3,4-Dimethoxystyrene

3,4-Dimethoxystyrene
Names
	Preferred IUPAC name 4-Ethenyl-1,2-dimethoxybenzene
	Other names 1,2-Dimethoxy-4-vinylbenzene; 4-Vinylveratrole; 4-Vinyl-1,2-dimethoxybenzene
Identifiers
CAS Number	6380-23-0 ;
ChemSpider	55329 ;
ECHA InfoCard	100.026.330
PubChem CID	24849444;
UNII	50PLH4M73W ;
	InChI InChI=11/C10H12O2/c1-4-8-5-6-9(11-2)10(7-8)12-3/h4-7H,1H2,2-3H ;
Properties
Chemical formula	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R-phrases (outdated)	R40 R36 R43 R60
S-phrases (outdated)	S26 S36/37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

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-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. 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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[1] 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.

[2] Rooney, J.M. (1983). "Cationic polymerization of 3,4-dimethoxystyrene by trityl hexachloroantimonate". Polymer bulletin. 10 (9–10): 414–418. doi:10.1007/bf00262183.

[3] Daly, H. W.; Moulay, S. (1986). "Synthesis of poly(vinylcatechols)". S.J. Polym.Sci. 242 (74): 227–242.