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 | |
|---|---|
| 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| R-phrases (outdated) | R40 R36 R43 R60 |
| S-phrases (outdated) | S26 S36/37 |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). | |
 verify (what is  ?) | |
| 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
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. PMID 11558615. 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. 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.
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