3,4-Dimethoxystyrene
Appearance
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Names | |
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Preferred IUPAC name
4-Ethenyl-1,2-dimethoxybenzene | |
Other names
1,2-Dimethoxy-4-vinylbenzene
4-Vinylveratrole 4-Vinyl-1,2-dimethoxybenzene | |
Identifiers | |
ChemSpider | |
ECHA InfoCard | 100.026.330 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C10H12O2 | |
Molar mass | 164.204 g·mol−1 |
Appearance | Yellowish oily liquid |
Odor | Sweet, floral |
Density | 1.109 g/cm3 |
Boiling point | 110–125 °C (230–257 °F; 383–398 K) |
Refractive index (nD)
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1.571 |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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flammable, toxic |
GHS labelling: | |
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Warning | |
H319 | |
P264, P280, P305+P351+P338, P337+P313 | |
Safety data sheet (SDS) | MSDS |
Related compounds | |
Related styrenes;
related aromatic compounds |
styrene, dimethoxybenzene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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3,4-Dimethoxystyrene (vinylveratrole) is an aromatic organic compound. It is a yellow oily liquid with a pleasant floral odor. Normally, it is supplied with 1-2% of the hydroquinone as an additive to prevent oxidation of the compound.
Occurrence
[edit]![]() | This section needs expansion. You can help by adding to it. (September 2015) |
3,4-Dimethoxystyrene is found in the essential oil of Brazilian propolis.[1] It is also found in cereal products and coffee products.[2]
Uses
[edit]- 3,4-Dimethoxystyrene is typically used in organic synthesis as a monomer in radical polymerization reactions due to the presence of the electron-deficient double bond.[3]
- 3,4-dimethoxystyrene can be deprotected using Lewis acid boron tribromide with almost 100% yield. The resulting compound 3,4-dihydroxystyrene is rapidly oxidized in air this is why 3,4-dimethoxystyrene is preferred as a stable precursor in organic synthesis.
- To the chemical community, it presents interest as an easily polymerizable precursor to polycatechols as it is less susceptible to oxidation in air.[4]
Pharmacology
[edit]Pharmacokinetics
[edit]Once ingested, 3,4-Dimethoxystyrene is found in the cytoplasm, and extracellularly.[2]
Related compounds
[edit]References
[edit]- ^ Kusumoto, Toshihide; Tomofumi, Miyamoto; Ryuichi, Higuchi; Shima, Doi; Hiroyuki, Sugimoto; Hideo, Yamada (2001). "Isolation and Structures of Two New Compounds from the Essential Oil of Brazilian Propolis" (PDF). Chem. Pharm. Bull. 49 (9): 1207–1209. doi:10.1248/cpb.49.1207. PMID 11558615. Retrieved 10 September 2015.
- ^ a b "Human Metabolome Database: Showing metabocard for 1,2-Dimethoxy-4-vinylbenzene (HMDB0040359)". hmdb.ca. Retrieved 2024-02-28.
- ^ Rooney, J.M. (1983). "Cationic polymerization of 3,4-dimethoxystyrene by trityl hexachloroantimonate". Polymer Bulletin. 10 (9–10): 414–418. doi:10.1007/bf00262183. S2CID 95803836.
- ^ Daly, William H.; Moulay, Saad (2007). "Synthesis of poly (vinylcatechols)". Journal of Polymer Science: Polymer Symposia. 74: 227–242. doi:10.1002/polc.5070740120. S2CID 93597941.