety of conditions. One of the two vinyl groups of 1 was selectively and exclusively polymerized in a living manner by the addition of a suitable additive under the conditions of -78 C for 1 min and -95 C for 30 min. Under such conditions, the unwanted addition reaction of the chain-end anion to the pendant vinyl group was almost suppressed and soluble polymers with predictable molecular weights of up to 60 500 g/mol and narrow molecular weight distributions (Mw/Mn 1.05) were quantitatively obtained. The amount of dimerized chain produced by the addition reaction was negligible or very small (5%). The effective additives in the polymerization involve potassium alkoxides and phenoxides, derived from tert-butyl alcohol, sec-butyl alcohol, 2,4-dimethyl-3-pentanol, 1-methylcyclohexanol, 1:2,5:6-di-O-isopropylidene-α-d-glucofuranose, phenol, 1-naphthol, and 2,6-di(tert-butyl)-4-methylphenol, and potassium carboxylate derived from pivalic acid. The living polymer of 1 was not stable at -78 C after 5 min or longer times, but very stable at -95 C even for 30 min. The chain-end anion could be stabilized by end-capping with tert-butyl methacrylate and 1,1-diphenylethylene, and the resulting anions remained unchanged at -78 C even after several hours.

New synthetic applications of indium organometallics in cross-coupling reactions

The use of indium organometallics in multifold and sequential cross-coupling reactions is reported. Triorganoindium reagents (R3In) react, under palladium catalysis, with oligohaloarenes affording the multiple cross-coupling products in a single operation. In the reaction, the three organic groups (alkyl, aryl, alkenyl or alkynyl) attached to indium are efficiently transferred to the electrophile, with only a slight excess of organometallic reagent. We demonstrate that indium organometallics are useful reagents for sequential cross-coupling reactions. This reaction illustrates the high chemoselectivity of R3In. Georg Thieme Verlag Stuttgart.

Synthesis of core cross-linked star polymers consisting of well-defined aromatic polyamide arms

Homopolymer-arm, block-arm, and miktoarm star polymers consisting of poly(N-octylm-benzamide) and poly(N-H-m-benzamide) were synthesized by means of a core cross-linking method. Macromonomers (MM) with the styryl terminal moiety were synthesized by chain-growth condensation polymerization of 3-(alkylamino)benzoic acid esters 1 in the presence of phenyl 4-vinylbenzoate as an initiator, and copolymerization with N,N'-methylenebis(acrylamide) as a divinyl monomer in the presence of 2,2'-azobis(isobutyronitrile) at 60 °C yielded the corresponding star polymers. In the synthesis of star polymers containing poly(N-H-m-benzamide) arms, the 4-(octyloxy)benzyl group on the amide nitrogen of the obtained star polymers was removed with trifluoroacetic acid. The number of arms per molecule, determined by multiangle laser light scattering, varied in the range of 36-100 depending on the N-alkyl group of 1 and the molecular weight of MM. The 1H NMR spectra of the star polymers in dimethyl sulfoxide revealed that the poly(N-octyl-m-benzamide) segments and arms of the block-arm and miktoarm star polymers, respectively, were compactly packed at room temperature and became extended at higher temperatures.

New heck-type coupling reactions of natural tetrapyrroles - Synthesis of porphyrinoligomers bridged by divinyl- and trivinylbenzene

Using palladium(0)-catalyzed coupling reactions we were able to synthesize mono-, di-, and trimeric porphyrins linked by di- and trivinylbenzenes. The reactions were carried out with palladium(II) acetate in DMF under phase-transfer conditions. These coupling conditions are new in the field of porphyrin chemistry and proved to be a useful tool in the synthesis of C-C linked oligomeric porphyrins, as these compounds can be obtained in a simple one pot reaction with good yields.

Fluorescent sensor based on a novel conjugated polyfluorene derivative

A novel water-soluble polyfluorene derivative, poly[(9,9-bis(3′-((N, N-dimethylamino)N-ethylammonium)propyl)-2,7-fluorene)-alt-2,7-(9, 9-p-divinylbenzene)]dibromide (P-2) was synthesized by the palladium-catalyzed Suzuki coupling reaction and it's quaternized ammonium polyelectrolyte derivatives was obtained through a postpolymerization treatment on the terminal amino groups. The electrochemical and optical properties of the copolymers was fully investigated. The results showed that the new polyfluorene derivative had high electronic conductivity and strong fluorescence, therefore it had good potential to be used in chemical and biological sensors, as shown in optical sensing of bovine albumin (BSA) in this study.

Catalytic chain transfer mediated autopolymerization of divinylbenzene: Toward facile synthesis of high alkene functional group density hyperbranched materials

A facile and highly reproducible autopolymerization method, mediated by catalytic chain transfer, for the synthesis of hyperbranched materials with high alkene functional group density is reported. The rapid autopolymerization of divinylbenzene at 150 °C in the absence of any catalytic chain transfer agent was demonstrated to result in the formation of highly cross-linked networks/gels in less than 10 min. Exploitation of the extremely high chain transfer coefficient of bis[(difluoroboryl)diphenylglyoximato]cobalt(II) delayed gelation and produced good yields of high molecular weight hyperbranched divinylbenzene in under 1 h on a multigram scale. Gas chromatography was employed to monitor the levels of conversion over the course of the reaction. The materials produced were characterized by GPC, MALLS, and viscometry.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent

A nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used, making this protocol more attractive from the point of view of green chemistry.

Copper-Catalyzed Defluorinative Hydroarylation of Alkenes with Polyfluoroarenes

A catalytic defluorinative hydroarylation of alkenes with polyfluoroarenes in the presence of dppbz-ligated Cu catalyst and silanes was developed. This method provides a straightforward and alternative avenue to synthetic important polyfluorinated arenes with readily available and bench-stable alkenes as latent nucleophiles, and therefore avoids conventional reliance on stoichiometric quantities of organometallic reagents. This reaction proceeds under very mild conditions and exhibits good functional group compatibility and high level of regioselectivity. The synthetic potential of this method was further demonstrated by a gram-scale synthesis, and an array of experimental studies were also carried out to elaborate the probable mechanism.