2,6-Dimethoxy-4-vinylphenol

Base Information

• Chemical Name: 2,6-Dimethoxy-4-vinylphenol
• CAS No.: 28343-22-8
• Molecular Formula: C10H12 O3
• Molecular Weight: 180.203
• Hs Code.: 2909500000
• European Community (EC) Number: 848-947-6
• UNII: ZB5OK5EX8B
• DSSTox Substance ID: DTXSID30865427
• Nikkaji Number: J588.629E
• Wikipedia: Canolol
• Wikidata: Q15634956
• Mol file: 28343-22-8.mol

Synonyms:4-vinyl-2,6-dimethoxyphenol;canolol

Chemical Property of 2,6-Dimethoxy-4-vinylphenol

Chemical Property:

• Vapor Pressure: 0.00163mmHg at 25°C
• Boiling Point: 285.4°Cat760mmHg
• PKA: 10.02±0.36(Predicted)
• Flash Point: 126.4°C
• PSA: 38.69000
• Density: 1.113g/cm³
• LogP: 2.05240
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 180.078644241
• Heavy Atom Count: 13
• Complexity: 156

Purity/Quality:

99% ^*data from raw suppliers

2,6-DIMETHOXY-4-VINYLPHENOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C=C
• General Description: Phenol, 4-ethenyl-2,6-dimethoxy- (also known as canolol or vinylsyringol) is a bio-based phenolic compound that has been investigated as a precursor for synthesizing sustainable epoxy monomers. When dimerized and epoxidized, derivatives of Phenol, 4-ethenyl-2,6-dimethoxy- exhibit moderate binding affinity to the estrogen receptor α (ERα), though significantly lower than bisphenol A (BPA), suggesting a reduced risk of endocrine disruption. This makes it a promising candidate for safer, environmentally friendly alternatives to conventional epoxy resins like DGEBA.

Technology Process of 2,6-Dimethoxy-4-vinylphenol

There total 17 articles about 2,6-Dimethoxy-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: 95.0%

ethyltriphenylphosphonium bromide (1530-32-1) + syringic aldehyde (134-96-3) → canolol (28343-22-8,31872-14-7)

Guidance literature:

ethyl(trisphenyl)phosphonium bromide; With potassium-t-butoxide; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere; Sealed tube;

syringic aldehyde; In tetrahydrofuran; at 0 - 20 ℃; for 40h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.2c00566

Reference yield: 94.0%

sinapinic acid (530-59-6,7362-37-0) → canolol (28343-22-8,31872-14-7)

Guidance literature:

With Cocos nucifera juice; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.molcatb.2012.06.004

Reference yield: 90.0%

1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanol (33900-62-8) → canolol (28343-22-8,31872-14-7)

Guidance literature:

With MoO₂Cl₂(DMSO)2; dimethyl sulfoxide; for 0.166667h; Microwave irradiation;

DOI:10.1002/cssc.201800598

upstream raw materials:

malonic acid

syringic aldehyde

sinapinic acid

C₄H₁₁N*C₁₁H₁₂O₅

Downstream raw materials:

(E)-4'-fluoro-4-hydroxy-3,3',5,5'-tetramethoxystilbene

(E)-4-hydroxy-2',3,5,5'-tetramethoxystilbene

(E)-3,5-dimethoxy-3',4,5'-trihydroxystilbene

(E)-3,5-dimethoxy-4,2',5'-trihydroxystilbene

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.