Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 4h; Reflux; | 99% |
With water; potassium hydroxide In methanol Reflux; | 93% |
With potassium hydroxide In methanol; water for 6h; Heating; | 81% |
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutylammomium bromide; water at 125℃; for 0.333333h; | 98% |
With cetyltrimethylammonim bromide; sodium hydroxide In water at 125℃; for 0.666667h; | 95% |
With tetrabutylammomium bromide; sodium hydroxide In water at 125℃; for 2h; Inert atmosphere; | 57% |
Conditions | Yield |
---|---|
With C46H49CoN3P4(2+)*2BF4(1-); hydrogen; potassium hydroxide In ethanol; acetonitrile at 60℃; under 22801.5 Torr; for 24h; Autoclave; Glovebox; chemoselective reaction; | 95% |
With sodium tetrahydroborate In methanol at 0 - 25℃; for 2h; Inert atmosphere; | 92% |
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; tris[3,5-bis(trifluoromethyl)phenyl]-borane In 1,4-dioxane at 25℃; for 12h; Glovebox; | 66% |
(4-ethynylphenyl)methanol
(4-vinyl-phenyl)-methanol
Conditions | Yield |
---|---|
With hydrogen In acetonitrile at 110℃; under 7500.75 Torr; for 15h; chemoselective reaction; | 94% |
With bis-triphenylphosphine-palladium(II) chloride; tri-n-butyl-tin hydride In tetrahydrofuran at 20℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 0.166667h; Inert atmosphere; Cooling with ice; | 91% |
Conditions | Yield |
---|---|
With caesium carbonate; triphenylphosphine; palladium dichloride In tetrahydrofuran; water at 85℃; for 22h; Suzuki-Miyaura reaction; | 82% |
4-Vinylbenzyl chloride
A
(4-vinyl-phenyl)-methanol
B
di(4-vinylbenzyl)ether
Conditions | Yield |
---|---|
With sodium hydroxide; water In ethanol at 20℃; for 24h; | A 19% B 81% |
(4-vinyl-phenyl)-methanol
Conditions | Yield |
---|---|
With methanol at 20℃; for 0.5h; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
With palladium diacetate; tetra-(n-butyl)ammonium iodide; triethylamine; CyJohnPhos In N,N-dimethyl-formamide; toluene at 120℃; under 11251.1 Torr; for 0.333333h; Mizoroki-Heck coupling; | 78% |
With palladium diacetate; tetra-(n-butyl)ammonium iodide; triethylamine; johnphos In N,N-dimethyl-formamide; toluene at 120℃; under 11251.1 Torr; for 0.333333h; Heck Reaction; | 78% |
Conditions | Yield |
---|---|
With phenylsilane; C34H30CoO6; potassium In tetrahydrofuran at 20℃; for 20h; Inert atmosphere; Schlenk technique; Glovebox; | 64% |
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; | 62% |
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; | 62% |
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; | 62% |
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 25℃; for 1h; Inert atmosphere; | 423 mg |
2,4,6,8-tetramethyl-2,4,6,8-tetravinyl-cyclotetrasiloxane
4-bromobenzenemethanol
(4-vinyl-phenyl)-methanol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; palladium(II) bromide; johnphos In tetrahydrofuran at 50℃; for 14h; | 54% |
1-(2-chloroethyl)-4-(chloromethyl)benzene
(4-vinyl-phenyl)-methanol
Conditions | Yield |
---|---|
With sodium hydroxide; hydroquinone In ethanol |
1,1-dibromo-2-(4-methoxycarbonylphenyl)ethene
A
(4-vinyl-phenyl)-methanol
B
(E)-1-bromo-2-(4-hydroxymethylphenyl)ethene
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; ethyl acetate In tetrahydrofuran at -40℃; for 12h; |
4-acetoxymethyl-(1-(R,S)-acetoxyethyl)benzene
(4-vinyl-phenyl)-methanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: steam / 475 - 500 °C / 25 - 30 Torr / Leiten ueber Silicagel 2: ethanolic KOH; sulfur; hydroquinone View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HCl, ZnCl2 / CS2 2: aq. NaOH, benzene-1,4-diol / ethanol View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: magnesium; iodine / tetrahydrofuran / 4.5 h / 0 - 25 °C / Inert atmosphere 1.2: 3 h 2.1: lithium aluminium tetrahydride / diethyl ether; tetrahydrofuran / 1 h / 0 - 25 °C / Inert atmosphere View Scheme |
(4-ethynylphenyl)methanol
A
(4-vinyl-phenyl)-methanol
B
4-ethylbenzyl alcohol
Conditions | Yield |
---|---|
With nickel(II) nitrate hexahydrate; hydrogen In acetonitrile at 120℃; under 22502.3 Torr; for 15h; Overall yield = 86 %; |
Conditions | Yield |
---|---|
With oxalyl dichloride; dimethyl sulfoxide; triethylamine at -60℃; for 0.333333h; Swern oxidation; | 100% |
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃; Inert atmosphere; | 4.2 g |
With phosphoric acid In water; toluene at 25℃; under 760.051 Torr; for 24h; pH=3.4; Irradiation; Inert atmosphere; Sealed tube; | 63 %Spectr. |
Stage #1: (4-vinyl-phenyl)-methanol With Quinuclidine; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; oxygen; tetrabutylammonium dihydrogen phosphate In 1,2-dichloro-ethane for 0.25h; Molecular sieve; Stage #2: In 1,2-dichloro-ethane for 9h; Molecular sieve; Irradiation; |
oxirane
succinic acid anhydride
(4-vinyl-phenyl)-methanol
poly(ethylene glycol), α-terminated with vinylbenzyloxy group, ω-terminated with 2-carboxylatoethylcarboxy group, potassium salt, Mn 8E3 Da, Mw/Mn 1.08; monomer(s): 4-vinylbenzyl alcohol; ethylene oxide; succinic anhydride
Conditions | Yield |
---|---|
Stage #1: oxirane; (4-vinyl-phenyl)-methanol With potassium enolate of acetone In tetrahydrofuran Stage #2: succinic acid anhydride In tetrahydrofuran | 99% |
(4-vinyl-phenyl)-methanol
1-(bromomethyl)-4-vinylbenzene
Conditions | Yield |
---|---|
With phosphorus tribromide In diethyl ether at 0℃; for 2h; | 96% |
With phosphorus tribromide In diethyl ether at 0 - 20℃; for 2h; | 78% |
With phosphorus tribromide In diethyl ether at 0 - 20℃; for 2h; Appel Halogenation; Inert atmosphere; |
oxirane
succinic acid anhydride
(4-vinyl-phenyl)-methanol
poly(ethylene glycol), α-terminated with vinylbenzyloxy group, ω-terminated with 2-carboxylatoethylcarboxy group, potassium salt, Mn 4.2E3 Da, Mw/Mn 1.06; monomer(s): 4-vinylbenzyl alcohol; ethylene oxide; succinic anhydride
Conditions | Yield |
---|---|
Stage #1: oxirane; (4-vinyl-phenyl)-methanol With potassium enolate of acetone In tetrahydrofuran Stage #2: succinic acid anhydride In tetrahydrofuran | 96% |
oxirane
succinic acid anhydride
(4-vinyl-phenyl)-methanol
poly(ethylene glycol), α-terminated with vinylbenzyloxy group, ω-terminated with 2-carboxylatoethylcarboxy group, potassium salt, Mn 2.9E3 Da, Mw/Mn 1.07; monomer(s): 4-vinylbenzyl alcohol; ethylene oxide; succinic anhydride
Conditions | Yield |
---|---|
Stage #1: oxirane; (4-vinyl-phenyl)-methanol With potassium enolate of acetone In tetrahydrofuran Stage #2: succinic acid anhydride In tetrahydrofuran | 95% |
Conditions | Yield |
---|---|
With aminosulfonic acid at 20℃; for 24h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With copper; sodium carbonate In N,N-dimethyl-formamide at 79.84℃; Catalytic behavior; Heck Reaction; Glovebox; | 93% |
oxirane
succinic acid anhydride
(4-vinyl-phenyl)-methanol
poly(ethylene glycol), α-terminated with vinylbenzyloxy group, ω-terminated with 2-carboxylatoethylcarboxy group, potassium salt, Mn 2.1E3 Da, Mw/Mn 1.06; monomer(s): 4-vinylbenzyl alcohol; ethylene oxide; succinic anhydride
Conditions | Yield |
---|---|
Stage #1: oxirane; (4-vinyl-phenyl)-methanol With potassium enolate of acetone In tetrahydrofuran Stage #2: succinic acid anhydride In tetrahydrofuran | 91% |
(4-vinyl-phenyl)-methanol
perfluoro-2,5-dimethyl-3,6-dioxanonanoyl fluoride
C18H9F17O4
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; | 91% |
methanol
(4-vinyl-phenyl)-methanol
(Difluoromethyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
With fac-tris(2-phenylpyridinato-N,C2')iridium(III) at 20℃; for 11h; Schlenk technique; Inert atmosphere; Irradiation; | 91% |
Conditions | Yield |
---|---|
With tetrakis(actonitrile)copper(I) hexafluorophosphate; tris(1,10-phenathrolinyl)ruthenium(II) hexafluorophosphate; 2-[4,5-dihydrooxazolin-2'-yl]quinoline; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; Sealed tube; Irradiation; | 91% |
(4-vinyl-phenyl)-methanol
diphenyl(4-vinylphenyl)phosphine
1,4-bis[4-(vinyl)phenoxy]butane
poly(4-styryldiphenylphosphine-co-[4-vinylbenzyl alcohol]-co-1,4-bis[4-vinylphenoxy]butane); monomer(s): 4-styryldiphenylphosphine; 4-vinylbenzyl alcohol; 1,4-bis(4-vinylphenyl)butane
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); sodium chloride; acacia gum In water; chlorobenzene at 85℃; for 20h; | 90% |
(4-vinyl-phenyl)-methanol
Conditions | Yield |
---|---|
Stage #1: (4-vinyl-phenyl)-methanol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: dimethyl 2-((fluoromethyl)(phenyl)-l4-sulfaneylidene)malonate In N,N-dimethyl-formamide; mineral oil at 20℃; for 12h; Schlenk technique; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
With oxygen In toluene at 90℃; Reagent/catalyst; Sealed tube; | 90% |
oxirane
succinic acid anhydride
(4-vinyl-phenyl)-methanol
poly(ethylene glycol), α-terminated with vinylbenzyloxy group, ω-terminated with 2-carboxylatoethylcarboxy group, potassium salt, Mn 5.3E3 Da, Mw/Mn 1.14; monomer(s): 4-vinylbenzyl alcohol; ethylene oxide; succinic anhydride
Conditions | Yield |
---|---|
Stage #1: oxirane; (4-vinyl-phenyl)-methanol With Naphthalene anion ( K(1+) is the counterion) Stage #2: succinic acid anhydride | 88% |
Conditions | Yield |
---|---|
With [copper(I)(2,9-di(4-methoxyphenyl)-1,10-phenanthroline)2] hexafluorophosphate; potassium hydrogencarbonate at 20℃; for 1h; Inert atmosphere; Schlenk technique; Irradiation; | 87% |
(4-vinyl-phenyl)-methanol
tert-butyldimethylsilyl chloride
O-(tert-butyl)dimethylsilyl(4-vinylphenyl)methanol
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 48h; Inert atmosphere; | 86% |
(4-vinyl-phenyl)-methanol
Conditions | Yield |
---|---|
With potassium 2-(difluoro(trifluoromethoxy)methoxy)-2,2-difluoroacetate; tetramethylammonium fluoride at 150℃; for 5h; Glovebox; Inert atmosphere; Schlenk technique; Sealed tube; | 85% |
With potassium 2-(difluoro(trifluoromethoxy)methoxy)-2,2-difluoroacetate; tetramethylammonium fluoride at 150℃; for 5h; Schlenk technique; Glovebox; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With oxalyl dichloride; Tropone In dichloromethane at 20℃; for 0.25h; Inert atmosphere; | 84% |
(4-vinyl-phenyl)-methanol
toluene-4-sulfonamide
4-methyl-N-(4-vinylbenzyl)benzenesulfonamide
Conditions | Yield |
---|---|
With (bis[(2-diisopropylphosphino)ethyl]amine)Mn(CO)2Br; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 24h; Sealed tube; chemoselective reaction; | 84% |
(4-vinyl-phenyl)-methanol
O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane for 0.166667h; | 83% |
(4-vinyl-phenyl)-methanol
Conditions | Yield |
---|---|
With hydrogen bromide; dimethyl sulfoxide In water at 60℃; for 12h; | 83% |
With water; hydrogen bromide In dimethyl sulfoxide at 60℃; for 12h; Schlenk technique; | 83% |
Conditions | Yield |
---|---|
With oxygen at 120℃; for 16h; Green chemistry; | 83% |
Conditions | Yield |
---|---|
With oxygen In toluene at 90℃; Sealed tube; | 82% |
The (4-Vinylphenyl)methanol, with the CAS registry number 1074-61-9, has the systematic name of (4-ethenylphenyl)methanol. It belongs to the product category of API intermediate. And the molecular formula of this chemical is C9H10O.
The physical properties of (4-Vinylphenyl)methanol are as following: (1)ACD/LogP: 1.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.52; (4)ACD/LogD (pH 7.4): 1.52; (5)ACD/BCF (pH 5.5): 8.36; (6)ACD/BCF (pH 7.4): 8.36; (7)ACD/KOC (pH 5.5): 159.11; (8)ACD/KOC (pH 7.4): 159.11; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 20.23 Å2; (13)Index of Refraction: 1.59; (14)Molar Refractivity: 43.62 cm3; (15)Molar Volume: 129.1 cm3; (16)Polarizability: 17.29×10-24cm3; (17)Surface Tension: 40.4 dyne/cm; (18)Density: 1.038 g/cm3; (19)Flash Point: 115.4 °C; (20)Enthalpy of Vaporization: 51.17 kJ/mol; (21)Boiling Point: 247.1 °C at 760 mmHg; (22)Vapour Pressure: 0.0139 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: OCc1ccc(C=C)cc1
(2)InChI: InChI=1/C9H10O/c1-2-8-3-5-9(7-10)6-4-8/h2-6,10H,1,7H2
(3)InChIKey: CLECMSNCZUMKLM-UHFFFAOYAH
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