935-04-6

Basic information

• Product Name: BenzylVinylEther
• Synonyms: BenzylVinylEther;Vinyloxymethyl-benzene;1-(Benzyloxy)ethene;Benzyl ethenyl ether;Vinyl benzyl ether;Benzene,[(ethenyloxy)methyl]-
• CAS NO: 935-04-6
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.1751
• Mol File: 935-04-6.mol

Chemical Properties

• Boiling Point: 198.256°C at 760 mmHg
• Flash Point: 67.498°C
• Appearance: /
• Density: 0.957g/cm³
• Vapor Pressure: 0.512mmHg at 25°C
• Refractive Index: 1.51
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: BenzylVinylEther(CAS DataBase Reference)
• NIST Chemistry Reference: BenzylVinylEther(935-04-6)
• EPA Substance Registry System: BenzylVinylEther(935-04-6)

Safety Data

• Hazardous Substances Data: 935-04-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Benzyl vinyl ether is used as a precursor in organic synthesis for its ability to participate in a wide range of chemical reactions. Its reactivity allows it to be a key component in the formation of complex organic molecules.
Used in Polymerization Processes:
As a monomer, benzyl vinyl ether is utilized in polymerization processes to create polymers with specific properties. Its incorporation into polymer chains can influence the material's characteristics, such as flexibility, strength, and reactivity.
Used as a Crosslinking Agent:
Benzyl vinyl ether is employed as a crosslinking agent in the production of polymeric materials. It helps in creating a network structure within the polymer, enhancing the material's stability and performance.
Used in the Synthesis of Specialty Chemicals:
Benzyl vinyl ether serves as a building block in the synthesis of specialty chemicals, contributing to the development of unique chemical products with tailored properties for specific applications.
Used in Industrial Applications:
While the specific industrial applications are not detailed in the provided materials, benzyl vinyl ether's role as a versatile chemical intermediate suggests its use across various industries that rely on polymers and specialty chemicals for their products.

InChI:InChI=1/C9H10O/c1-2-10-8-9-6-4-3-5-7-9/h2-7H,1,8H2

Upstream product

• 4392-27-2 1-phenyl-3-chloro-1,2-epoxypropane 
• 60633-79-6 1-bromo-3-phenyl-2-epoxypropane 
• 109-92-2 ethyl vinyl ether 
• 100-51-6 benzyl alcohol 
• 340160-89-6 C₂₂H₂₃NO₃S₂ 
• 33100-27-5 15-crown-5 
• 556-52-5 oxiranyl-methanol 
• 100-39-0 benzyl bromide 
• 74-85-1 ethene 
• 111-34-2 -butyl vinyl ether 
• 21175-64-4 1,1-dideuteriophenylmethanol 
• 75-20-7 calcium carbide 
• 4392-24-9 Cinnamyl bromide 
• 121-45-9 phosphorous acid trimethyl ester 

Downstream Products

• 66222-24-0 acetaldehyde ethyl benzyl acetal 
• 66695-78-1 acetaldehyde-(benzyl-butyl-acetal) 
• 30830-27-4 3-benzyloxy cyclobutanone 
• 69520-20-3 (E)-1-Phenyl-2-(phenylmethoxy)ethene 
• 25109-98-2 α-(benzyloxy)styrene 
• 99789-09-0 r-2-Benzyloxy-3,4-dihydro-c-4-methoxy-6-methyl-2H-pyran-5-carbonsaeure-methylester 
• 99789-09-0 r-2-Benzyloxy-3,4-dihydro-t-4-methoxy-6-methyl-2H-pyran-5-carbonsaeure-methylester 
• 141258-54-0 acetaldehyde benzyl 1,2,3,6-tetrahydrobenzyl acetal 
• 142362-53-6 2-benzyloxy-4-phthalimido-6-trichloromethyl-3,4-dihydro-2H-pyran 
• 142362-53-6 (2SR,4SR)-2-benzyloxy-4-phthalimido-6-trichloromethyl-3,4-dihydro-2H-pyran 
• 142362-54-7 (2SR,4RS)-2-benzyloxy-4-phthalimido-6-trichloromethyl-3,4-dihydro-2H-pyran 
• 127032-97-7 (4R,6R)-1-Benzenesulfonyl-6-benzyloxy-4-phenyl-1,4,5,6-tetrahydro-pyridine-2-carboxylic acid ethyl ester 
• 127032-97-7 (2R^*,4S^*)-2-(benzyloxy)-6-(ethoxycarbonyl)-4-phenyl-1-(phenylsulfonyl)-1,2,3,4-tetrahydropyridine 
• 130146-85-9 (2R^*,4S^*)-2-(benzyloxy)-4-(ethoxycarbonyl)-1-(phenylsulfonyl)-1,2,3,4-tetrahydropyridine 

Relevant articles and documents

Direct Synthesis of Deuterium-Labeled O -, S -, N-Vinyl Derivatives from Calcium Carbide

A novel methodology for the preparation of trideuterovinyl derivatives of high purity directly from alcohols, thiols, and NH-compounds was developed. Commercially available calcium carbide and D 2 O acted as a D 2 -acetylene source, and DMSO- d 6 was used to complete the formation of the D 2 C=C(D)-X fragment (X = O, S, N). Polymerization of a selected trideuterovinylated compound showed a very promising potential of these substances in the synthesis of labeled polymeric materials. Biological activity of the synthesized trideuterovinyl derivatives was evaluated and the results indicated a significant increase of cytotoxicity upon deuteration.

N,N-Dimethylformamide-stabilised palladium nanoparticles combined with bathophenanthroline as catalyst for transfer vinylation of alcohols from vinyl ether

We reportN,N-dimethylformamide-stabilised Pd nanoparticle (Pd NP)-catalysed transfer vinylation of alcohols from vinyl ether. Pd NPs combined with bathophenanthroline exhibited high catalytic activity. This reaction proceeded with low catalyst loading and the catalyst remained effective even after many rounds of recycling. The observation of the catalyst using transmission electron microscopy and dynamic light scattering implied no deleterious aggregation of Pd NPs.

Method for preparing benzyl vinyl ether and monomer copolymer thereof

The invention belongs to the field of fine chemical synthesis, and relates to a method for preparing benzyl vinyl ether and a monomer copolymer thereof. Benzyl vinyl ether is prepared from benzyl alcohol and acetylene under the catalysis of a catalyst in a low-pressure, heating and stirring environment, and then hydroxyalkyl ether, fluoro-olefin and an initiator are added to prepare the benzyl vinyl ether copolymer. The yield of benzyl vinyl ether prepared by the method is as high as 51-85%, the purity is as high as 98.0%-99.9%, and the yield of the benzyl vinyl ether copolymer is 80%-99.5%. Moreover, production equipment of the preparation method is conventional equipment, the used catalyst is cheap, the catalyst is not easy to inactivate in the reaction process, reaction conditions are mild and easy to implement, operation is convenient, and the preparation method is suitable for industrial production.

Preparation method of bilastine intermediate

The invention relates to a preparation method of a bilastine intermediate represented by a formula 1. The preparation method specifically comprises: carrying out a reaction in a first solvent in the presence of DBU by using 2-bromoethyl anisole (formula I

Calcium Carbide Looping System for Acetaldehyde Manufacturing from Virtually any Carbon Source

A vinylation/devinylation looping system for acetaldehyde manufacturing was evaluated. Vinylation of iso-butanol with calcium carbide under solvent-free conditions was combined with hydrolysis of the resulting iso-butyl vinyl ether under slightly acidic conditions. Acetaldehyde produced by hydrolysis was collected from the reaction mixture by simple distillation, and the remaining alcohol was redirected to the vinylation step. All the inorganic co-reagents can be looped as well, and the full sequence is totally sustainable. A complete acetaldehyde manufacturing cycle was proposed on the basis of the developed procedure. The cycle was fed with calcium carbide and produced the aldehyde as a single product in a total preparative yield of 97 %. No solvents, hydrocarbons, or metal catalysts were needed to maintain the cycle. As calcium carbide in principle can be synthesized from virtually any source of carbon, the developed technology represents an excellent example of biomass and waste conversion into a valuable industrial product.

Stereoselective three-component cascade synthesis of α-substituted 2,4-dienamides from: gem -difluorochloro ethanes

Herein, we describe a new transition metal-free Claisen rearrangement for the synthesis of α-substituted 2,4-dienamides. The one-pot, stereoselective three-component cascade reaction between a series of propargyl alcohols, amines, and gem-difluorochloro ethane derivatives afforded various polysubstituted 2,4-dienamides in good yields. This synthetic method for 1,1-captodative dienes, α-substituted 2,4-dienamides, can be utilized for preparing pharmaceutical analogues containing an indolin-2-one or lactone moiety.

Synthesis of Piperidine Derivatives by Rhodium- Catalyzed Tandem Reaction of N-Sulfonyl-1,2,3-Triazole and Vinyl Ether

A chemoselective tandem reaction of 4-acyloxymethylene-1-sulfonyl-1,2,3-triazole and vinyl ether was reported, producing polysubstituted piperidine derivatives in up to 96% yield. The key intermediate N-sulfonyl 1-azadiene generated by migration of the OAc group to the α-imino rhodium carbene was isolated and a plausible mechanism was proposed. Several related ring systems were constructed from the highly functionalized products. (Figure presented.).

Access to α-Amino Acid Esters through Palladium-Catalyzed Oxidative Amination of Vinyl Ethers with Hydrogen Peroxide as the Oxidant and Oxygen Source

A novel and convenient palladium catalytic system for the synthesis of α-amino acid esters from simple starting materials is reported. Hydrogen peroxide not only acts as the green oxidant, but also as the oxygen source. This strategy for the conversion of amines and vinyl ethers into highly functionalized and structurally diverse α-amino acid esters is characterized by the simplicity of the experimental procedure, mild reaction conditions, high atom economy, scalability, and practicability.

A solid acetylene reagent with enhanced reactivity: Fluoride-mediated functionalization of alcohols and phenols

The direct vinylation of an OH group in alcohols and phenols was carried out utilizing a novel CaC2/KF solid acetylene reagent in a simple K2CO3/KOH/DMSO system. The functionalization of a series of hydroxyl-group-containing substrates and the post-modification of biologically active molecules were successfully performed using standard laboratory equipment, providing straightforward access to the corresponding vinyl ethers. The overall process developed involves an atom-economical addition reaction employing only inorganic reagents, which significantly simplifies the reaction set-up and the isolation of products. A mechanistic study revealed a dual role of the F- additive, which both mediates the surface etching/renewal of the calcium carbide particles and activates the CC bond towards the addition reaction. The development of the fluoride-mediated nucleophilic addition of alcohols eliminates the need for strong bases and may substantially extend the areas of application of this attractive synthetic methodology due to increasing functional group tolerance. As a replacement for dangerous and difficult to handle high-pressure acetylene, we propose the solid reagent CaC2/KF, which is easy to handle, does not require dedicated laboratory equipment and demonstrates enhanced reactivity of the acetylenic triple bond. Theoretical calculations have shown that fluoride-mediated activation of the hydroxyl group towards nucleophilic addition significantly reduces the activation barrier and facilitates the reaction.

METHOD OF PRODUCING VINYL ETHER, AND CATALYST FOR ETHER EXCHANGE REACTION

PROBLEM TO BE SOLVED: To provide a method for producing vinyl ether that allows a reaction to sufficiently proceed even in a small amount of catalyst, and facilitates the recovery and reuse of the catalyst with excellent operability. SOLUTION: A method for producing vinyl ether represented by formula (3) is characterized in that alcohol and vinyl ether represented by formula (2) are subjected to ether replacement reaction. There is also provided catalyst that comprises a metal nano cluster obtained by heating a transition metal compound in solvent comprising coordination organic solvent and a nitrogen-containing heterocyclic compound. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT