2-Methoxy-4-vinylphenol

Base Information

• Chemical Name: 2-Methoxy-4-vinylphenol
• CAS No.: 7786-61-0
• Molecular Formula: C9H10O2
• Molecular Weight: 150.177
• Hs Code.: 29095000
• European Community (EC) Number: 232-101-2
• UNII: DA069CTH0O
• DSSTox Substance ID: DTXSID7052529
• Nikkaji Number: J134.783G
• Wikipedia: 2-Methoxy-4-vinylphenol
• Wikidata: Q4596898
• Metabolomics Workbench ID: 42489
• ChEMBL ID: CHEMBL1232595
• Mol file: 7786-61-0.mol

Synonyms:4-hydroxy-3-methoxystyrene;4-vinylguaiacol

Chemical Property of 2-Methoxy-4-vinylphenol

Chemical Property:

• Appearance/Colour: Colorless to slightly yellow liquid
• Vapor Pressure: 0.0188mmHg at 25°C
• Melting Point: 25-29 °C
• Refractive Index: n20/D 1.582(lit.)
• Boiling Point: 244.958 °C at 760 mmHg
• PKA: 10.00±0.31(Predicted)
• Flash Point: 111.343 °C
• PSA: 29.46000
• Density: 1.09 g/cm³
• LogP: 2.04380
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slig
• Water Solubility.: Miscible with water.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 150.068079557
• Heavy Atom Count: 11
• Complexity: 134

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

p-Vinylguaiacol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C=C)O
• Uses: p-Vinylguaiacol is an aromatic substance and one of the compounds responsible for the natural aroma of buckwheat. It is also one of the major pyrolytic products of (E)-N-[(4-hydroxy-3-methoxy)-phenethyl]-3-[(3-methoxy-4-O-β-D-glucopyranosyloxy) phenyl] acrylamide; a new gycloside in tobacco.

Technology Process of 2-Methoxy-4-vinylphenol

There total 44 articles about 2-Methoxy-4-vinylphenol 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%

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) → 3-methoxy-4-hydroxystyrene (7786-61-0,31853-85-7)

Guidance literature:

With phosphate buffer; Catharanthus roseus; at 25 ℃; for 72h; pH=6.0;

DOI:10.1248/cpb.49.639

Reference yield: 98.0%

3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) → 3-methoxy-4-hydroxystyrene (7786-61-0,31853-85-7)

Guidance literature:

With ferulic acid decarboxylase from Enterobacter sp; In aq. phosphate buffer; at 30 ℃; for 19h; pH=7; Sealed tube; Enzymatic reaction;

DOI:10.1021/acs.orglett.8b02058

Reference yield: 95.0%

4-acetoxy-3-methoxyvinylbenzene (46316-15-8) → 3-methoxy-4-hydroxystyrene (7786-61-0,31853-85-7)

Guidance literature:

With cucumber juice; at 30 - 35 ℃; for 6h; Inert atmosphere; Green chemistry;

DOI:10.1039/c6ra01760f

upstream raw materials:

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

4,4-(ethane-1,1-diyl)bis(2-methoxyphenol)

methyl magnesium iodide

diethyl ether

Downstream raw materials:

trans-piceatannol

(E)-3,3',5,5'-tetrahydroxystilbene

(E)-3,3'-dimethoxy-4,4'-dihydroxystilbene

4-acetoxy-3-methoxyvinylbenzene

Refernces

Synthesis of bio-based epoxy monomers from natural allyl- and vinyl phenols and the estimation of their affinity to the estrogen receptor α by molecular docking

10.1039/c6nj00782a

This study investigates the creation of sustainable epoxy monomers as alternatives to the diglycidyl ether of bisphenol A (DGEBA). The researchers synthesized diepoxydized diphenyls from eugenol, 4-vinyl guaiacol, and canolol through glycidylation with epichlorohydrin followed by cross metathesis (CM) dimerization using the Grubbs II catalyst. The synthesized products and their hydrolysed forms were then assessed for their potential endocrine-disrupting activity by estimating their binding affinity to the estrogen receptor a (ERa) using molecular docking. The study found that the epoxy forms had a moderate affinity to the antagonistic conformation of ERa, six to forty times lower than bisphenol A (BPA), while their hydrolysed forms exhibited relatively weak affinity in both agonistic and antagonistic conformations. This suggests that the synthesized bio-based epoxy monomers could serve as safer alternatives to DGEBA, with reduced potential for endocrine disruption.