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
EC Number	228-962-9;
PubChem CID	61400;
UNII	50PLH4M73W ;
CompTox Dashboard (EPA)	DTXSID6064296 ;
	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	164.204 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
	Occupational safety and health (OHS/OSH):
Main hazards	flammable, toxic
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	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). 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] It is also found in cereal products and coffee products.^[2]

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.^[3] This is similar to the parent compound styrene, which can be polymerized into polystyrene.
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, which is why 3,4-dimethoxystyrene is preferred as a stable precursor in organic synthesis.
It is an easily polymerizable precursor to polycatechols as it is less susceptible to oxidation in air than other precursors.^[4]

Pharmacology

Pharmacokinetics

Once ingested, 3,4-Dimethoxystyrene is found in the cytoplasm, and extracellularly.^[2]

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.
^ ^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.

[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. PMID 11558615. Retrieved 10 September 2015.

[:0-2] "Human Metabolome Database: Showing metabocard for 1,2-Dimethoxy-4-vinylbenzene (HMDB0040359)". hmdb.ca. Retrieved 2024-02-28.

[3] 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.

[4] 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.

[1]

[2]

[3]

[4]