4-Bromostyrene
Synonym(s):p -Bromostyrene;1-(4-Bromophenyl)ethylene;1-Bromo-4-ethenylbenzene;1-Bromo-4-vinylbenzene;4-Vinyl-1-bromobenzene
- CAS NO.:2039-82-9
- Empirical Formula: C8H7Br
- Molecular Weight: 183.05
- MDL number: MFCD00000110
- EINECS: 218-022-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-01 18:09:03
What is 4-Bromostyrene?
Chemical properties
clear slightly yellow to yellow liquid
The Uses of 4-Bromostyrene
4-Bromostyrene is widely utilized in the synthesis of nitroolefins by alkene cross-metathesis. It plays an important role in the Heck reaction to the synthesis of poly(1,4-phenylenevinylene). It is employed in the structure activity relationships (SAR) study of the chemical and biochemical properties of the vinyl group of styrene. It is also used to investigate the photochemical growth of Br-terminated self-assembled monolayers. It is also involved in the synthesis of silsesquioxanes.
What are the applications of Application
4-Bromostyrene is a compound useful for synthesis of nitroolefins via alkene cross-metathesis
General Description
4-Bromostyrene is a para-halogenated styrene derivative. The proton spectra of 4-bromostyrene exhibits dipolar couplings consistent with planar ground state structures, only if the torsional motion of lowest frequency occurs at about 80cm-1. It undergoes Heck reaction with 2-bromo-6-methoxynaphthalene in the presence of sodium acetate and Hermann′s catalyst in N,N-dimethylacetamide to afford diarylethene.
Purification Methods
It polymerises above 75o in the presence of benzoyl peroxide. To purify, if it has not gone to a solid resin, dissolve it in Et2O, dry (MgSO4) and add ca 0.1g of 4-tertbutylcatechol (polymerisation inhibitor) per 100g of bromostyrene. Filter, evaporate this under reduced pressure (use as high a vacuum as possible) and distil the residue. Store it in dark bottles in the presence of the inhibitor (at above concentration). [Overberger & Saunders Org Synth Coll Vol III 204 1955, Beilstein 5 IV 1349.]
Properties of 4-Bromostyrene
Melting point: | 4.5 °C |
Boiling point: | 89 °C16 mm Hg(lit.) |
Density | 1.40 g/mL at 20 °C |
refractive index | n |
Flash point: | 168 °F |
storage temp. | -20°C |
solubility | Miscible with ethanol, ether and benzene. |
form | Liquid |
color | light greenish-yellow |
BRN | 1634204 |
CAS DataBase Reference | 2039-82-9(CAS DataBase Reference) |
NIST Chemistry Reference | 4-BrC6H4CH=CH2(2039-82-9) |
Safety information for 4-Bromostyrene
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention. |
Computed Descriptors for 4-Bromostyrene
InChIKey | WGGLDBIZIQMEGH-UHFFFAOYSA-N |
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