3,4-Dimethoxystyrene
 | |
| Names | |
|---|---|
| Preferred IUPAC name
1,2-Dimethoxy-4-vinylbenzene | |
| Other names
4-Vinylveratrole; 4-Ethenyl-1,2-dimethoxybenzene; 4-Vinyl-1,2-dimethoxybenzene | |
| Identifiers | |
6380-23-0  | |
| ChemSpider | 55329 |
| ECHA InfoCard | 100.026.330 |
| PubChem | 24849444 |
| UNII | 50PLH4M73W |
| |
| Properties | |
| C10H12O2 | |
| Molar mass | 164.20 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 | R40 R36 R43 R60 |
| S-phrases | 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 | |
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
3,4-Dimethoxystyrene is found in the essential oil of Brazilian propolis.[1]
Uses
- 3,4-Dimethoxystyrene is typically used in organic synthesis as a monomer in radical polymerization reactions due to the presence of the electron-defficient 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. 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, H. W.; Moulay, S. (1986). "Synthesis of poly(vinylcatechols)". S.J. Polym.Sci. 242 (74): 227–242.
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