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58-72-0 Usage

Chemical Properties

White to slightly beige powder

Uses

Triphenylethylene is used in preparation of Esterase activated aggregation-induced luminescent anticancer prodrug.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 82, 1956 DOI: 10.1021/ja01582a025Organic Syntheses, Coll. Vol. 2, p. 606, 1943Tetrahedron Letters, 14, p. 4193, 1973

Safety Profile

Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 58-72-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 8 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 58-72:
(4*5)+(3*8)+(2*7)+(1*2)=60
60 % 10 = 0
So 58-72-0 is a valid CAS Registry Number.
InChI:InChI=1/C20H16/c1-4-10-17(11-5-1)16-20(18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-16H

58-72-0 Well-known Company Product Price

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  • Alfa Aesar

  • (A13244)  Triphenylethylene, 98+%   

  • 58-72-0

  • 10g

  • 342.0CNY

  • Detail
  • Alfa Aesar

  • (A13244)  Triphenylethylene, 98+%   

  • 58-72-0

  • 50g

  • 1347.0CNY

  • Detail
  • Alfa Aesar

  • (A13244)  Triphenylethylene, 98+%   

  • 58-72-0

  • 250g

  • 5338.0CNY

  • Detail

58-72-0SDS

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 Triphenylethylene

1.2 Other means of identification

Product number -
Other names 1,2-diphenylethenylbenzene

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:58-72-0 SDS

58-72-0Synthetic route

sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

diphenyl acetylene
501-65-5

diphenyl acetylene

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With water; acetic acid; bis-triphenylphosphine-palladium(II) chloride at 20℃; for 6h;100%
With bis-triphenylphosphine-palladium(II) chloride; water; acetic acid at 20℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube;94%
iodobenzene
591-50-4

iodobenzene

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 70℃; for 4h; Suzuki-Miyaura Coupling;100%
1-dimethyl(2-pyridyl)silyl-1,2,3-triphenylethene
384360-11-6

1-dimethyl(2-pyridyl)silyl-1,2,3-triphenylethene

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃; for 1h;99%
Triphenylvinyl bromide
1607-57-4

Triphenylvinyl bromide

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With tetraethylammonium perchlorate; triethylamine In ethanol; dimethyl sulfoxide at 20℃; for 18h; Electrolysis; Green chemistry;98%
With lithium aluminium tetrahydride; nickel dichloride In tetrahydrofuran < 0 deg C;95%
With lithium aluminium tetrahydride; nickel dichloride In tetrahydrofuran Product distribution; < 0 deg C; other triarylvinyl halogenides, other transition metal halides;95%
With 2,3-diethynylquinoxaline; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 25℃; Product distribution; Rate constant; Thermodynamic data; -1.2 V vs. Ag/AgI; various mediators; indirect electrochemical reduction of vinyl halides and related compounds; rate constants and free energies of activation for electron transfer from electrochemically generated anion radicals to vinyl halides;
With Diethyl phosphonate; tert-butyl alcohol In acetonitrile at 25℃; Product distribution; Kinetics; Further Variations:; Solvents;
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

diphenyl acetylene
501-65-5

diphenyl acetylene

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
Stage #1: phenylmagnesium bromide; diphenyl acetylene With nickel(II) chloride hexahydrate In tetrahydrofuran; toluene at 20℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #2: With water In tetrahydrofuran; toluene Catalytic behavior; Reagent/catalyst; Solvent; Concentration; Inert atmosphere; Schlenk technique;
98%
With manganese(ll) chloride In tetrahydrofuran; toluene at 100℃; for 4h;60%
Stage #1: phenylmagnesium bromide; diphenyl acetylene With 1,1'-bis-(diphenylphosphino)ferrocene; iron(III)-acetylacetonate; 1,2-dichloro-2-methylpropane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #2: With hydrogenchloride In tetrahydrofuran; water Catalytic behavior; Reagent/catalyst;
24 %Chromat.
styrene
292638-84-7

styrene

iodobenzene
591-50-4

iodobenzene

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With silver(I) acetate; palladium diacetate; acetic acid at 110℃; for 6h; Heck reaction;97%
With dipalladium(II)(1,1'-di-t-butyl-3,3'-(1,2-ethanediyl)bisimidazolium)dipyridinetetradichloride; tetrabutylammomium bromide; sodium acetate In N,N-dimethyl acetamide at 120℃; for 18h; Heck Reaction; Inert atmosphere;71%
benzophenone
119-61-9

benzophenone

O,O-diethyl benzylphosphonate
1080-32-6

O,O-diethyl benzylphosphonate

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With 15-crown-5; sodium hydride In tetrahydrofuran at 0 - 25℃; for 3h;96%
With potassium tert-butylate; toluene
iodobenzene
591-50-4

iodobenzene

phenylacetylene
536-74-3

phenylacetylene

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With triethylamine; bis(acetato)bis(triphenylphosphine)palladium(0) In acetonitrile at 80℃; for 3.5h;96%
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; chlorobenzene In ethanol at 70℃; for 2h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique;80%
1,2,2-triphenyl-1-iodoethylene
22021-09-6

1,2,2-triphenyl-1-iodoethylene

A

Triphenylethylene
58-72-0

Triphenylethylene

B

9-Benzylidene-9H-fluorene
1836-87-9

9-Benzylidene-9H-fluorene

Conditions
ConditionsYield
With palladium diacetate; cesium pivalate; bis-diphenylphosphinomethane In N,N-dimethyl-formamide at 100℃; for 24h;A 4%
B 96%
With sodium acetate; dimethyl amine; bis-diphenylphosphinomethane; palladium diacetate at 100℃; for 36h;A 48%
B 52%
diphenyl acetylene
501-65-5

diphenyl acetylene

phenylboronic acid
98-80-6

phenylboronic acid

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With (N,N-diisopropylamino)diphenylphosphine; potassium carbonate; palladium dichloride In tetrahydrofuran at 20 - 65℃; Inert atmosphere;96%
With acetic acid; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 12h;91%
With water; palladium diacetate; bis(pinacol)diborane; tricyclohexylphosphine In tetrahydrofuran at 80℃; for 4h;90%
(E)-1,2-diphenyl-ethene
103-30-0

(E)-1,2-diphenyl-ethene

phenylboronic acid
98-80-6

phenylboronic acid

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With potassium fluoride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium diacetate; propionic acid at 20℃; for 1h; sealed tube;95%
With palladium diacetate; sodium acetate In acetic acid at 25℃; for 27h;69 % Chromat.
bromobenzene
108-86-1

bromobenzene

diphenyl acetylene
501-65-5

diphenyl acetylene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

Triphenylethylene
58-72-0

Triphenylethylene

B

1,1,2,2-tetraphenylethylene
632-51-9

1,1,2,2-tetraphenylethylene

Conditions
ConditionsYield
Stage #1: diphenyl acetylene; bis(pinacol)diborane With tetrakis(triphenylphosphine)platinum In 1,4-dioxane at 180℃; for 0.5h; microwave irradiation;
Stage #2: bromobenzene With palladium diacetate; potassium hydroxide; triphenylphosphine In 1,4-dioxane at 140℃; for 0.5h; Suzuki cross-coupling reaction; microwave irradiation; Further stages.;
A n/a
B 95%
2-phenyl[1,3,2]dioxaborolane
4406-72-8

2-phenyl[1,3,2]dioxaborolane

1-bromo-2-(1-phenylpropen-1-yl)benzene
24892-82-8

1-bromo-2-(1-phenylpropen-1-yl)benzene

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With tris(o-methoxyphenyl)phosphine; palladium diacetate; palladium; cesium pivalate In tetrahydrofuran at 110℃; for 3h; Schlenk technique; Inert atmosphere;95%
2,3,3-triphenylacrylonitrile
6304-33-2

2,3,3-triphenylacrylonitrile

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; ethanol; potassium hexamethylsilazane In toluene at 150℃; for 8h; Inert atmosphere; Molecular sieve;95%
(E)-1-bromo-1,2-diphenylethene
14447-41-7

(E)-1-bromo-1,2-diphenylethene

phenylboronic acid
98-80-6

phenylboronic acid

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With potassium hydroxide; triphenylphosphine; palladium diacetate In tetrahydrofuran; methanol at 25℃; for 1h; Suzuki cross-coupling;94%
benzophenone tosylhydrazone
4545-20-4

benzophenone tosylhydrazone

benzyl bromide
100-39-0

benzyl bromide

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; lithium tert-butoxide In toluene at 80℃; for 3h; Inert atmosphere;94%
bromobenzene
108-86-1

bromobenzene

potassium 3,3-diphenylacrylate
1619921-49-1

potassium 3,3-diphenylacrylate

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With palladium(II) acetylacetonate; N,N,N,N,-tetramethylethylenediamine; copper(I) bromide In 1-methyl-pyrrolidin-2-one at 170℃; for 16h; Inert atmosphere;94%
1,1,2-Triphenylethanol
4428-13-1

1,1,2-Triphenylethanol

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
iodine at 60℃; for 4h;93%
With potassium hydrogensulfate at 155 - 160℃;
With acetic acid
iodobenzene
591-50-4

iodobenzene

diphenyl acetylene
501-65-5

diphenyl acetylene

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; cesium acetate; copper diacetate In tetrahydrofuran at 80℃; for 24h; Reagent/catalyst; diastereoselective reaction;93%
With formic acid; triethylamine; bis(acetato)bis(triphenylphosphine)palladium(0) In acetonitrile at 80℃; for 6.5h; Product distribution; Mechanism; reaction with various aryl iodides;87%
With formic acid; triethylamine; bis(acetato)bis(triphenylphosphine)palladium(0) In acetonitrile at 80℃; for 6.5h;87%
Stage #1: diphenyl acetylene With ethylmagnesium bromide; iron(II) chloride In diethyl ether at 20℃; for 0.25h; Inert atmosphere;
Stage #2: iodobenzene With bis(triphenylphosphine)nickel(II) chloride In diethyl ether at 20℃; for 3.5h; Inert atmosphere;
Stage #3: With hydrogenchloride; water In diethyl ether
80%
With sodium; triphenylphosphine; palladium diacetate In methanol at 25℃; for 24h;64%
iodobenzene
591-50-4

iodobenzene

(E)-1,2-diphenyl-ethene
103-30-0

(E)-1,2-diphenyl-ethene

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 120℃; for 24h; Heck Reaction; Inert atmosphere;93%
With silver(I) acetate; palladium diacetate; acetic acid at 110℃; for 0.5h; Heck reaction;92%
With silver(I) acetate; palladium diacetate In acetic acid at 110℃; for 2h;88%
diphenyl acetylene
501-65-5

diphenyl acetylene

benzene
71-43-2

benzene

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With hafnium(IV) trifluoromethanesulfonate; 1-n-butyl-3-methylimidazolium hexafluoroantimonate at 85℃; for 1h; Friedel-Crafts alkenylation;92%
With 1-n-butyl-3-methylimidazolium hexafluoroantimonate; hafnium(IV) trifluoromethanesulfonate at 85℃; for 1h; Friedel-Crafts alkenylation;92%
With tributyl borane; Pd2(p-Tol)2(μ-OH)(μ-dpfam) In tetrahydrofuran at 120℃; for 17h;64%
phenyl trimethylsiloxane
2996-92-1

phenyl trimethylsiloxane

diphenyl acetylene
501-65-5

diphenyl acetylene

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
Stage #1: phenyl trimethylsiloxane; diphenyl acetylene With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetrabutyl ammonium fluoride; copper diacetate; triphenylphosphine In toluene at 20℃; for 2h;
Stage #2: With water In toluene at 110℃; for 12h;
92%
bromobenzene
108-86-1

bromobenzene

caesium 3,3-diphenylacrylate
1619921-50-4

caesium 3,3-diphenylacrylate

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With palladium(II) acetylacetonate; N,N,N,N,-tetramethylethylenediamine; copper(I) bromide at 140℃; for 16h; Inert atmosphere;92%
3-(2,2,2-triphenylethoxy)-3-chlorodiazirine
913723-48-5

3-(2,2,2-triphenylethoxy)-3-chlorodiazirine

A

C21H18Cl2O

C21H18Cl2O

B

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
In chloroform-d1 for 2h; Photolysis; Title compound not separated from byproducts;A 9%
B 91%
Triphenylvinyl bromide
1607-57-4

Triphenylvinyl bromide

ethylzinc chloride
2633-75-2

ethylzinc chloride

A

Triphenylethylene
58-72-0

Triphenylethylene

B

but-1-ene-1,1,2-triyltribenzene
63019-13-6

but-1-ene-1,1,2-triyltribenzene

Conditions
ConditionsYield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate at 100℃; Product distribution; Further Variations:; Reagents; Catalysts; Temperatures; Negishi coupling;A n/a
B 91%
phenylacetylene
536-74-3

phenylacetylene

phenylboronic acid
98-80-6

phenylboronic acid

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
acetylacetonatodicarbonylrhodium(l) In water; toluene at 110℃; for 12h; Product distribution; Further Variations:; Catalysts; Solvents;90%
sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

diphenyl acetylene
501-65-5

diphenyl acetylene

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With palladium diacetate; trifluoroacetic acid; naphthalene-1,8-diamine In 1,4-dioxane; water at 120℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube;90%
diphenyl acetylene
501-65-5

diphenyl acetylene

benzoic acid
65-85-0

benzoic acid

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With [bis(acetato)-(η-p-cymene)-ruthenium] In 1,4-dioxane; n-heptane; 1,3,5-trimethyl-benzene at 80℃; for 48h; Inert atmosphere; Sealed tube; regioselective reaction;90%
With α-picoline; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; guanidinium carbonate; acetic acid In toluene at 120℃; Inert atmosphere;62%
With [Ru(O2CMes)2(p-cymene)]; vanadia In toluene at 100℃; for 24h; Inert atmosphere;43%
bromobenzene
108-86-1

bromobenzene

(E)-1,2-diphenyl-ethene
103-30-0

(E)-1,2-diphenyl-ethene

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 130℃; for 48h; Heck reaction; Inert atmosphere;89%
With C24H26N4O2Pd2*2ClO4(1-); sodium acetate In 1-methyl-pyrrolidin-2-one at 140℃; Sealed tube; Air;61%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 150℃; for 48h; Heck Reaction; Inert atmosphere;24%
With {2,6-bis[(di-1-piperidinylphosphino)amino]phenyl}palladium(II) chloride; potassium carbonate In N,N-dimethyl-formamide; toluene at 160℃; for 20h; Heck reaction; Inert atmosphere;
With {2,6-bis[(di-1-piperidinylphosphino)amino]phenyl}palladium(II) chloride; potassium carbonate In N,N-dimethyl-formamide; toluene at 160℃; for 20h; Mizoroki-Heck reaction; Inert atmosphere;
triphenylboroxine
3262-89-3

triphenylboroxine

(E)-1-(trimethylacetoxy)-1,2-diphenylethylene

(E)-1-(trimethylacetoxy)-1,2-diphenylethylene

Triphenylethylene
58-72-0

Triphenylethylene

Conditions
ConditionsYield
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride; water In 1,4-dioxane; toluene at 110℃; for 20h; Suzuki-Miyaura coupling; Inert atmosphere;89%
Triphenylethylene
58-72-0

Triphenylethylene

chlorotriphenylethylene
18084-97-4

chlorotriphenylethylene

Conditions
ConditionsYield
With aluminium trichloride; benzeneseleninyl chloride In dichloromethane Ambient temperature;100%
With aluminium trichloride; benzeneseleninyl chloride In dichloromethane for 3h; Ambient temperature;100%
With phosphorus pentachloride at 190 - 200℃;
Triphenylethylene
58-72-0

Triphenylethylene

1,1,2-triphenylethane
1520-42-9

1,1,2-triphenylethane

Conditions
ConditionsYield
With n-butyllithium; [(1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene)FeCl2]; hydrogen In toluene at 80℃; under 7500.75 Torr; for 16h; Sealed tube;99%
Stage #1: Triphenylethylene With lithium triethylborohydride; cobalt(II) bromide In tetrahydrofuran Inert atmosphere; Glovebox;
Stage #2: With hydrogen In tetrahydrofuran at 20℃; under 1500.15 Torr; for 3h; Reagent/catalyst;
99%
With iodine; hypophosphorous acid In acetic acid for 24h; Heating;97%
Triphenylethylene
58-72-0

Triphenylethylene

2,2,3-triphenyloxirane
4479-98-5

2,2,3-triphenyloxirane

Conditions
ConditionsYield
With (NMe4)(Co-ortho-phenylenebis(N'-methyloxamidate)*2H2O*CH3CN; oxygen; pivalaldehyde In fluorobenzene for 2h; Ambient temperature;98%
With Oxone; edetate disodium; sodium hydrogencarbonate; 1,1-dioxotetrahydrothiopyran-4-one In acetonitrile for 6h; Ambient temperature;97%
With rhodium(II) acetate dimer; oxygen; isobutyraldehyde In acetone at 20℃; for 0.5h;95%
Triphenylethylene
58-72-0

Triphenylethylene

2-fluoro-1,1,2-triphenylethanol
137742-63-3

2-fluoro-1,1,2-triphenylethanol

Conditions
ConditionsYield
With water; N-fluorobis<(trifluoromethyl)sulfonyl>imide In dichloromethane at 0℃; for 1.5h;98%
With Selectfluor; water In acetonitrile for 0.0333333h; Microwave irradiation; regioselective reaction;95%
With water; 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate) In acetonitrile at 35℃; for 0.5h;98 % Spectr.
Triphenylethylene
58-72-0

Triphenylethylene

Triphenylvinyl bromide
1607-57-4

Triphenylvinyl bromide

Conditions
ConditionsYield
With aluminum tri-bromide; benzeneseleninyl chloride In dichloromethane for 3h; Ambient temperature;97%
With bromine In chloroform at -78℃; for 6h;87%
Stage #1: Triphenylethylene With bromine In chloroform at 20℃; for 1.5h;
Stage #2: With triethylamine In chloroform at 20℃;
87%
Triphenylethylene
58-72-0

Triphenylethylene

1,2-difluoro-1,1,2-triphenylethane
125440-38-2

1,2-difluoro-1,1,2-triphenylethane

Conditions
ConditionsYield
With (HF)nPy; N-fluorobis<(trifluoromethyl)sulfonyl>imide In dichloromethane at 0℃; for 2h;96%
With xenon difluoride; hydrogen fluoride In dichloromethane for 1h;44%
With silver fluoride; titanium(IV) oxide In acetonitrile for 48h; Ambient temperature; Irradiation;7 % Spectr.
Triphenylethylene
58-72-0

Triphenylethylene

C20H16(2)H2

C20H16(2)H2

Conditions
ConditionsYield
With palladium on activated charcoal; tetrabutylammomium bromide; water-d2; cesium fluoride; silicon at 100℃; for 24h;96%
Stage #1: Triphenylethylene With sodium In tetrahydrofuran Inert atmosphere;
Stage #2: With water-d2 In tetrahydrofuran Inert atmosphere;
Triphenylethylene
58-72-0

Triphenylethylene

9-phenylphenanthrene
844-20-2

9-phenylphenanthrene

Conditions
ConditionsYield
With {Co(II)(DBF2)2(H2O)2} In acetonitrile at 20℃; for 18h; Sealed tube; UV-irradiation; Inert atmosphere;94%
With cyclohexane; iodine Irradiation.UV-Licht;
palladium diacetate; palladium dichloride In 1,4-dioxane; acetic acid Heating;
With iodine; oxygen In cyclohexane Irradiation;
In ethanol Irradiation;
methanol
67-56-1

methanol

Triphenylethylene
58-72-0

Triphenylethylene

2-fluoro-1-methoxy-1,1,2-triphenylethane

2-fluoro-1-methoxy-1,1,2-triphenylethane

Conditions
ConditionsYield
With Selectfluor In acetonitrile for 0.025h; Microwave irradiation; regioselective reaction;94%
With Selectfluor In acetonitrile at 22℃; for 1h; Yield given;
With 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate) In acetonitrile at 35℃; for 0.5h;97 % Spectr.
With 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate) In acetonitrile at 24℃; Kinetics; Fluorination; Nucleophilic addition;
With Selectfluor

58-72-0Relevant articles and documents

Visible-light-induced photoredox-catalyzed synthesis of benzimidazo[2,1-a]iso-quinoline-6(5H)-ones

Wang, Bin,Zou, Long,Wang, Lei,Sun, Manman,Li, Pinhua

, p. 1229 - 1232 (2021)

A simple and efficient visible-light-induced photoredox-catalyzed diarylation of N-methacryloyl-2-arylbenzoimidazoles with aryl diazonium salts was developed. The reaction provides a convenient access to a variety of benzimidazoisoquinolinones through the construction of two C[sbnd]C bonds in one step under mild reaction conditions.

Zimmerman,Munch

, p. 187,190 (1968)

Pd-Catalyzed Coupling of N-Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes

Zhang, Kena,Provot, Olivier,Alami, Mouad,Tran, Christine,Hamze, Abdallah

supporting information, p. 1249 - 1261 (2022/02/07)

This study shows that various di- and tri-substituted alkenes with high chemoselectivity were obtained in good to high yields by coupling N-tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consis

Oxime ligands for Pd catalysis of the Mizoroki–Heck reaction, Suzuki–Miyaura coupling & annulation reactions

Bangar, Pronnoy G.,Nahide, Pradip D.,Meroliya, Heena K.,Waghmode, Shobha A.,Iyer, Suresh

supporting information, p. 308 - 316 (2020/10/06)

Monodentate and bidentate chelating oximes are readily available ligands for the Pd catalysis of the Mizoroki–Heck reaction and the Suzuki coupling. High yields were obtained in the Suzuki coupling in aqueous dioxane with TBABr as additive. The oximes can be easily synthesized from the corresponding ketones or aldehydes and thus provide a very large number of nitrogen-based ligands. They have the advantage of not undergoing oxidative degradation, common for phosphine ligands. Chelating oximes with Pd(OAc)2, activate aryl iodides to give high yields of the substitution products in the Mizoroki–Heck reactions as well as the Suzuki coupling. Acetophenone oxime ligand with Pd(OAc)2, catalyzed the reaction of aryl iodides with 1,2-disubstituted alkenes in moderate to high yields. As a test example, the LaRock indole annulation and synthesis of isocoumarin were achieved with acetophenone oxime ligand and Pd(OAc)2 in high yields.

Synthesis of β-hydroxy aryl selenides via transition-metal-free three-component reaction of arylamines, elemental selenium, and epoxides

Wang, Hongwei,Li, Hongchen,Bai, Yalong,Hei, Yanling,Chen, Junwei,Yu, Guoqi,Zhou, Yun-Bing

, p. 3621 - 3629 (2021/06/21)

An efficient protocol for the construction of valuable β-hydroxy aryl selenides from easily available arylamines, elemental selenium, and epoxides through a transition-metal-free radical process is described. A wide variety of β-hydroxy aryl selenides were obtained in good to excellent yields with excellent stereo- and regioselectivity. In this reaction, two C-Se bonds can be built along with the cleavage of a C-N and C-O bond, demonstrating the high step economy and efficiency of this approach.

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