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(4-Vinylphenyl)methanol, with the molecular formula C9H10O, is a colorless liquid characterized by a sweet, floral scent. It is recognized for its versatile applications across different industries, primarily as a fragrance ingredient in personal care products and perfumes. Additionally, it serves as a precursor in the synthesis of a range of chemicals, including pharmaceuticals, agrochemicals, and polymer materials. Due to its potential as a skin and eye irritant, careful handling and storage in well-ventilated areas are essential.

1074-61-9

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1074-61-9 Usage

Uses

Used in Fragrance Industry:
(4-Vinylphenyl)methanol is used as a fragrance ingredient for its sweet, floral odor, enhancing the sensory appeal of various personal care products and perfumes.
Used in Chemical Synthesis:
(4-Vinylphenyl)methanol is used as a precursor in the synthesis of other chemicals, such as pharmaceuticals, agrochemicals, and polymer materials, due to its reactive vinyl group that facilitates chemical reactions.
Used in Pharmaceutical Industry:
(4-Vinylphenyl)methanol is used as a building block in the development of pharmaceutical compounds, contributing to the creation of new medications for various health conditions.
Used in Agrochemical Industry:
(4-Vinylphenyl)methanol is utilized in the synthesis of agrochemicals, playing a role in the production of pesticides and other agricultural chemicals to protect crops and enhance yield.
Used in Polymer Industry:
(4-Vinylphenyl)methanol is employed in the production of polymer materials, where its vinyl group is polymerized to form polymers with specific properties for use in various applications.

Check Digit Verification of cas no

The CAS Registry Mumber 1074-61-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,7 and 4 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1074-61:
(6*1)+(5*0)+(4*7)+(3*4)+(2*6)+(1*1)=59
59 % 10 = 9
So 1074-61-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O/c1-2-8-3-5-9(7-10)6-4-8/h2-6,10H,1,7H2

1074-61-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (4-ethenylphenyl)methanol

1.2 Other means of identification

Product number -
Other names (4-vinylphenyl)methanol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1074-61-9 SDS

1074-61-9Synthetic route

4-acetoxymethylstyrene
1592-12-7

4-acetoxymethylstyrene

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
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%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
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%
4-vinyl-benzaldehyde
1791-26-0

4-vinyl-benzaldehyde

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
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
10602-04-7

(4-ethynylphenyl)methanol

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
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;
methyl 4-vinylbenzoate
1076-96-6

methyl 4-vinylbenzoate

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 0.166667h; Inert atmosphere; Cooling with ice;91%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

potassium vinyltrifluoroborate

potassium vinyltrifluoroborate

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
With caesium carbonate; triphenylphosphine; palladium dichloride In tetrahydrofuran; water at 85℃; for 22h; Suzuki-Miyaura reaction;82%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

A

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

B

di(4-vinylbenzyl)ether
115444-35-4

di(4-vinylbenzyl)ether

Conditions
ConditionsYield
With sodium hydroxide; water In ethanol at 20℃; for 24h;A 19%
B 81%
2-(4-vinylbenzyloxy)pinacolborane

2-(4-vinylbenzyloxy)pinacolborane

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
With methanol at 20℃; for 0.5h; Inert atmosphere;80%
ethene
74-85-1

ethene

4-iodo-benzyl alcohol
18282-51-4

4-iodo-benzyl alcohol

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
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%
4-ethenylbenzoic acid
1075-49-6

4-ethenylbenzoic acid

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
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
2554-06-5

2,4,6,8-tetramethyl-2,4,6,8-tetravinyl-cyclotetrasiloxane

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; palladium(II) bromide; johnphos In tetrahydrofuran at 50℃; for 14h;54%
1-(2-chloroethyl)-4-(chloromethyl)benzene
53459-40-8

1-(2-chloroethyl)-4-(chloromethyl)benzene

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
With sodium hydroxide; hydroquinone In ethanol
1,1-dibromo-2-(4-methoxycarbonylphenyl)ethene
253684-21-8

1,1-dibromo-2-(4-methoxycarbonylphenyl)ethene

A

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

B

(E)-1-bromo-2-(4-hydroxymethylphenyl)ethene
117417-08-0

(E)-1-bromo-2-(4-hydroxymethylphenyl)ethene

C

(Z)-1-bromo-2-(4-hydroxymethylphenyl)ethene

(Z)-1-bromo-2-(4-hydroxymethylphenyl)ethene

Conditions
ConditionsYield
With lithium aluminium tetrahydride; ethyl acetate In tetrahydrofuran at -40℃; for 12h;
4-acetoxymethyl-(1-(R,S)-acetoxyethyl)benzene
256449-39-5

4-acetoxymethyl-(1-(R,S)-acetoxyethyl)benzene

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: steam / 475 - 500 °C / 25 - 30 Torr / Leiten ueber Silicagel
2: ethanolic KOH; sulfur; hydroquinone
View Scheme
2-phenylethyl chloride
622-24-2

2-phenylethyl chloride

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl, ZnCl2 / CS2
2: aq. NaOH, benzene-1,4-diol / ethanol
View Scheme
1-bromo-4-ethenyl-benzene
2039-82-9

1-bromo-4-ethenyl-benzene

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

Conditions
ConditionsYield
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
10602-04-7

(4-ethynylphenyl)methanol

A

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

B

4-ethylbenzyl alcohol
768-59-2

4-ethylbenzyl alcohol

Conditions
ConditionsYield
With nickel(II) nitrate hexahydrate; hydrogen In acetonitrile at 120℃; under 22502.3 Torr; for 15h; Overall yield = 86 %;
(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

4-vinyl-benzaldehyde
1791-26-0

4-vinyl-benzaldehyde

Conditions
ConditionsYield
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
75-21-8

oxirane

succinic acid anhydride
108-30-5

succinic acid anhydride

(4-vinyl-phenyl)-methanol
1074-61-9

(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

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
ConditionsYield
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
1074-61-9

(4-vinyl-phenyl)-methanol

1-(bromomethyl)-4-vinylbenzene
13368-25-7

1-(bromomethyl)-4-vinylbenzene

Conditions
ConditionsYield
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
75-21-8

oxirane

succinic acid anhydride
108-30-5

succinic acid anhydride

(4-vinyl-phenyl)-methanol
1074-61-9

(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

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
ConditionsYield
Stage #1: oxirane; (4-vinyl-phenyl)-methanol With potassium enolate of acetone In tetrahydrofuran
Stage #2: succinic acid anhydride In tetrahydrofuran
96%
oxirane
75-21-8

oxirane

succinic acid anhydride
108-30-5

succinic acid anhydride

(4-vinyl-phenyl)-methanol
1074-61-9

(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

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
ConditionsYield
Stage #1: oxirane; (4-vinyl-phenyl)-methanol With potassium enolate of acetone In tetrahydrofuran
Stage #2: succinic acid anhydride In tetrahydrofuran
95%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

2-[(4-vinylbenzyl)oxy]tetrahydro-2H-pyran

2-[(4-vinylbenzyl)oxy]tetrahydro-2H-pyran

Conditions
ConditionsYield
With aminosulfonic acid at 20℃; for 24h; Inert atmosphere;94%
1-iodocyclohexane
626-62-0

1-iodocyclohexane

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

C15H20O

C15H20O

Conditions
ConditionsYield
With copper; sodium carbonate In N,N-dimethyl-formamide at 79.84℃; Catalytic behavior; Heck Reaction; Glovebox;93%
oxirane
75-21-8

oxirane

succinic acid anhydride
108-30-5

succinic acid anhydride

(4-vinyl-phenyl)-methanol
1074-61-9

(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

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
ConditionsYield
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
1074-61-9

(4-vinyl-phenyl)-methanol

perfluoro-2,5-dimethyl-3,6-dioxanonanoyl fluoride
2641-34-1

perfluoro-2,5-dimethyl-3,6-dioxanonanoyl fluoride

C18H9F17O4
1191466-44-0

C18H9F17O4

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;91%
methanol
67-56-1

methanol

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

(Difluoromethyl)triphenylphosphonium bromide
58310-28-4

(Difluoromethyl)triphenylphosphonium bromide

(4-(3,3-difluoro-1-methoxypropyl)phenyl)methanol

(4-(3,3-difluoro-1-methoxypropyl)phenyl)methanol

Conditions
ConditionsYield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III) at 20℃; for 11h; Schlenk technique; Inert atmosphere; Irradiation;91%
(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

di(4-methyl)phenylthiosulfonate
2943-42-2

di(4-methyl)phenylthiosulfonate

(4-(1-(p-tolylthio)-2-tosylethyl)phenyl)methanol

(4-(1-(p-tolylthio)-2-tosylethyl)phenyl)methanol

Conditions
ConditionsYield
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
1074-61-9

(4-vinyl-phenyl)-methanol

diphenyl(4-vinylphenyl)phosphine
40538-11-2

diphenyl(4-vinylphenyl)phosphine

1,4-bis[4-(vinyl)phenoxy]butane
112309-98-5

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

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
ConditionsYield
With 2,2'-azobis(isobutyronitrile); sodium chloride; acacia gum In water; chlorobenzene at 85℃; for 20h;90%
(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

dimethyl 2-((fluoromethyl)(phenyl)-l4-sulfaneylidene)malonate

dimethyl 2-((fluoromethyl)(phenyl)-l4-sulfaneylidene)malonate

1-((fluoromethoxy)methyl)-4-vinylbenzene

1-((fluoromethoxy)methyl)-4-vinylbenzene

Conditions
ConditionsYield
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%
(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

4-amino-o-xylene
95-64-7

4-amino-o-xylene

C17H17N

C17H17N

Conditions
ConditionsYield
With oxygen In toluene at 90℃; Reagent/catalyst; Sealed tube;90%
oxirane
75-21-8

oxirane

succinic acid anhydride
108-30-5

succinic acid anhydride

(4-vinyl-phenyl)-methanol
1074-61-9

(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

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
ConditionsYield
Stage #1: oxirane; (4-vinyl-phenyl)-methanol With Naphthalene anion ( K(1+) is the counterion)
Stage #2: succinic acid anhydride
88%
methanol
67-56-1

methanol

(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

[3-(methoxycarbonyl)pyridinium-1-yloxy](trifluoromethyl)difluoroborate

[3-(methoxycarbonyl)pyridinium-1-yloxy](trifluoromethyl)difluoroborate

[4-(3,3,3-trifluoro-1-methoxypropyl)phenyl]methanol

[4-(3,3,3-trifluoro-1-methoxypropyl)phenyl]methanol

Conditions
ConditionsYield
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
1074-61-9

(4-vinyl-phenyl)-methanol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

O-(tert-butyl)dimethylsilyl(4-vinylphenyl)methanol
149636-62-4

O-(tert-butyl)dimethylsilyl(4-vinylphenyl)methanol

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 48h; Inert atmosphere;86%
(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

1-(fluoromethyl)-4-vinylbenzene

1-(fluoromethyl)-4-vinylbenzene

Conditions
ConditionsYield
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%
(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; Tropone In dichloromethane at 20℃; for 0.25h; Inert atmosphere;84%
(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

4-methyl-N-(4-vinylbenzyl)benzenesulfonamide
1217489-64-9

4-methyl-N-(4-vinylbenzyl)benzenesulfonamide

Conditions
ConditionsYield
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
1074-61-9

(4-vinyl-phenyl)-methanol

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate
74808-10-9

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

4-vinylbenzyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

4-vinylbenzyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane for 0.166667h;83%
(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

2-bromo-1-(4-(hydroxymethyl)phenyl)ethanol

2-bromo-1-(4-(hydroxymethyl)phenyl)ethanol

Conditions
ConditionsYield
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%
(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

4-ethenylbenzoic acid
1075-49-6

4-ethenylbenzoic acid

Conditions
ConditionsYield
With oxygen at 120℃; for 16h; Green chemistry;83%
(4-vinyl-phenyl)-methanol
1074-61-9

(4-vinyl-phenyl)-methanol

3-methoxypropylamine
5332-73-0

3-methoxypropylamine

C13H17NO

C13H17NO

Conditions
ConditionsYield
With oxygen In toluene at 90℃; Sealed tube;82%

1074-61-9Relevant articles and documents

Bifunctional polymeric organocatalysts and their application in the cooperative catalysis of Morita-Baylis-Hillman reactions

Kwong, Cathy Kar-Wing,Huang, Rui,Zhang, Minjuan,Shi, Min,Toy, Patrick H.

, p. 2369 - 2376 (2007)

A series of soluble, noncross-linked polystyrene-supported tri-phenylphosphane and 4-dimethylaminopyridine reagents were prepared. Some of these polymeric reagents contained either alkyl alcohol or phenol groups on the polymer backbone. The use of these materials as organocatalysts in a range of Morita-Baylis-Hillman reactions indicated that hydroxyl groups could participate in the reactions and accelerate product formation. In the cases examined, phenol groups were more effective than alkyl alcohol groups for catalyzing the reactions. This article is one of the first reports of the synthesis and use of non-natural, bifunctional polymeric reagents for use in organic synthesis in which both functional groups can cooperatively participate in the catalysis of reactions.

Mechanistic Study of Palladium-Catalyzed Hydroesterificative Copolymerization of Vinyl Benzyl Alcohol and CO

Yee, Gereon M.,Wang, Tong,Hillmyer, Marc A.,Tonks, Ian A.

, p. 1778 - 1786 (2019)

The copolymerization of vinyl benzyl alcohol (VBA) and carbon monoxide (CO) to give a new polyester poly(VBA-CO) has been achieved via palladium-catalyzed hydroesterification. Reaction conditions involve moderate temperatures, moderate to low CO pressures, and low catalyst loadings to give a low molar mass (Mn 3-4 kg/mol) polymer as a 2:1 mixture of linear to branched repeat units. The polymer molar mass increase is consistent with a step-growth polymerization mechanism, and ester yields of >97% are achieved within 24 h. However, increases in Mn cease beyond 16 h. Control experiments indicate that the degree of polymerization is limited due to a combination of side reactions such as alcoholic end-group oxidation, hydroxycarbonylation, and alcohol acetylation, which lead to the degradation of monomeric and polymeric end groups. When a less promiscuous substrate is used such as 10-undecenol, higher molar masses (Mn 16 kg/mol) are achieved. This method has the potential to be a mild route to new polyester architectures with appropriate mitigation of side reactions.

Synthesis and application of polytetrahydrofuran-grafted polystyrene (PS-PTHF) resin supports for organic synthesis

Shimomura, Osamu,Se Lee, Byoung,Meth, Sergio,Suzuki, Hiroki,Mahajan, Suresh,Nomura, Ryoki,Janda, Kim D.

, p. 12160 - 12167 (2005)

Cross-linked polystyrene (PS) with polytetrahydrofuran (PTHF) chains were prepared for use in solid phase organic synthesis (SPOS). The resins were prepared from styrene, styrene-PTHF macromonomers and cross-linkers 1,4-bis[4-vinylphenoxy]butane or divinylbenzene by suspension polymerization. The styrene-PTHF macromonomers were prepared by cationic polymerization of 4-vinylbenzyl bromide and 4-(4-vinylphenoxy)butyl iodide activated by silver hexafluoroantimonate and 4-(5-hydroxypentyl)styrene activated by triflic anhydride. Alternatively, polytetrahydrofuran-grafted polystyrene (PS-PTHF) resins could also be directly prepared from 5-hydroxypentyl JandaJel by cationic polymerization using triflic anhydride as the initiator. These PS-PTHF resins exhibited good swelling characteristics across a wide spectrum of polar and non-polar solvents. These resins were used in the synthesis of 3-methyl-1-phenyl-2-pyrazolin-5-one, which requires β-ketoester formation at low temperature (-78°C), resulting in good yield and product purity; whereas the same synthesis carried out on PEG-grafted PS (PS-PEG) resin resulted in incomplete synthesis.

Aromatic Nitrogen Mustard-Based Autofluorescent Amphiphilic Brush Copolymer as pH-Responsive Drug Delivery Vehicle

Saha, Biswajit,Choudhury, Neha,Seal, Soma,Ruidas, Bhuban,De, Priyadarsi

, p. 546 - 557 (2019)

Delivery of clinically approved nonfluorescent drugs is facing challenges because it is difficult to monitor the intracellular drug delivery without incorporating any integrated fluorescence moiety into the drug carrier. The present investigation reports the synthesis of a pH-responsive autofluorescent polymeric nanoscaffold for the administration of nonfluorescent aromatic nitrogen mustard chlorambucil (CBL) drug into the cancer cells. Copolymerization of poly(ethylene glycol) (PEG) appended styrene and CBL conjugated N-substituted maleimide monomers enables the formation of well-defined luminescent alternating copolymer. These amphiphilic brush copolymers self-organized in aqueous medium into 25-68 nm nanoparticles, where the CBL drug is enclosed into the core of the self-assembled nanoparticles. In vitro studies revealed ~70% drug was retained under physiological conditions at pH 7.4 and 37 °C. At endolysosomal pH 5.0, 90% of the CBL was released by the pH-induced cleavage of the aliphatic ester linkages connecting CBL to the maleimide unit. Although the nascent nanoparticle (without drug conjugation) is nontoxic, the drug conjugated nanoparticle showed higher toxicity and superior cell killing capability in cervical cancer (HeLa) cells rather than in normal cells. Interestingly, the copolymer without any conventional chromophore exhibited photoluminescence under UV light irradiation due to the presence of "through-space" π- π interaction between the C=O group of maleimide unit and the adjacent benzene ring of the styrenic monomer. This property helped us intracellular tracking of CBL conjugated autofluorescent nanocarriers through fluorescence microscope imaging. Finally, the 4-(4-nitrobenzyl)pyridine (NBP) colorimetric assay was executed to examine the ability of CBL-based polymeric nanomaterials toward alkylation of DNA.

High refractive index transparent nanocomposites prepared by in situ polymerization

Tsai, Chieh-Ming,Hsu, Sheng-Hao,Ho, Chun-Chih,Tu, Yu-Chieh,Tsai, Hsin-Chien,Wang, Chung-An,Su, Wei-Fang

, p. 2251 - 2258 (2014)

High refractive index transparent nanocomposites have been developed by in situ polymerization of a precursor that contains functional monomers and surface modified anatase TiO2 nanoparticles for optoelectronic applications. The monomers are in the liquid form, so environmentally friendly solventless precursors can be prepared. The precursor can be processed into various shapes or thick films (>50 microns) of the nanocomposite. The relationships of the chemical structure of the organic matrix, nanoparticle content and dispersity with the refractive index, transparency, mechanical and thermal properties are systematically investigated. The refractive index, and mechanical and thermal properties of the nanocomposite are increased with increasing TiO2 content and aromatic structure in the organic matrix due to their rigid characteristics. The transparency of the nanocomposite is increased with increasing TiO2 content and dispersity. At the same loading of nanoparticles, the higher dispersity and the better transparency are due to the less extent of Rayleigh scattering. At 18 vol% (60 wt%) of TiO2, the acetic acid modified TiO2/poly(4-vinyl benzyl alcohol) nanocomposite has a refractive index of 1.73 and excellent transparency (>85% from 500 nm to 800 nm). The refractive index of the nanocomposite can be further increased to 1.77 by replacing aliphatic acetic acid modified TiO2 with aromatic phenyl acetic acid modified TiO2. The results of this work provide new knowledge and a new pathway to design a polymer based high refractive index material.

The formation of core cross-linked star polymers containing cores cross-linked by dynamic covalent imine bonds

Jackson, Alexander W.,Fulton, David A.

, p. 6051 - 6053 (2010)

Diblock copolymers possessing amino or aldehyde functions within one of their blocks were prepared using RAFT polymerization techniques. These polymers were shown to cross-link through dynamic imine bonds to form core cross-linked star polymers which display a size-dependency upon the concentration at which the cross-linking reactions are performed.

Optimization of polystyrene-supported triphenylphosphine catalysts for aza-Morita-Baylis-Hillman reactions

Zhao, Lin-Jing,Kwong, Cathy Kar-Wing,Shi, Min,Toy, Patrick H.

, p. 12026 - 12032 (2005)

A series of polar group functionalized polystyrene-supported phosphine reagents were examined as catalysts in the aza-Morita-Baylis-Hillman reactions of N-tosyl arylimines and a variety of Michael acceptors with the aim of identifying the optimal polymer/solvent combination. For these reactions JandaJel-PPh3 (1 mmol PPh3/g loading) resin containing methoxy groups (JJ-OMe-PPh3) on the polystyrene backbone in THF solvent provided the highest yield of all the catalyst/solvent combinations examined. The methyl ether groups were incorporated into JJ-OMe-PPh3 using commercially available 4-methoxystyrene, and thus such polar polystyrene resins are easily accessible and should find utility as nucleophilic catalyst supports.

N-Doping of thermally polymerizable fullerenes as an electron transporting layer for inverted polymer solar cells

Cho, Namchul,Yip, Hin-Lap,Hau, Steven K.,Chen, Kung-Shih,Kim, Tae-Wook,Davies, Joshua A.,Zeigler, David F.,Jen, Alex K.-Y.

, p. 6956 - 6961 (2011)

A novel [6,6]-phenyl-C61-butyric acid methyl styryl ester (PCBM-S) was synthesized and employed as an electron transporting interfacial layer for bulk heterojunction polymer solar cells with an inverted device configuration. After the deposition of PCBM-S film from solution, the styryl groups of PCBM-S were polymerized by post-thermal treatment to form a robust film which is resistive to common organic solvents. This allows the solution processing of upper bulk heterojunction film without eroding the PCBM-S layer. Additionally, the PCBM-S was n-doped with decamethylcobaltocene (DMC) to increase the conductivity of the film, which resulted in a significantly improved power conversion efficiency from 1.24% to 2.33%. The improved device performance is due to the decrease of series resistance and improved electron extraction property of the n-doped PCBM-S film.

Controlling Multiple Active Sites on Pd?CeO2 for Sequential C?C Cross-coupling and Alcohol Oxidation in One Reaction System

Antink, Wytse Hooch,Bok, Jinsol,Cho, Sung-Pyo,Choi, Hyunwoo,Hyeon, Taeghwan,Jung, Yoon,Kim, Do Heui,Kim, Jiheon,Kim, Jongchan,Kim, Ju Hee,Kim, Sumin,Kim, Young Gyu,Ko, Wonjae,Kwak, Minjoon,Lee, Byoung-Hoon,Lee, Chan Woo,Lee, Eunwon,Lee, Kug-Seung,Lee, Seong Chan,Yim, Guk Hee,Yoo, Dongwon

, (2022/01/22)

Ceria (CeO2)-supported metal catalysts have been widely utilized for various single-step chemical transformations. However, using such catalysts for a multistep organic reaction in one reaction system has rarely been achieved. Here, we investigate multiple active sites on Pd?CeO2 catalysts and optimize them for a multistep reaction of C?C cross-coupling and alcohol oxidation. Atomic-level imaging and spectroscopic studies reveal that metallic Pd0 and Pd?CeO2 interface are active sites on Pd?CeO2 for C?C cross-coupling and oxidation, respectively. These active sites are controlled under the structural evolution of Pd?CeO2 during reductive heat-treatments. Accordingly, we found that optimally reduced Pd?CeO2 catalysts containing ~1.5 nm-sized Pd nanoclusters with both sites in balance are ideal for multistep chemical transformations in one reaction system. Our strategy to design supported metal catalysts leads to one-pot sequential synthetic protocols for pharmaceutical building blocks.

A method of synthesis of alcohols

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Paragraph 0079-0084, (2022/01/10)

The present invention belongs to the field of organic synthesis technology, specifically a synthesis method of an alcohol; the present invention is under the catalytic action of tert-butanol lithium, with ester compounds and pinacol borane as raw materials, tetrahydrofuran as a solvent, reacted at 100 ° C for 24h, followed by adding 2mol / LNaOH / MeOH solution, stirred at room temperature overnight to obtain alcohol compounds; the raw materials of the present invention are of extensive sources or easy to prepare, the reaction conditions are relatively mild and do not require a large number of / cumbersome additives, in addition to the tert-butanol lithium catalyst is simple, And the prepared alcohol compounds are of high quality and high separation yield.

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