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637-69-4

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637-69-4 Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

4-Methoxystyrene is employed in the ferric chloride-catalyzed addition of activated methylenes to styrenes. It acts as a monomer in polymerization reactions. Further, it is used to prepare 1,1,2,2-Tetracyano-3-(p-methoxyphenyl)cyclobutane by reacting with ethenetetracarbonitrile.

Synthesis Reference(s)

Chemistry Letters, 13, p. 1897, 1984The Journal of Organic Chemistry, 52, p. 422, 1987 DOI: 10.1021/jo00379a020Tetrahedron Letters, 35, p. 8773, 1994 DOI: 10.1016/S0040-4039(00)78494-2

Check Digit Verification of cas no

The CAS Registry Mumber 637-69-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 7 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 637-69:
(5*6)+(4*3)+(3*7)+(2*6)+(1*9)=84
84 % 10 = 4
So 637-69-4 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O/c1-3-8-4-6-9(10-2)7-5-8/h3-7H,1H2,2H3

637-69-4 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (B22353)  4-Methoxystyrene, 98%, stab. with 0.1% 4-tert-butylcatechol   

  • 637-69-4

  • 5g

  • 580.0CNY

  • Detail
  • Alfa Aesar

  • (B22353)  4-Methoxystyrene, 98%, stab. with 0.1% 4-tert-butylcatechol   

  • 637-69-4

  • 25g

  • 2041.0CNY

  • Detail
  • Alfa Aesar

  • (B22353)  4-Methoxystyrene, 98%, stab. with 0.1% 4-tert-butylcatechol   

  • 637-69-4

  • 100g

  • 6769.0CNY

  • Detail
  • Aldrich

  • (141003)  4-Vinylanisole  97%

  • 637-69-4

  • 141003-5G

  • 840.06CNY

  • Detail
  • Aldrich

  • (141003)  4-Vinylanisole  97%

  • 637-69-4

  • 141003-25G

  • 3,502.98CNY

  • Detail

637-69-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Methoxystyrene

1.2 Other means of identification

Product number -
Other names Benzene, 1-ethenyl-4-methoxy-

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:637-69-4 SDS

637-69-4Synthetic route

para-iodoanisole
696-62-8

para-iodoanisole

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 0.0833333h;100%
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 5h; further catalysts;73%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; zinc(II) chloride 1.) THF, RT, 20 min, 2.) RT, 1 h; Yield given. Multistep reaction;
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

tri-n-butyl(vinyl)tin
7486-35-3

tri-n-butyl(vinyl)tin

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With cesium fluoride; palladium diacetate In 1,4-dioxane at 100℃; for 3h; Stille cross-coupling;99%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; cesium fluoride; 3-tert-butyl-5-methyl-1-(2-(diphenylphosphino)phenyl)-1H-pyrazole In toluene at 60℃; for 10h; Stille coupling; Inert atmosphere;88%
With cesium fluoride In 1,4-dioxane at 100 - 110℃; for 22h; Stille Cross Coupling;80%
4-methoxyphenylacetylen
768-60-5

4-methoxyphenylacetylen

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With hydrogen; 3-azapentane-1,5-diamine In methanol at 25℃; for 6h;99%
With pyridine; hydrogen at 25℃; under 760.051 Torr; for 6h; Reagent/catalyst; Solvent; Green chemistry; chemoselective reaction;96%
With hydrogen In methanol at 20℃; for 40h; chemoselective reaction;95%
4-n-propylanisole
104-45-0

4-n-propylanisole

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With [CuCl(ClIPr)]; sodium t-butanolate; tert-butyl alcohol In tetrahydrofuran; hexane at 40℃; for 20h; Inert atmosphere; chemoselective reaction;99%
(vinyl)trimethoxylsilane
2768-02-7

(vinyl)trimethoxylsilane

para-iodoanisole
696-62-8

para-iodoanisole

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With 1-butyl-3-methyl-3H-imidazol-1-ium fluoride In acetonitrile at 70℃; Hiyama Coupling; Inert atmosphere;98%
With sodium hydroxide; 4-hydroxyacetophenone oxime-derived palladacycle In water at 120℃; for 0.166667h; Hiyama reaction; microwave irradiation;82%
With trans-[1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene]PdCl2(NC5H5); sodium hydroxide In 1,4-dioxane; water at 80℃; for 7h; Hiyama cross-coupling;41 %Chromat.
3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With sodium hydroxide; tributylmethylammonium bis(trifluoromethanesulfonyl)imide salt at 160℃; for 5h;97.5%
With 1,10-Phenanthroline; copper hydroxide In 1-methyl-pyrrolidin-2-one at 210℃; for 1h; Inert atmosphere; Green chemistry;68%
With copper(I) sulfate; copper(II) sulfate; hydroquinone In quinoline for 0.5h; Heating;29.1%
Triethoxyvinylsilane
78-08-0

Triethoxyvinylsilane

para-iodoanisole
696-62-8

para-iodoanisole

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 100℃; for 5h; Reagent/catalyst; Solvent; Temperature; Hiyama Coupling; Sealed tube;97%
With sodium hydroxide; 4-hydroxyacetophenone oxime-derived palladacycle In water at 120℃; for 0.166667h; Hiyama reaction; microwave irradiation;84%
With tetrabutyl ammonium fluoride; palladium dichloride In tetrahydrofuran at 65℃; for 9h; Hiyama coupling;78%
rac-1-(4-methoxyphenyl)-ethanol
3319-15-1

rac-1-(4-methoxyphenyl)-ethanol

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With potassium hydrogensulfate at 190℃; under 22 Torr; Pressure; Temperature; Large scale;96.3%
With phosphotungstic acid In dimethyl sulfoxide at 100℃; for 1h; Inert atmosphere;91%
With 1,1,1-trichloro-3,3,3-trifluoro-propan-2-one; toluene-4-sulfonic acid; hydroquinone In benzene for 10h; Heating;88%
4-methoxyphenylacetylen
768-60-5

4-methoxyphenylacetylen

A

4-Methoxystyrene
637-69-4

4-Methoxystyrene

B

p-ethylanisole
1515-95-3

p-ethylanisole

Conditions
ConditionsYield
With hydrogen In hexane at 50℃; under 760.051 Torr; for 10h;A 96%
B 4%
With hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;
With hydrogen In methanol at 25℃; for 2h;A 89 %Chromat.
B 11 %Chromat.
formaldehyd
50-00-0

formaldehyd

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
Stage #1: 4-Methoxybenzyl alcohol With triethylphosphine hydrobromide at 100℃; for 0.166667h; Microwave irradiation;
Stage #2: formaldehyd With potassium carbonate In water at 100℃; for 0.0833333h; Microwave irradiation;
96%
p-acetoxystyrene
2628-16-2

p-acetoxystyrene

methyl iodide
74-88-4

methyl iodide

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With potassium hydroxide In water; acetone at 20℃; for 124h;96%
tert-butyl (3R,αR)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-iodoheptanoate
1227062-94-3

tert-butyl (3R,αR)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-iodoheptanoate

A

4-Methoxystyrene
637-69-4

4-Methoxystyrene

B

tert-butyl (R)-2-[N(1)-benzylpiperidin-2-yl]acetate
1227062-91-0

tert-butyl (R)-2-[N(1)-benzylpiperidin-2-yl]acetate

Conditions
ConditionsYield
In acetonitrile at 80℃; for 16h;A 65%
B 94%
Cl-Mo(O)=CH2
84809-63-2

Cl-Mo(O)=CH2

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether 1) -70 deg C, 1-2 h, 2) -70 - 20 deg C, 15 h;93%
In tetrahydrofuran91%
In tetrahydrofuran; ethanol at -70℃; for 12h; Product distribution; use of var. solvents (H2O and H2O/EtOH), var. temp. and other reagent (Cl3Mo=CH2);92 % Chromat.
In tetrahydrofuran; ethanol for 12h; -70 degC to room temp.;92 % Chromat.
tetravinylsilane
1112-55-6

tetravinylsilane

para-iodoanisole
696-62-8

para-iodoanisole

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With palladium(II) acetylacetonate; potassium fluoride In N,N-dimethyl-formamide at 130℃; under 1500.15 Torr; for 3h; Reagent/catalyst; Time; Hiyama Coupling; Inert atmosphere;93%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere;
Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran Inert atmosphere;
91%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -78℃; for 2h;
Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at 20℃;
88.9%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran for 0.25h;
Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran Wittig olefination; Further stages.;
82%
4-methoxy-trans-cinnamaldehyde
24680-50-0, 71277-11-7, 1963-36-6

4-methoxy-trans-cinnamaldehyde

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With palladium 10% on activated carbon; oxygen; sodium carbonate In isopropyl alcohol at 120℃; for 24h; regioselective reaction;91%
With pyridine; palladium diacetate; triphenylphosphine In water at 100℃; for 24h; Inert atmosphere;72%
With palladium 10% on activated carbon; sodium carbonate In isopropyl alcohol at 120℃; for 6h; Inert atmosphere;
3-(p-methoxyphenyl)-1-propanol
5406-18-8

3-(p-methoxyphenyl)-1-propanol

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With methoxy(cyclooctadiene)rhodium(I) dimer; N,N-Dimethylacrylamide; 3-Methoxybenzoic acid; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 90℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; chemoselective reaction;91%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With Methyltriphenylphosphonium bromide; potassium carbonate In 1,4-dioxane at 100℃; for 16h; Microwave irradiation; Sealed tube; Inert atmosphere;90%
With aluminium silicate; acetic anhydride at 400℃;
Multi-step reaction with 3 steps
1: 85 percent / tetrahydrofuran
2: 96 percent / H2O2, (NH4)6MoO7*4H2O / ethanol / 65 h / Ambient temperature
3: 63 percent / LDA / tetrahydrofuran / 1) -78 deg C, 1 h, 2) r.t., 1 h
View Scheme
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

ethene
74-85-1

ethene

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With palladium diacetate; C22H27P; triethylamine In 1,4-dioxane; Hexadecane at 120℃; for 20h; Reagent/catalyst; Heck Reaction; Schlenk technique; Inert atmosphere; Autoclave;90%
With tributyl-amine; potassium carbonate; palladium In N,N-dimethyl-formamide at 150℃; under 7757.43 Torr; for 1h; Heck reaction; microwave irradiation;67%
With dichloro bis(acetonitrile) palladium(II); C9H13N3O; triethylamine In N,N-dimethyl-formamide at 160℃; under 4500.45 Torr; for 2h; Catalytic behavior; Heck Reaction; regioselective reaction;26%
With lithium perchlorate; triethylamine; triphenylphosphine In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide electrolysis;70 % Chromat.
With dichlorobis(tri-O-tolylphosphine)palladium; triethylamine In acetonitrile at 70℃; under 3345.86 Torr; Temperature; Reagent/catalyst; Heck Reaction;
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With Wilkinson's catalyst; isopropyl alcohol; 4-diphenylphosphanyl-benzoic acid 2-trimethylsilanyl-ethyl ester In tetrahydrofuran at 25℃; for 0.5h;90%
With (IMes)CuCl; triphenylphosphine; isopropyl alcohol In 1,4-dioxane; diethyl ether at 60℃; for 16h;82%
With tris(triphenylphosphine)rhodium(l) chloride; triphenylphosphine; isopropyl alcohol In tetrahydrofuran at 25℃; for 2h; Reagent/catalyst; chemoselective reaction;73%
With RhCl(PPh3)3; triphenylphosphine In 1,4-dioxane; isopropyl alcohol; toluene at 50℃;40 mg
para-iodoanisole
696-62-8

para-iodoanisole

4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane
4627-10-5

4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With silver(l) oxide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 67℃; for 24h; Suzuki-Miyaura reaction;90%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ClWO(CH2)
104644-08-8

ClWO(CH2)

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
In tetrahydrofuran at 66℃; for 1.5h;89%
4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

tri-n-butyl(vinyl)tin
7486-35-3

tri-n-butyl(vinyl)tin

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With P(i-BuNCH2CH2)2(BnNCH2CH2)N; dimethyl-N-fluoroamine; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100 - 110℃; Stille reaction;89%
With Pd((CH3)2C6H3NC(CH3)CHC(CH3)NC6H3(CH3)2)(CH3)(P(CH2CH3)3); cesium fluoride In tetrahydrofuran at 50℃; for 6h; Stille Cross Coupling;85%
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine; cesium fluoride In 1,4-dioxane at 100℃; for 48h; Stille cross-coupling;83%
Estragole
140-67-0

Estragole

ethene
74-85-1

ethene

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With Hoveyda-Grubbs catalyst second generation; di-μ-bromobis-(tritert-butylphosphine)dipalladium(I) In tetrahydrofuran at 60℃; under 7500.75 Torr; for 16h; Autoclave;89%
para-iodoanisole
696-62-8

para-iodoanisole

tri-n-butyl(vinyl)tin
7486-35-3

tri-n-butyl(vinyl)tin

4-Methoxystyrene
637-69-4

4-Methoxystyrene

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; copper(l) iodide; sodium chloride at 90℃; for 6h; other reagent: MnBr2, NaCl, N-methylpyrrolidone;88%
With palladium; N,N-dimethyl-formamide In 1-methyl-pyrrolidin-2-one at 120℃; for 15h;44%
With 9-phosphatriptycene deriv; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 2h; Stille coupling;64 % Spectr.
(R,S)-NN-dimethyl-N-phenacyl-1-p-methoxyphenylethylammonium bromide
87305-45-1

(R,S)-NN-dimethyl-N-phenacyl-1-p-methoxyphenylethylammonium bromide

A

4-Methoxystyrene
637-69-4

4-Methoxystyrene

B

4,4'-(butane-2,3-diyl)bis(methoxybenzene)
62224-36-6

4,4'-(butane-2,3-diyl)bis(methoxybenzene)

C

rac-1-(4-methoxyphenyl)-ethanol
3319-15-1

rac-1-(4-methoxyphenyl)-ethanol

D

2-dimethylamino-3-p-methoxyphenyl-1-phenylbutan-1-one
87258-60-4

2-dimethylamino-3-p-methoxyphenyl-1-phenylbutan-1-one

Conditions
ConditionsYield
With sodium hydroxide In water at 0℃; for 14h; Further byproducts given;A 0.4%
B 4%
C 1.1%
D 87%
With sodium hydroxide In water at 0℃; for 14h; Further byproducts given;A 0.4%
B 4%
C 1.1%
D 87%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; C21H19N5Pd(2+)*2BF4(1-) In decane; acetonitrile at 45℃; for 4h; Wacker Oxidation;100%
With water; oxygen In methanol; dimethyl sulfoxide at 80℃; under 1520.1 Torr; for 20h; Wacker Oxidation; Autoclave;99%
With palladium diacetate; 9-tert-butyl-10-methylanthracene ozonide In acetonitrile for 72h; Ambient temperature;93%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

p-ethylanisole
1515-95-3

p-ethylanisole

Conditions
ConditionsYield
With hydrogen; 1,5-hexadienerhodium(I)-chloride dimer In hexane for 7h; Ambient temperature; pH=7.6;100%
With C28H18Fe(1-)*K(1+)*C12H24O6*C4H8O; hydrogen In toluene at 60℃; under 1500.15 Torr; for 24h; Reagent/catalyst; Temperature; Pressure; Time; chemoselective reaction;100%
With hydrogen In d(4)-methanol at 20℃; under 760.051 Torr; for 6h;100%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

2-bromo-1-(4-methoxyphenyl)ethanol
117340-79-1

2-bromo-1-(4-methoxyphenyl)ethanol

Conditions
ConditionsYield
With N-Bromosuccinimide; water In acetonitrile at 20℃;100%
With N,N'-dibromo-N,N'-(1,2-ethanediyl)bis(p-toluenesulfonamide); ammonium acetate; water In acetone at 20℃; for 0.0333333h;95%
With hydrogen bromide; dimethyl sulfoxide In water at 60℃; for 12h;93%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

diisopropoxyphosphorylsulfenyl chloride
51756-01-5

diisopropoxyphosphorylsulfenyl chloride

Thiophosphoric acid S-[2-chloro-2-(4-methoxy-phenyl)-ethyl] ester O,O'-diisopropyl ester
139488-92-9

Thiophosphoric acid S-[2-chloro-2-(4-methoxy-phenyl)-ethyl] ester O,O'-diisopropyl ester

Conditions
ConditionsYield
In tetrachloromethane at 25℃; for 2h; Rate constant;100%
In tetrachloromethane at 25℃; for 2h;98%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

2-(4-methoxyphenyl)oxirane
6388-72-3

2-(4-methoxyphenyl)oxirane

Conditions
ConditionsYield
With 1H-imidazole; [MnIII(TPP)(OAc)]; tetra-n-butylammonium hydrogen monopersulfate In dichloromethane at 20℃; for 0.5h;100%
With dihydrogen peroxide In ethanol; water at 50℃; for 1h; Catalytic behavior; Green chemistry;99%
With dihydrogen peroxide; cobalt(II) acetate In water at 20℃; for 3h; Ionic liquid; Green chemistry;98%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With sodium periodate; C31H29Br2N3Ru*CH2Cl2 In water; ethyl acetate; acetonitrile at 25℃; for 0.5h; Inert atmosphere; Schlenk technique;100%
With ruthenium trichloride; [bis(acetoxy)iodo]benzene In dichloromethane; water at 30℃; for 2.5h; Solvent;92.1%
With dihydrogen peroxide In acetonitrile at 65℃; for 6h;92%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

[Y(η5:η1-C5Me4SiMe2NCMe3)(THF)(μ-H)]2

[Y(η5:η1-C5Me4SiMe2NCMe3)(THF)(μ-H)]2

[Y(η5:η1-C5Me4SiMe2NCMe3)(CH(CH3)C6H4-4-OMe)(THF)]

[Y(η5:η1-C5Me4SiMe2NCMe3)(CH(CH3)C6H4-4-OMe)(THF)]

Conditions
ConditionsYield
In benzene-d6 reaction in NMR tube, soln. was kept at room temp. for 2 h; solvent was removed in vac.; NMR;100%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

N-(4-hydroxyphenyl)-4-methylbenzenesulfonamide
1146-43-6

N-(4-hydroxyphenyl)-4-methylbenzenesulfonamide

N-(2-(4-methoxyphenyl)-2,3-dihydrobenzofuran-5-yl)-4-methylbenzenesulfonamide
1133046-88-4

N-(2-(4-methoxyphenyl)-2,3-dihydrobenzofuran-5-yl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene100%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

2-(4-methoxyphenyl)propionitrile
31007-06-4

2-(4-methoxyphenyl)propionitrile

Conditions
ConditionsYield
With 3-[bis-(4-methoxy-phenyl)-phosphanyl]-2H-isoquinolin-1-one; N-{6-[bis-(4-methoxy-phenyl)-phosphanyl]-pyridin-2-yl}-2,2-dimethyl-propionamide; bis(1,5-cyclooctadiene)nickel (0) In toluene at 35℃; for 25h; Inert atmosphere; regioselective reaction;100%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

1-(1-azido-2-chloroethyl)-4-methoxybenzene

1-(1-azido-2-chloroethyl)-4-methoxybenzene

Conditions
ConditionsYield
With 1-chloro-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; trimethylsilylazide; cesium fluoride In dichloromethane at 0℃; for 12h; Mechanism; Reagent/catalyst; Temperature; Solvent;100%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

4-Methoxystyrene
637-69-4

4-Methoxystyrene

(E)-4-cyano-4'-methoxystilbene
57193-97-2

(E)-4-cyano-4'-methoxystilbene

Conditions
ConditionsYield
With C28H24FN2O3PPd; tetrabutylammomium bromide; sodium acetate at 140℃; for 12h; Catalytic behavior; Inert atmosphere; Schlenk technique; regioselective reaction;100%
methanol
67-56-1

methanol

4-Methoxystyrene
637-69-4

4-Methoxystyrene

2-(4-methoxyphenyl)acetaldehyde dimethyl acetal
42866-92-2

2-(4-methoxyphenyl)acetaldehyde dimethyl acetal

Conditions
ConditionsYield
With Pyridine-2,6-dicarboxylic acid; iron(II) tetrafluoroborate hexahydrate; [bis(acetoxy)iodo]benzene at 20℃; for 20h; Molecular sieve; Inert atmosphere; regioselective reaction;99%
With ammonium iodide; Oxone at 30℃; for 3h; Green chemistry; regioselective reaction;78%
With thallium(III) nitrate
Stage #1: methanol; 4-Methoxystyrene With ammonium iodide for 0.0166667h; Inert atmosphere;
Stage #2: With Oxone at 30℃;
4-Methoxystyrene
637-69-4

4-Methoxystyrene

[N-(p-tolylsulfonyl)imino]phenyliodinane
55962-05-5

[N-(p-tolylsulfonyl)imino]phenyliodinane

2-(4-methoxyphenyl)-1-tosylaziridine
155721-36-1

2-(4-methoxyphenyl)-1-tosylaziridine

Conditions
ConditionsYield
With [CuI(tris[(tetramethylguanidino)-phenyl]amine)][PF6] In acetonitrile for 2h; Inert atmosphere; Molecular sieve;99%
With C12H18CuN6(2+)*2C16AlF36O4(1-) In acetonitrile at 25℃; for 0.0166667h; Inert atmosphere;93%
With iodine In water at 20℃; for 12h; Green chemistry;87%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

ethene
74-85-1

ethene

1-methoxy-4-(1-methyl-2-propenyl)benzene
18272-83-8

1-methoxy-4-(1-methyl-2-propenyl)benzene

Conditions
ConditionsYield
With 2-benzyloxymethylphenyldiphenylphosphine; bi(allylnickel bromide); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at 0 - 23℃; under 760.051 Torr; for 72h; Schlenk technique;99%
With hexakis(acetonitrile)nickel(II) tetrafluoroborate; diethylaluminium chloride; triphenylphosphine In dichloromethane; toluene at 20℃; under 7500.6 Torr; for 1h; hydrovinylation;76%
With 2; diethylaluminium chloride; triphenylphosphine In dichloromethane; toluene under 7500.6 Torr; for 0.5h; Yield given;
4-Methoxystyrene
637-69-4

4-Methoxystyrene

1-(4-methoxyphenyl) ethane-1,2-diol
32345-64-5, 147159-72-6, 147254-29-3, 13603-63-9

1-(4-methoxyphenyl) ethane-1,2-diol

Conditions
ConditionsYield
With dmap; osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone at 20℃;99%
Stage #1: 4-Methoxystyrene With formic acid; 2,6-dichloropyridine N-oxide; dichlororuthenium(IV) meso-tetrakis(2,6-dichlorophenyl)porphyrin In chloroform at 20℃; Darkness;
Stage #2: With potassium carbonate In methanol
95%
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; water; tert-butyl alcohol at 20℃; for 12h; Sealed tube;94%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

2-bromo-4-nitroaniline
13296-94-1

2-bromo-4-nitroaniline

2-amino-5-nitro-4'-methoxystilbene
178970-21-3

2-amino-5-nitro-4'-methoxystilbene

Conditions
ConditionsYield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 120℃; for 72h;99%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

2-carbonyl-3-butenenitrile
60556-87-8

2-carbonyl-3-butenenitrile

3,4-dihydro-2-(4-methoxyphenyl)-2H-pyran-6-carbonitrile

3,4-dihydro-2-(4-methoxyphenyl)-2H-pyran-6-carbonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 22h; hetero-Diels-Alder cycloaddition;99%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

A

(E)-1-methoxy-4-(4-nitrostyryl)benzene
4648-33-3

(E)-1-methoxy-4-(4-nitrostyryl)benzene

B

1-(4-methoxyphenyl)-1-(4-nitrophenyl)ethylene
28358-68-1

1-(4-methoxyphenyl)-1-(4-nitrophenyl)ethylene

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate; bis-<(4-Cl-2-PdCl-Ph)-(4-Cl-Ph)-methanone oxime> In N,N-dimethyl-formamide at 130℃; for 4h; Product distribution; Further Variations:; Reaction partners; Reagents; Temperatures; Heck-Mizoroki-Jeffery reaction;A 99%
B n/a
4-Methoxystyrene
637-69-4

4-Methoxystyrene

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

2-iodo-1-(3-methylbut-2-enyl)oxy-1-(4-methoxyphenyl)ethane

2-iodo-1-(3-methylbut-2-enyl)oxy-1-(4-methoxyphenyl)ethane

Conditions
ConditionsYield
With N-iodo-succinimide In dichloromethane at -78 - 0℃;99%
Stage #1: 4-Methoxystyrene; 3-methyl-2-buten-1-ol In dichloromethane at 20℃; for 0.0833333h;
Stage #2: With N-iodo-succinimide In dichloromethane at -78 - 0℃; Further stages.;
99%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

(E)-4,4'-(but-1-ene-1,3-diyl)bis(methoxybenzene)

(E)-4,4'-(but-1-ene-1,3-diyl)bis(methoxybenzene)

Conditions
ConditionsYield
With bromodichloromethane; sodium iodide In acetonitrile at 90℃; for 12h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere; Sealed tube;99%
With bis(acetylacetonato)palladium(II); trifluoroacetic acid In dichloromethane at 20℃; for 0.0833333h; stereoselective reaction;92%
With ethanol; triphenylphosphine; zinc; bis(triphenylphosphine)dichlorocobalt(II) In acetonitrile at 80℃; for 18h;82%
With ruthenium trichloride In tetrahydrofuran81%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

1-phenylmethylpiperazine
2759-28-6

1-phenylmethylpiperazine

N-benzyl-N'-[2-(4-methoxyphenyl)ethyl]piperazine
266674-64-0

N-benzyl-N'-[2-(4-methoxyphenyl)ethyl]piperazine

Conditions
ConditionsYield
Stage #1: 1-phenylmethylpiperazine With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.166667h;
Stage #2: 4-Methoxystyrene In tetrahydrofuran; hexane at 20℃; for 24h; Further stages.;
99%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

t-butyl diazoacetate
35059-50-8

t-butyl diazoacetate

tert-butyl (1R*,2S*)-2-(4-methoxyphenyl)cyclopropane-1-carboxylate

tert-butyl (1R*,2S*)-2-(4-methoxyphenyl)cyclopropane-1-carboxylate

Conditions
ConditionsYield
With C67H51IrN2O2 In tetrahydrofuran at -50℃; for 24.1667h; optical yield given as %ee; enantioselective reaction;99%
chiral phenyliridium(III)-salen complex In tetrahydrofuran at -50 - 20℃;99 % Spectr.
4-Methoxystyrene
637-69-4

4-Methoxystyrene

Ph3 P

Ph3 P

water
7732-18-5

water

2-(4-methoxyphenyl)propanoic acid
942-54-1

2-(4-methoxyphenyl)propanoic acid

Conditions
ConditionsYield
With CO In tetrahydrofuran99%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

ethene
74-85-1

ethene

1-methoxy-4-[(1S)-1-methylprop-2-en-1-yl]benzene

1-methoxy-4-[(1S)-1-methylprop-2-en-1-yl]benzene

Conditions
ConditionsYield
With bi(allylnickel bromide); C43H34NO2P; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at -78℃; under 760.051 Torr; for 1h; Reagent/catalyst;99%
With bi(allylnickel bromide); {benzyl[(S)-1-(1-naphthyl)ethyl]amino}[(R)-1,1'-binaphthyl-2,2'-diyldioxy]phosphine; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at -78℃; for 1h; Inert atmosphere; enantioselective reaction;
4-Methoxystyrene
637-69-4

4-Methoxystyrene

4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

1-(4-methoxystyryl)-4-fluorobenzene
39769-24-9

1-(4-methoxystyryl)-4-fluorobenzene

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2,5-di(2,4,6-trimethylphenyl)-1,2,5-thiadiazolidine-1-oxide; triethylamine In N,N-dimethyl-formamide at 200℃; for 0.166667h; Heck reaction; Microwave irradiation;99%
With tris-(dibenzylideneacetone)dipalladium(0); 2,5-di(2,4,6-trimethylphenyl)-1,2,5-thiadiazolidine-1-oxide; triethylamine In N,N-dimethyl-formamide at 200℃; for 0.166667h; Mizoroki-Heck reaction; Microwave irradiation;99%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

1-(4-methoxystyryl)-4-fluorobenzene
39769-24-9

1-(4-methoxystyryl)-4-fluorobenzene

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2,5-di(2,4,6-trimethylphenyl)-1,2,5-thiadiazolidine-1-oxide; tetrabutylammomium bromide; sodium acetate In 1-methyl-pyrrolidin-2-one at 200℃; for 0.5h; Heck reaction; Microwave irradiation;99%
With 2,5-di(2,4,6-trimethylphenyl)-1,2,5-thiadiazolidine-1-oxide; tetrabutylammomium bromide; sodium acetate; bis(dibenzylideneacetone)-palladium(0) In 1-methyl-pyrrolidin-2-one at 200℃; for 0.5h; Mizoroki-Heck reaction; Microwave irradiation;99%
With dichloro bis(acetonitrile) palladium(II); 10F6P(1-)*C235H200N20O10(10+); potassium hydroxide In 1-methyl-pyrrolidin-2-one at 160℃; for 5h; Heck Reaction; Inert atmosphere;95%
With potassium phosphate; C34H46Br4N8Pd2 In N,N-dimethyl-formamide at 110℃; for 4h; Heck Reaction;73%

637-69-4Relevant articles and documents

Hernandez,Chuchani

, p. 923,924, 926-927 (1978)

Functionalized styrene synthesis via palladium-catalyzed C[sbnd]C cleavage of aryl ketones

Dai, Hui-Xiong,Wang, Xing,Wang, Zhen-Yu,Xu, Hui,Zhang, Xu

supporting information, (2022/03/31)

We report herein the synthesis of functionalized styrenes via palladium-catalyzed Suzuki–Miyaura cross-coupling reaction between aryl ketone derivatives and potassium vinyltrifluoroborate. The employment of pyridine-oxazoline ligand was the key to the cleavage of unstrained C[sbnd]C bond. A variety of functional groups and biologically important moleculars were well tolerated. The orthogonal Suzuki–Miyaura coupling demonstrated the synthetic practicability.

A simple and efficientin situgenerated copper nanocatalyst for stereoselective semihydrogenation of alkynes

Park, Byoung Yong,Lim, Taeho,Han, Min Su

supporting information, p. 6891 - 6894 (2021/07/19)

Development of a simple, effective, and practical method for (Z)-selective semihydrogenation of alkynes has been considered necessary for easy-to-access applications at organic laboratory scales. Herein, (Z)-selective semihydrogenation of alkynes was achieved using a copper nanocatalyst which was generatedin situsimply by adding ammonia borane to an ethanol solution of copper sulfate. Different types of alkynes including aryl-aryl, aryl-alkyl, and aliphatic alkynes were selectively reduced to (Z)-alkenes affording up to 99% isolated yield. The semihydrogenation of terminal alkynes to alkenes and gram-scale applications were also reported. In addition to eliminating catalyst preparation, the proposed approach is simple and practical and serves as a suitable alternative method to the conventional Lindlar catalyst.

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