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.

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 Y
ChemSpider	55329 Y
ECHA InfoCard	100.026.330
EC Number	228-962-9
PubChem CID	61400
UNII	50PLH4M73W Y
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 Y
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). N verify (what is YN ?) Infobox references

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

• 3,4-Dihydroxystyrene
• Veratrole