Conditions | Yield |
---|---|
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% |
Methyltriphenylphosphonium bromide
4-hydroxy-benzaldehyde
4-Vinylphenol
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
N,N-dimethyl-L-tyrosine N-oxide
4-Vinylphenol
Conditions | Yield |
---|---|
potassium acetate In N,N-dimethyl acetamide at 123℃; for 2.4h; Product distribution / selectivity; | 97% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
potassium acetate In N,N-dimethyl acetamide at 123℃; for 2.5h; Product distribution / selectivity; | A 4% B 96% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran -78 deg C, 10 min, reflux, 0.5 h; | 91% |
Conditions | Yield |
---|---|
With morpholine; 4-methoxy-phenol In N,N-dimethyl-formamide at 70℃; for 12h; | 89.4% |
Conditions | Yield |
---|---|
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In diethyl ether at 20℃; for 48h; Stille cross-coupling; | 84% |
Conditions | Yield |
---|---|
With dikegulac; water; urea hydrogen peroxide adduct In dichloromethane at 20℃; for 10h; Enzymatic reaction; | A 5% B 78% |
Conditions | Yield |
---|---|
With tris(triphenylphosphine)rhodium(l) chloride; triphenylphosphine; isopropyl alcohol In tetrahydrofuran at 25℃; for 8h; Reagent/catalyst; chemoselective reaction; | 78% |
Cl-Mo(O)=CH2
4-hydroxy-benzaldehyde
A
4-Vinylphenol
B
2-allylphenol
Conditions | Yield |
---|---|
With salicylaldehyde In tetrahydrofuran | A 21% B 77% |
Conditions | Yield |
---|---|
With 4-hydroxy-benzaldehyde In tetrahydrofuran | A 21% B 77% |
Conditions | Yield |
---|---|
With potassium hydroxide In isopropyl alcohol at 200℃; for 1.33333h; Reagent/catalyst; Time; | 76% |
Multi-step reaction with 3 steps 1: 100 percent / N,N-diisopropylethylamine / CH2Cl2 / 4 h 2: 97 percent / NaBH4 / aq. ethanol 3: 59 percent / 2-bromo-1,3,2-benzodioxaborole, N,N-diisopropylethylamine / CH2Cl2 / 3 h View Scheme | |
Multi-step reaction with 4 steps 1: aqueous NaOH 2: palladium/charcoal; methanol / 30 °C / 5884.06 Torr / Hydrogenation 3: acetic acid; Al2O3 / 350 °C / 25 Torr 4: aqueous KOH View Scheme |
Conditions | Yield |
---|---|
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 1.16667h; | 75% |
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 0.166667h; further catalyst; Yield given; |
N,N-dimethyl-L-tyrosine N-oxide
A
N,N-dimethylhydroxylamine
B
p-Coumaric Acid
C
4-Vinylphenol
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide at 130℃; Product distribution / selectivity; Cope Elimination; | A n/a B 75% C 3.3% |
Conditions | Yield |
---|---|
With sodium thioethylate In N,N-dimethyl-formamide for 0.5h; Heating; | 70% |
Conditions | Yield |
---|---|
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 14h; Schlenk technique; Inert atmosphere; | 67% |
1-(4-iodophenyl)ethanol
4-Vinylphenol
Conditions | Yield |
---|---|
With copper(l) iodide; 8-quinolinol; potassium hydroxide In water; dimethyl sulfoxide; tert-butyl alcohol at 100℃; for 48h; Inert atmosphere; | 60% |
(RS)-1-<4-(2-methoxyethoxy)methoxyphenyl>ethanol
4-Vinylphenol
Conditions | Yield |
---|---|
With bromocatecholborane; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; | 59% |
With bromocatecholborane; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Mechanism; | 59% |
methyl-triphenylphosphonium iodide
4-hydroxy-benzaldehyde
4-Vinylphenol
Conditions | Yield |
---|---|
Stage #1: methyl-triphenylphosphonium iodide With potassium tert-butylate In tetrahydrofuran for 1h; Inert atmosphere; Stage #2: 4-hydroxy-benzaldehyde In tetrahydrofuran at 25℃; for 24h; Wittig reaction; Inert atmosphere; | 58% |
With potassium tert-butylate In tetrahydrofuran Wittig Olefination; |
4-Vinylphenol
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 2h; UV-irradiation; | 52% |
3-(4-acetoxyphenyl)acrylic acid
4-Vinylphenol
Conditions | Yield |
---|---|
With aluminum oxide; potassium hydroxide; ammonium acetate In water for 0.166667h; microwave irradiation; | 49% |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 12h; Inert atmosphere; | 47% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 20℃; for 24h; Wittig Olefination; Green chemistry; | 47% |
4-Vinylphenol
H,ethyl (1-(N-tert-butoxycarbonylamino)-2-phenyl)ethylphosphonate
ethyl,4-ethenylphenyl (1-(N-tert-butoxycarbonylamino)-2-phenyl)ethylphosphonate
Conditions | Yield |
---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane Condensation; | 100% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 40℃; for 4h; Inert atmosphere; | 99.5% |
Conditions | Yield |
---|---|
With hydrogen In water at 70℃; under 7500.75 Torr; for 8h; Autoclave; | 99.2% |
Conditions | Yield |
---|---|
With hydrazine hydrate In acetonitrile at 30℃; for 24h; | 99% |
With hydrogen In methanol at 20℃; for 24h; chemoselective reaction; | 93% |
Multi-step reaction with 2 steps 1: 1 percent / Nocardia resting cells / aq. phosphate buffer / 48 h / 28 °C / pH 7.0 / Enzymatic reaction 2: Nocardia resting cells / aq. phosphate buffer / 24 h / 28 °C / pH 7.0 / Enzymatic reaction View Scheme |
tert-butyldimethylsilyl chloride
4-Vinylphenol
1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-ethenyl benzene
Conditions | Yield |
---|---|
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3h; | 99% |
In N,N-dimethyl-formamide at 0 - 20℃; for 24h; | 34 g |
1-bromo-2-(2-methoxyethoxy)ethane
4-Vinylphenol
Conditions | Yield |
---|---|
Stage #1: 4-Vinylphenol With potassium tert-butylate In acetonitrile for 1h; Reflux; Stage #2: 2-bromoethyl 2-methoxyethyl ether In acetonitrile for 6h; Reflux; Inert atmosphere; | 96% |
Stage #1: 4-Vinylphenol With potassium tert-butylate In acetonitrile for 1h; Reflux; Stage #2: 2-bromoethyl 2-methoxyethyl ether In acetonitrile for 6h; Inert atmosphere; Reflux; | 96% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 60℃; for 12h; Inert atmosphere; Schlenk technique; | 96% |
Conditions | Yield |
---|---|
Stage #1: 4-Vinylphenol With potassium tert-butylate In acetonitrile for 1h; Reflux; Stage #2: 2-chloroethyl methyl ether In acetonitrile for 6h; Reflux; Inert atmosphere; | 95% |
Stage #1: 4-Vinylphenol With potassium tert-butylate In acetonitrile for 1h; Stage #2: 2-chloroethyl methyl ether In acetonitrile for 6h; Inert atmosphere; | 95% |
(trifluoromethyl)trimethylsilane
4-Vinylphenol
Conditions | Yield |
---|---|
With sodium iodide In tetrahydrofuran at 65℃; Inert atmosphere; | 95% |
5-bromoresorcinol
4-Vinylphenol
(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol
Conditions | Yield |
---|---|
With {1,3-bis[2,6-bis(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}dichloro(pyridine)palladium; caesium carbonate In neat (no solvent) at 100℃; for 12h; Heck Reaction; | 93% |
methyl(phenyl)(divinyl)silane
4-Vinylphenol
Conditions | Yield |
---|---|
Stage #1: methyl(phenyl)(divinyl)silane; 4-Vinylphenol In dichloromethane at 40℃; for 0.25h; Inert atmosphere; Green chemistry; Stage #2: With Grubbs catalyst first generation In dichloromethane for 8h; Inert atmosphere; Green chemistry; | 92.5% |
Conditions | Yield |
---|---|
With triethylamine In diethyl ether for 2h; | 92% |
With triethylamine In diethyl ether for 2h; | 92% |
tert-butyl (4,4-dimethoxycyclohexa-2,5-dien-1-ylidene)carbamate
4-Vinylphenol
Conditions | Yield |
---|---|
With 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at 30℃; for 12h; regioselective reaction; | 92% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium hydroxide at 40℃; Temperature; Reagent/catalyst; Green chemistry; | 91.6% |
Conditions | Yield |
---|---|
With diphenyl hydrogen phosphate In 1,2-dichloro-ethane at 100℃; for 16h; regiospecific reaction; | 91% |
With diphenyl hydrogen phosphate In dichloromethane at 100℃; for 22h; | 1.22 g |
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 20 - 60℃; for 23h; | 91% |
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
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 . |
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-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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