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113538-80-0

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113538-80-0 Usage

General Description

4-Vinylbenzyl glycidyl ether is a chemical compound often used in the production of polymers due to its unique characteristics, such as its ability to react with a wide range of functional groups. It is utilized in a variety of industries, particularly in the manufacturing of plastics, resins, and coatings, among many others. This chemical is classified as an ether and possesses an aromatic ring and epoxy functional group, which makes it capable of undergoing many chemical reactions. Its ability to form covalent bonds with other molecules makes it a crucial material in forming complex polymer structures. While it can be harmful if ingested or inhaled, proper handling and safety measures mitigate its risks.

Check Digit Verification of cas no

The CAS Registry Mumber 113538-80-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,3,5,3 and 8 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 113538-80:
(8*1)+(7*1)+(6*3)+(5*5)+(4*3)+(3*8)+(2*8)+(1*0)=110
110 % 10 = 0
So 113538-80-0 is a valid CAS Registry Number.
InChI:InChI=1S/C12H14O2/c1-2-10-3-5-11(6-4-10)7-13-8-12-9-14-12/h2-6,12H,1,7-9H2

113538-80-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-[(4-ethenylphenyl)methoxymethyl]oxirane

1.2 Other means of identification

Product number -
Other names 4-vinylbenxyl glycidyl ether

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:113538-80-0 SDS

113538-80-0Synthetic route

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

oxiranyl-methanol
556-52-5

oxiranyl-methanol

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 4h;86%
Stage #1: oxiranyl-methanol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere;
Stage #2: 4-Vinylbenzyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; for 4h; Inert atmosphere;
86%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h;85%
styrene
292638-84-7

styrene

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

Conditions
ConditionsYield
In toluene
1,4-bis(dimethylsilyl)benzene
2488-01-9

1,4-bis(dimethylsilyl)benzene

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

1,4-bis(dimethyl(4-((oxiran-2-ylmethoxy)methyl)phenethyl)silyl)benzene

1,4-bis(dimethyl(4-((oxiran-2-ylmethoxy)methyl)phenethyl)silyl)benzene

Conditions
ConditionsYield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene at 0 - 20℃; for 3.16667h; Inert atmosphere;90%
carbon dioxide
124-38-9

carbon dioxide

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

4-vinylbenzyl 2,5-dioxoran-3-ylmethyl ether

4-vinylbenzyl 2,5-dioxoran-3-ylmethyl ether

Conditions
ConditionsYield
With lithium bromide In N,N-dimethyl-formamide at 100℃; for 24h;81%
carbon disulfide
75-15-0

carbon disulfide

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

4-vinylbenzyl 1,3-oxathiolane-2-thione-5-ylmethyl ether
1414436-28-4

4-vinylbenzyl 1,3-oxathiolane-2-thione-5-ylmethyl ether

Conditions
ConditionsYield
With lithium bromide In tetrahydrofuran at 0 - 20℃;81%
2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

2-(2-(2-(2-(4-vinylbenzyloxy)ethoxy)ethoxy)ethoxy)ethanol
114689-61-1

2-(2-(2-(2-(4-vinylbenzyloxy)ethoxy)ethoxy)ethoxy)ethanol

polymer, Mw = 29168, Mn = 14023, Mw/Mn = 2.08; monomer(s): 4-vinyl benzyl tetraethyleneglycol ether; 4-vinyl benzyl glycidyl ether

polymer, Mw = 29168, Mn = 14023, Mw/Mn = 2.08; monomer(s): 4-vinyl benzyl tetraethyleneglycol ether; 4-vinyl benzyl glycidyl ether

Conditions
ConditionsYield
With 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile In chloroform at 45℃; for 48h;77%
4-butanolide
96-48-0

4-butanolide

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

C16H20O4
1470595-49-3

C16H20O4

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 4.5h;66%
hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

C18H24O4
1470595-51-7

C18H24O4

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 4.5h;63%
styrene
292638-84-7

styrene

1-(4-vinylbenzyl)-2-pyrrolidinone

1-(4-vinylbenzyl)-2-pyrrolidinone

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

tetraethylene glycol mono-2-phenyl-2-propenyl ether
515881-62-6

tetraethylene glycol mono-2-phenyl-2-propenyl ether

Reaxys ID: 11364530

Reaxys ID: 11364530

Conditions
ConditionsYield
2,2'-azobis(isobutyronitrile) In chloroform for 48h; Heating / reflux;61%
N-(p-tolyl)glycine
21911-69-3

N-(p-tolyl)glycine

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

NTG-VBE sodium salt

NTG-VBE sodium salt

Conditions
ConditionsYield
Stage #1: N-(p-tolyl)glycine With sodium hydroxide In tetrahydrofuran; water at 20℃; for 0.5h; pH=8.7;
Stage #2: 2-(4-vinyl-benzyloxymethyl)-oxirane In tetrahydrofuran; water at 20℃; for 48h;
57%
styrene
292638-84-7

styrene

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

2-(2-(2-(2-(4-vinylbenzyloxy)ethoxy)ethoxy)ethoxy)ethanol
114689-61-1

2-(2-(2-(2-(4-vinylbenzyloxy)ethoxy)ethoxy)ethoxy)ethanol

polymer, Mw 44664, Mw/Mn 1.80 by gel permeation chromatography; monomer(s): styrene; 4-vinylbenzyl glycidyl ether; 2-(2-(2-(2-(4-vinylbenzyloxy)ethoxy)ethoxy)ethoxy)ethanol

polymer, Mw 44664, Mw/Mn 1.80 by gel permeation chromatography; monomer(s): styrene; 4-vinylbenzyl glycidyl ether; 2-(2-(2-(2-(4-vinylbenzyloxy)ethoxy)ethoxy)ethoxy)ethanol

Conditions
ConditionsYield
With 2,2'-azobis(4-methoxy)-2,4-dimethylvaleronitrile In chloroform at 20℃; for 72h;56%
styrene
292638-84-7

styrene

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

tetraethylene glycol mono-2-phenyl-2-propenyl ether
515881-62-6

tetraethylene glycol mono-2-phenyl-2-propenyl ether

polymer, Mw = 69985, Mn = 12098; Monomer(s): styrene; 4-vinylbenzyl glycidyl ether; tetraethyleneglycol mono-2-phenyl-2-propenyl ether

polymer, Mw = 69985, Mn = 12098; Monomer(s): styrene; 4-vinylbenzyl glycidyl ether; tetraethyleneglycol mono-2-phenyl-2-propenyl ether

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In chloroform for 48h; Heating;53%
14-phenylpentadec-14-en-1-ol

14-phenylpentadec-14-en-1-ol

styrene
292638-84-7

styrene

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

Polymer, Mw: 23843, Mn: 18857, Mw/Mn: 1.26, ratio of monomers: 79/11/10; monomer(s): styrene; 4-vinylbenzyl glycidyl ether; 14-phenylpentadec-14-en-1-ol

Polymer, Mw: 23843, Mn: 18857, Mw/Mn: 1.26, ratio of monomers: 79/11/10; monomer(s): styrene; 4-vinylbenzyl glycidyl ether; 14-phenylpentadec-14-en-1-ol

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In chloroform for 24h; Heating;48%
styrene
292638-84-7

styrene

diphenyl(4-vinylphenyl)phosphine
40538-11-2

diphenyl(4-vinylphenyl)phosphine

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

tetraethylene glycol mono-2-phenyl-2-propenyl ether
515881-62-6

tetraethylene glycol mono-2-phenyl-2-propenyl ether

polymer, Mw = 49330, Mn = 25692, Mw/Mn = 1.92; monomer(s): styrene, 72 mol percent; 4-vinylbenzyl glycidyl ether, 12 mol percent; tetraethylene glycol mono-2-phenyl-2-propenyl ether, 5 mol percent; diphenyl(4-vinylphenyl)phosphine, 11 mol percent

polymer, Mw = 49330, Mn = 25692, Mw/Mn = 1.92; monomer(s): styrene, 72 mol percent; 4-vinylbenzyl glycidyl ether, 12 mol percent; tetraethylene glycol mono-2-phenyl-2-propenyl ether, 5 mol percent; diphenyl(4-vinylphenyl)phosphine, 11 mol percent

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 70℃; for 24h;
styrene
292638-84-7

styrene

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

tetraethylene glycol mono-2-phenyl-2-propenyl ether
515881-62-6

tetraethylene glycol mono-2-phenyl-2-propenyl ether

polymer, Mw 42798, Mn 14649 by GPC; monomer(s): styrene; 4-vinylbenzyl glycidyl ether; tetraethyleneglycol mono-2-phenyl-2-propenyl ether

polymer, Mw 42798, Mn 14649 by GPC; monomer(s): styrene; 4-vinylbenzyl glycidyl ether; tetraethyleneglycol mono-2-phenyl-2-propenyl ether

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In chloroform for 24h; Heating;37.0 g
N-(p-tolyl)glycine sodium salt

N-(p-tolyl)glycine sodium salt

2-(4-vinyl-benzyloxymethyl)-oxirane
113538-80-0

2-(4-vinyl-benzyloxymethyl)-oxirane

NTG-VBE sodium salt

NTG-VBE sodium salt

Conditions
ConditionsYield
With 2,4,6-tri-tert-butylphenoxol; sodium hydroxide In methanol; water pH=9;

113538-80-0Relevant articles and documents

N-heterocyclic carbene coordinated heterogeneous Pd nanoparticles as catalysts for suzuki-miyaura coupling

Min, Hyemin,Miyamura, Hiroyuki,Kobayashi, Shu

supporting information, p. 837 - 839 (2016/07/16)

Palladium nanoparticle (Pd NP) catalysts immobilized in a polymer with an N-heterocyclic carbene (NHC) moiety (PICBNHC-Pd) have been developed, wherein the NHC moiety plays dual roles as a crosslinker and a ligand to activate the Pd NPs. The presence of both Pd NPs and NHC was confirmed by STEM/EDS and SR-MAS NMR analyses, respectively. This PICB-NHC-Pd catalyst showed excellent activity in the Suzuki-Miyaura coupling reaction without leaching of Pd. Excellent results were obtained in gram-scale synthesis, and catalyst recovery/reuse experiments were completed without loss of catalyst activity.

Preparation of polymer incarcerated gold nanocluster catalysts (PI-Au) and their application to aerobic oxidation reactions of boronic acids, alcohols, and silyl enol ethers

Miyamura, Hiroyuki,Yasukawa, Tomohiro,Kobayashi, Shu

, p. 6039 - 6049 (2015/03/30)

Heterogeneous gold nanocluster catalysts immobilized by the method known as polymer incarceration were prepared. Polystyrene-derived polymers with epoxide and alcohol moieties, which could be cross-linked under heating conditions, were employed as supports for their preparation. Cationic gold salts were reduced in a solution of NaBH4 and the polymers. Poor solvents for the polymers were added, and the polymers were precipitated and encapsulated gold nanoclusters with weak but multiple interactions between a gold nanocluster surface and the π electrons of benzene rings. The polymer capsules were heated under neat conditions to afford heterogeneous gold nanocluster catalysts; namely, polymer-incarcerated gold nanoclusters. The catalysts thus prepared could be applied to the aerobic oxidation of phenyl boronic acids, alcohols, and silyl enol ethers. We found that the choice of polymers, good and poor solvents for the polymers, metal loadings, heating conditions for cross-linking, and final activation were all crucial for obtaining high-activity catalysts.

Copolymer-incarcerated nickel nanoparticles with N-heterocyclic carbene precursors as active cross-linking agents for Corriu-Kumada-Tamao reaction

Soule, Jean-Francois,Miyamura, Hiroyuki,Kobayashi, Shu

supporting information, p. 10602 - 10605 (2013/08/23)

We have developed heterogeneous polymer-incarcerated nickel nanoparticles (NPs), which catalyze cross-coupling reactions. The matrix structure of these catalysts incorporates both N-heterocyclic carbenes (NHCs) as ligands and Ni-NPs, thanks to a new design of cross-linking agents in polymer supports. These embedded NHCs were detected by field gradient swollen-resin magic angle spinning NMR analysis. They were successfully applied to Corriu-Kumada-Tamao reactions with a broad substrate scope including functional group tolerance, and the catalyst could be recovered and reused several times without loss of activity.

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