3,4-Dimethoxystyrene
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.
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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 |
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) |
1.571 |
Hazards | |
Main hazards | flammable, toxic |
Safety data sheet | MSDS |
R-phrases (outdated) | R40 R36 R43 R60 |
S-phrases (outdated) | S26 S36/37 |
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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Infobox references | |
Uses
- 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.[2]
- 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.[3]
Related compounds
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References
- 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. Retrieved 10 September 2015.
- Rooney, J.M. (1983). "Cationic polymerization of 3,4-dimethoxystyrene by trityl hexachloroantimonate". Polymer Bulletin. 10 (9–10): 414–418. doi:10.1007/bf00262183.
- Daly, William H.; Moulay, Saad (2007). "Synthesis of poly (vinylcatechols)". Journal of Polymer Science: Polymer Symposia. 74: 227–242. doi:10.1002/polc.5070740120.
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