Allyl phenyl ether

Base Information

• Chemical Name: Allyl phenyl ether
• CAS No.: 1746-13-0
• Molecular Formula: C9H10O
• Molecular Weight: 134.178
• Hs Code.: 29093090
• European Community (EC) Number: 217-125-3
• NSC Number: 4746
• UNII: 26S07OSX4O
• DSSTox Substance ID: DTXSID6061943
• Nikkaji Number: J7.765H
• Wikipedia: Allyl_phenyl_ether
• Wikidata: Q4733437
• Mol file: 1746-13-0.mol

Synonyms:phenyl 2-propen-1-yl ether;phenyl allyl ether

Chemical Property of Allyl phenyl ether

Chemical Property:

• Appearance/Colour: Clear colourless to very slightly yellow liquid
• Vapor Pressure: 0.682mmHg at 25°C
• Melting Point: 90 °C(Solv: water (7732-18-5))
• Refractive Index: n20/D 1.522(lit.)
• Boiling Point: 192.4 °C at 760 mmHg
• Flash Point: 62.8 °C
• PSA: 9.23000
• Density: 0.947 g/cm³
• LogP: 2.25140
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility.: insoluble
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 134.073164938
• Heavy Atom Count: 10
• Complexity: 92.9

Purity/Quality:

99% ^*data from raw suppliers

Allyl Phenyl Ether ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCOC1=CC=CC=C1
• Uses: Allyl phenyl ether is an pharmaceutical and OLED intermediate.

Technology Process of Allyl phenyl ether

There total 129 articles about Allyl phenyl ether which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-phenoxymethylepisulfide (3221-14-5) → allyl phenyl ether (1746-13-0)

Guidance literature:

With hydrogen sulfide; triphenylphosphine; methyltrioxorhenium(VII); In [D₃]acetonitrile; for 6h; Ambient temperature;

DOI:10.1039/a901708i

Reference yield: 98.0%

allyl bromide (106-95-6) + phenol (108-95-2,27073-41-2) → allyl phenyl ether (1746-13-0)

Guidance literature:

With potassium carbonate; sodium iodide; In acetone; for 15h; Heating;

Reference yield: 95.0%

allyl bromide (106-95-6) + phenylboronic acid (98-80-6) → allyl phenyl ether (1746-13-0)

Guidance literature:

phenylboronic acid; With dihydrogen peroxide; cholin hydroxide; In water; at 20 ℃; for 1h; Green chemistry;

allyl bromide; In water; at 20 ℃; for 2h; Green chemistry;

DOI:10.1016/j.tetlet.2020.152197

upstream raw materials:

allyl benzenesulfonate

sodium phenoxide

1-(3-iodopropoxy)benzene

allyl tosylate

Downstream raw materials:

3,3-dinitro-2-(1-nitromethyl-2-phenoxy-ethoxy)-5-phenoxymethyl-isoxazolidine

1-allyloxy-4-chlorobenzene

allylcyclopentane

1-(3-phenoxy-3-propenyl)cyclohexanol

Refernces

Dihydrobenzofuran production from catalytic tandem Claisen rearrangement-intramolecular hydroaryloxylation of allyl phenyl ethers in subcritical water

10.1039/c4ra04689g

The research explores a novel method for synthesizing dihydrobenzofurans, which are key structural components in many biologically active compounds. The study investigates the tandem Claisen rearrangement and intramolecular hydroaryloxylation of allyl phenyl ethers in subcritical water (SBW) using various zeolite catalysts (SBA-15, TS-1, and HZSM-5). The experiments were conducted at temperatures ranging from 200 to 320 °C, with HZSM-5 demonstrating the highest catalytic activity. The study found that temperature and catalyst type significantly influenced product yields, with 2-methyl-2,3-dihydrobenzofuran being the primary product. The optimal reaction conditions were identified as 260 °C with an APE–water molar ratio of 1:40, yielding 65% of the desired product. The HZSM-5 catalyst showed high selectivity and recyclability, maintaining its activity over multiple uses. The study also tested various allyl phenyl ether derivatives, achieving high yields (83–95%) of corresponding dihydrobenzofurans.