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4-Hydroxystyrene
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Name

4-Hydroxystyrene

 EINECS 220-103-6
CAS No. 2628-17-3 Density 1.055 g/cm3
PSA 20.23000 LogP 2.03520
Solubility Slightly miscible with water. Melting Point 73 °C
Formula C8H8O Boiling Point 206.2 °C at 760 mmHg
Molecular Weight 120.151 Flash Point 92.3 °C
Transport Information N/A Appearance N/A
Safety 26-39 Risk Codes 22-41
Molecular Structure Molecular Structure of 2628-17-3 (4-Hydroxystyrene) Hazard Symbols HarmfulXn
Synonyms

Phenol,p-vinyl- (6CI,7CI,8CI);4-Ethenylphenol;4-Hydroxystyrene;4-Vinylphenol;p-Hydroxystyrene;p-Vinylphenol;

Article Data 155

4-Hydroxystyrene Synthetic route

7400-08-0

para-coumaric acid

2628-17-3

4-Vinylphenol

Conditions
ConditionsYield
With sodium hydroxide at 160℃; for 5h;99.3%
With cucumber juice at 30 - 35℃; for 24h; Inert atmosphere; Green chemistry;94%
With aluminum oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydroquinone In methanol for 0.333333h; microwave irradiation;85%
1779-49-3

Methyltriphenylphosphonium bromide

123-08-0

4-hydroxy-benzaldehyde

2628-17-3

4-Vinylphenol

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: 4-hydroxy-benzaldehyde In tetrahydrofuran at 20℃; for 1h; Wittig Olefination;		98%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate; sodium hydride In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: 4-hydroxy-benzaldehyde In tetrahydrofuran at 20℃; for 19h;		95%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Schlenk technique;
Stage #2: 4-hydroxy-benzaldehyde In tetrahydrofuran at 0 - 20℃;		89%
141-82-2

malonic acid

123-08-0

4-hydroxy-benzaldehyde

2628-17-3

4-Vinylphenol

Conditions
ConditionsYield
With ethylenediamine In N,N-dimethyl-formamide at 150℃; for 6h; Reagent/catalyst; Solvent; Large scale;98%
With piperidine; 4-methoxy-phenol In hexane; 2-methoxy-ethanol at 65℃; for 24h; Reagent/catalyst; Temperature; Solvent;87.4%
With piperidine In pyridine at 115℃; for 4h; Knoevenagel condensation reaction;86%
7400-08-0

p-Coumaric Acid

2628-17-3

4-Vinylphenol

Conditions
ConditionsYield
With 4-methoxy-phenol In water; N,N-dimethyl-formamide at 150℃; for 4h; Solvent;97%
With 1-methyl-1H-imidazole; sodium hydrogencarbonate for 0.333333h; Heating; microwave irradiation;94%
With bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate; potassium acetate In DMF (N,N-dimethyl-formamide) at 150℃; for 1.5h; Product distribution / selectivity;94%
19704-86-0

N,N-dimethyl-L-tyrosine N-oxide

2628-17-3

4-Vinylphenol

Conditions
ConditionsYield
potassium acetate In N,N-dimethyl acetamide at 123℃; for 2.4h; Product distribution / selectivity;97%
2628-16-2

p-acetoxystyrene

2628-17-3

4-Vinylphenol

Conditions
ConditionsYield
With ethanol; sodium hydroxide at 20℃; for 4h; Inert atmosphere;96%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 4h; Cooling with ice; Inert atmosphere; Schlenk technique;96%
With ethanol; sodium hydroxide at 20℃; for 4h; Inert atmosphere;96%
19704-86-0

N,N-dimethyl-L-tyrosine N-oxide

A

7400-08-0

p-Coumaric Acid

B

2628-17-3

4-Vinylphenol

Conditions
ConditionsYield
potassium acetate In N,N-dimethyl acetamide at 123℃; for 2.5h; Product distribution / selectivity;A 4%
B 96%
2156-04-9

4-Vinylphenylboronic acid

2628-17-3

4-Vinylphenol

Conditions
ConditionsYield
With N,N-dimethyl-p-toluidine N-oxide In dichloromethane at 20℃; for 0.0166667h;95%
With urea hydrogen peroxide adduct In acetonitrile at 27 - 29℃; for 0.75h; Temperature; Solvent; Green chemistry; chemoselective reaction;95%
With copper(II) sulfate hydrate; potassium hydroxide In water at 20℃; for 24h;91%
123-08-0

4-hydroxy-benzaldehyde

2628-17-3

4-Vinylphenol

Conditions
ConditionsYield
With potassium tert-butylate; Methyltriphenylphosphonium bromide In tetrahydrofuran at 0 - 20℃; for 16h;95%
Multi-step reaction with 2 steps
1: pyridine; glycine / 3 h / 80 °C / Sealed tube
2: pyridine; glycine / 8 h / 140 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / dichloromethane / 2 h / 20 °C
2: potassium carbonate / tetrahydrofuran / 24 h / 70 °C
3: sodium hydroxide; methanol / 0.5 h / 20 °C
View Scheme
106-41-2

4-bromo-phenol

1826-67-1

vinyl magnesium bromide

2628-17-3

4-Vinylphenol

Conditions
ConditionsYield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran -78 deg C, 10 min, reflux, 0.5 h;91%

4-Hydroxystyrene Chemical Properties

Molecular Formula: C8H8O
Molar mass: 120.15 g/mol
EINECS: 220-103-6
Density: 1.055 g/cm3
Flash Point: 92.3 °C
Index of Refraction: 1.602
Boiling Point: 206.2 °C at 760 mmHg
Vapour Pressure: 0.168 mmHg at 25°C
Melting point: 73 ºC
Sensitive: Hygroscopic
Product categories of 4-Vinylphenol (2628-17-3): Aromatic Phenols
Structure of 4-Vinylphenol (2628-17-3):
           
XLogP3-AA: 2.4
H-Bond Donor: 1
H-Bond Acceptor: 1
Systematic Name: 4-Vinylphenol 
SMILES: Oc1ccc(\C=C)cc1 
InChI: InChI=1/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2 
InChIKey: FUGYGGDSWSUORM-UHFFFAOYAQ 
Std. InChI: InChI=1S/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2 
Std. InChIKey: FUGYGGDSWSUORM-UHFFFAOYSA-N

4-Hydroxystyrene Toxicity Data With Reference

1.    

eye-rbt 100 mg SEV

     EPASR*    United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401M St., S.W., Washington, DC 20460) History Unknown 8EHQ-1285-0579S .
2.    

skn-rbt LDLo:200 mg/kg

     EPASR*    United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401M St., S.W., Washington, DC 20460) History Unknown 8EHQ-1285-0579S .
3.    

ocu-rbt LDLo:50 mg/kg

     EPASR*    United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401M St., S.W., Washington, DC 20460) History Unknown 8EHQ-1285-0579S .

4-Hydroxystyrene Safety Profile

Poison by skin and eye contact. Severe eye irritant. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: Xn
Risk Statements:
22:  Harmful if swallowed 
41:  Risk of serious damage to eyes
Safety Statements:
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
39:  Wear eye/face protection

4-Hydroxystyrene Specification

 4-Vinylphenol (2628-17-3) also can be called Poly(4-vinylphenol) ; 4-Hydroxystyrene ; 4-Ethenylphenol ; Poly(p-vinylphenol) and phenol, 4-ethenyl- .

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