2-Vinylanisole

Base Information

• Chemical Name: 2-Vinylanisole
• CAS No.: 612-15-7
• Molecular Formula: C9H10O
• Molecular Weight: 134.178
• Hs Code.: 2909309090
• European Community (EC) Number: 210-294-4
• UNII: G0I9DYE185
• DSSTox Substance ID: DTXSID9060605
• Nikkaji Number: J43.391H
• Wikidata: Q27278445
• Metabolomics Workbench ID: 47353
• Mol file: 612-15-7.mol

Synonyms:2-Vinylanisole;2-Methoxystyrene;612-15-7;1-Methoxy-2-vinylbenzene;1-Ethenyl-2-methoxybenzene;o-Vinylanisole;BENZENE, 1-ETHENYL-2-METHOXY-;o-methoxystyrene;Methoxystyrene, o-;Anisole, o-vinyl-;2-?METHOXYSTYRENE;FEMA No. 3248;UNII-G0I9DYE185;G0I9DYE185;EINECS 210-294-4;2-Vinylanisole, 98%;2-vinyl anisole;2-vinyl-anisole;O-Vinyl-Anisole;ortho-vinyl anisole;O-VINYL ANISOLE;2-ethenyl methoxy benzene;SCHEMBL14909;1-Ethenyl-2-methoxy-Benzene;UPCMLD00WCRH4-146;O-VINYL ANISOLE [FHFI];DTXSID9060605;SCHEMBL13341238;CHEBI:178625;1-Ethenyl-2-methoxybenzene, 9CI;MFCD00080566;UPCMLD00WCRH4-146:002;UPCMLD00WCRH4-146:003;AKOS009827328;AS-81351;FEMA NO. 3248 (GRAS DELISTED);CS-0144527;FT-0702137;W15267;Q27278445

Chemical Property of 2-Vinylanisole

Chemical Property:

• Appearance/Colour: white or yellow dust
• Vapor Pressure: 0.514mmHg at 25°C
• Melting Point: 29°C
• Refractive Index: n20/D 1.5540(lit.)
• Boiling Point: 198.1 °C at 760 mmHg
• Flash Point: 70.6 °C
• PSA: 9.23000
• Density: 0.962 g/cm³
• LogP: 2.33820
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 134.073164938
• Heavy Atom Count: 10
• Complexity: 109

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Vinylanisole 98% ^*data from reagent suppliers

Safty Information:

• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=CC=C1C=C

Technology Process of 2-Vinylanisole

There total 65 articles about 2-Vinylanisole 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: 92.0%

Methyltriphenylphosphonium bromide (1779-49-3) + ortho-anisaldehyde (135-02-4) → o-methoxystyrene (612-15-7)

Guidance literature:

Methyltriphenylphosphonium bromide; With t-PeOK; In tetrahydrofuran; toluene; at 20 ℃; for 0.25h; Inert atmosphere;

ortho-anisaldehyde; In tetrahydrofuran; toluene; at 20 ℃; for 1.33333h; Cooling with ice;

DOI:10.1002/chem.201501959

Reference yield: 87.0%

2-bromoanisole (578-57-4) + 2,4,6-trivinylcyclotriboroxane*pyridine complex → o-methoxystyrene (612-15-7)

Guidance literature:

With potassium phosphate; bis(di-tert-butyl(2-butenyl)phosphine)dichloropalladium; In 1,4-dioxane; water; at 80 ℃; for 6h; Reagent/catalyst; Inert atmosphere;

Reference yield: 87.0%

2-allylanisole (3698-28-0) + ethene (74-85-1) → o-methoxystyrene (612-15-7)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; di-μ-bromobis-(tritert-butylphosphine)dipalladium(I); In tetrahydrofuran; at 60 ℃; for 16h; under 7500.75 Torr; Autoclave;

DOI:10.1002/chem.201301336

upstream raw materials:

pyridine

1-chloro-1-(2-methoxyphenyl)ethane

1-(2-methoxyphenyl)ethanol

2-methoxyphenethyl alcohol

Downstream raw materials:

2-ethylanisole

(Z)-1-Bromo-2-(o-methoxyphenyl)ethylene

2-Methoxy-zimtsaeure-amid

4-(2-methoxyphenyl)azetidin-2-one

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.