4-Methoxystyrene

Base Information

• Chemical Name: 4-Methoxystyrene
• CAS No.: 637-69-4
• Molecular Formula: C9H10O
• Molecular Weight: 134.178
• Hs Code.: 29093090
• European Community (EC) Number: 211-298-9
• NSC Number: 408326,42171
• UNII: 2ISH8T4A6E
• DSSTox Substance ID: DTXSID7073222
• Nikkaji Number: J43.389F
• Wikipedia: 4-Vinylanisole
• Wikidata: Q27254796
• Mol file: 637-69-4.mol

Synonyms:Anisole,p-vinyl- (6CI,8CI);(4-Methoxyphenyl)ethene;(4-Methoxyphenyl)ethylene;1-Ethenyl-4-methoxybenzene;1-Methoxy-4-vinylbenzene;4-Methoxystyrene;4-Methoxyvinylbenzene;NSC 408326;NSC 42171;p-Anisylethylene;p-Methoxystyrene;p-Vinylanisole;

Chemical Property of 4-Methoxystyrene

Chemical Property:

• Appearance/Colour: Clear colourless liquid
• Melting Point: 3.3ºC
• Refractive Index: n20/D 1.562
• Boiling Point: 220.708 °C at 760 mmHg
• Flash Point: 77.715 °C
• PSA: 9.23000
• Density: 0.963 g/cm³
• LogP: 2.33820
• Storage Temp.: 2-8°C
• Solubility.: Slightly miscible with methanol.
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 134.073164938
• Heavy Atom Count: 10
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

4-Methoxystyrene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Ethers, Other
• Canonical SMILES: COC1=CC=C(C=C1)C=C
• General Description: 4-Methoxystyrene (also known as p-Methoxystyrene) is a chemical compound involved in photohydration reactions, where it undergoes intramolecular proton transfer. The study highlights its reactivity in comparison to other substituted styrenes, particularly noting the influence of substituents on reaction mechanisms and regioselectivity. However, the abstract does not provide specific experimental data or conclusions solely about 4-Methoxystyrene, focusing instead on broader trends among the tested compounds. Thus, no definitive conclusions about 4-Methoxystyrene itself can be drawn from this abstract.

Technology Process of 4-Methoxystyrene

There total 311 articles about 4-Methoxystyrene 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: 99.0%

4-methoxyphenylacetylen (768-60-5) → 4-Methoxystyrene (637-69-4,24936-44-5)

Guidance literature:

With hydrogen; 3-azapentane-1,5-diamine; In methanol; at 25 ℃; for 6h;

DOI:10.1002/adsc.201100936

Reference yield: 99.0%

1-bromo-4-methoxy-benzene (104-92-7) + tri-n-butyl(vinyl)tin (7486-35-3) → 4-Methoxystyrene (637-69-4,24936-44-5)

Guidance literature:

With cesium fluoride; palladium diacetate; In 1,4-dioxane; at 100 ℃; for 3h;

DOI:10.1055/s-2004-836023

Reference yield: 93.0%

tetravinylsilane (1112-55-6) + para-iodoanisole (696-62-8) → 4-Methoxystyrene (637-69-4,24936-44-5)

Guidance literature:

With palladium(II) acetylacetonate; potassium fluoride; In N,N-dimethyl-formamide; at 130 ℃; for 3h; under 1500.15 Torr; Reagent/catalyst; Time; Inert atmosphere;

DOI:10.1016/j.jcat.2013.02.019

upstream raw materials:

methyl magnesium iodide

4-methoxymandelonitrile

diethyl ether

4-methoxy-mandelimidic acid ethyl ester

Downstream raw materials:

3-(morpholin-1-yl)-1-(4-methoxyphenyl)propan-1-ol

2-(4-methoxyphenyl)acetaldehyde dimethyl acetal

1-acetoxy-1-methoxy-2-(4-methoxy-phenyl)-ethane

1-acetoxy-2-p-methoxyphenylethyl acetate

Refernces

Intramolecular Proton Transfer in Photohydration Reactions

10.1021/ja00280a028

The study investigates the photohydration reactions of various o-hydroxy- and o-methoxystyrenes (compounds 1-10), as well as p-hydroxy- (11) and p-methoxystyrene (12) through intramolecular proton transfer. The researchers found that non-nitro-substituted o-hydroxystyrenes undergo Markovnikov addition of water to form 1-arylethanols, while nitro-substituted o-hydroxystyrenes show no pH dependence in product quantum yield and produce 2-(2-hydroxyphenyl)ethanols via anti-Markovnikov addition. The study also explores the effects of different substituents on the reaction efficiency, acid catalysis, and regioselectivity. The absolute quantum yields for compounds 1 and 9 at pH 2 were determined to be 0.19 and 0.41, respectively. The researchers used various techniques, including UV spectroscopy, fluorescence quenching, and triplet sensitization and quenching experiments, to analyze the reaction mechanisms and rate constants. The results provide insights into the structural requirements and effective molarities necessary for efficient intramolecular proton transfer in photohydration reactions.