Product Name

  • Name

    TRANS-STILBENE OXIDE

  • EINECS 215-877-7
  • CAS No. 1439-07-2
  • Article Data895
  • CAS DataBase
  • Density 1.136 g/cm3
  • Solubility
  • Melting Point 65-67 °C(lit.)
  • Formula C14H12O
  • Boiling Point 304.5 °C at 760 mmHg
  • Molecular Weight 196.249
  • Flash Point 133.4 °C
  • Transport Information
  • Appearance white to light yellow crystal powder
  • Safety 22-24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 1439-07-2 (TRANS-STILBENE OXIDE)
  • Hazard Symbols FlammableF
  • Synonyms Bibenzyl, a,a'-epoxy-, trans- (8CI);Oxirane, 2,3-diphenyl-,trans-;(2R,3R)-rel-2,3-Diphenyloxirane;(E)-Stilbene epoxide;(?à)-trans-2,3-Diphenyloxirane;(?à)-trans-Stilbene oxide;NSC100317;NSC 40295;rel-(2R,3R)-2,3-Diphenyloxirane;trans-(?à)-2,3-Diphenyloxirane;trans-1,2-Diphenylethylene oxide;trans-2,3-Diphenyloxirane;trans-Diphenyl-1,2-epoxyethane;trans-Stilbene epoxide;trans-Stilbene oxide;trans-a,a'-Epoxybibenzyl;
  • PSA 12.53000
  • LogP 3.49920

Synthetic route

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

(E)-1,2-diphenyl-ethene

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid; iron(III) perchlorate In acetonitrile at -10℃; for 0.0833333h;100%
With sodium periodate; 5-Nitro-1,10-phenanthroline; iron(II) sulfate In dichloromethane; water at 20℃; for 20h;100%
With (5,10,15,20-tetrakis(p-methoxyphenyl)-21H,23H-porphyrinate)cobalt(II); oxygen; isobutyraldehyde In acetonitrile for 3h; Ambient temperature;100%
cis-stilben
645-49-8

cis-stilben

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With sodium chlorite; edetate disodium In water; acetonitrile at 55 - 65℃; for 14h;100%
With urea hydrogen peroxide adduct; ruthenium(2,2',6':2''-terpyridine)(2,6-pyridinedicarboxylate) In tert-Amyl alcohol at 20℃; for 1h; Product distribution; Further Variations:; Catalysts; Reagents;99%
With Oxone; ethylenediaminetetraacetic acid; sodium carbonate In water; acetonitrile at 0 - 20℃; for 6h;98%
benzaldehyde
100-52-7

benzaldehyde

dimethyl<(phenyl)trimethylsilylmehyl>sulfoniumtrifluoromethanesulfonate
119547-76-1

dimethyl<(phenyl)trimethylsilylmehyl>sulfoniumtrifluoromethanesulfonate

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With cesium fluoride In 1,2-dimethoxyethane at 45℃; for 18h;98%
benzaldehyde
100-52-7

benzaldehyde

sodium (E)-2-benzylidene-1-tosylhydrazin-1-ide

sodium (E)-2-benzylidene-1-tosylhydrazin-1-ide

A

cis-1,2-diphenyloxirane
1689-71-0

cis-1,2-diphenyloxirane

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With thiophene; N-benzyl-N,N,N-triethylammonium chloride; dirhodium tetraacetate In acetonitrile at 40℃; for 24h;A n/a
B 98%
phenyldiazomethane
908094-04-2

phenyldiazomethane

benzaldehyde
100-52-7

benzaldehyde

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With hydrotris(3,4,5-tribromopyrazolyl)borate Cu (NCMe); dimethylsulfide In dichloromethane; toluene at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; diastereoselective reaction;95%
With copper acetylacetonate; ethyl isopropyl sulfide In dichloromethane73%
sodium 2-benzylidene-1-tosylhydrazin-1-ide
27992-27-4, 40154-38-9

sodium 2-benzylidene-1-tosylhydrazin-1-ide

benzaldehyde
100-52-7

benzaldehyde

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With thiophene; dirhodium tetraacetate; N-benzyl-N,N,N-triethylammonium chloride In acetonitrile at 40℃; for 3h;95%
cis-stilben
645-49-8

cis-stilben

A

cis-1,2-diphenyloxirane
1689-71-0

cis-1,2-diphenyloxirane

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With 1H-imidazole; chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III); dihydrogen peroxide In dichloromethane; acetonitrile for 2h; Ambient temperature;A 94%
B 3%
With 1H-imidazole; manganese(III) meso-tetraphenylporphyrin acetate; tetrabutylammonium periodite In dichloromethane; tert-butyl alcohol at 22℃; for 5h; Inert atmosphere;A 92%
B 3%
With oxygen In water at 25℃; under 760.051 Torr; for 4h;A n/a
B 92%
cis-stilben
645-49-8

cis-stilben

A

phenyl benzyl ketone
451-40-1

phenyl benzyl ketone

B

cis-1,2-diphenyloxirane
1689-71-0

cis-1,2-diphenyloxirane

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With 1H-imidazole; dihydrogen peroxide; Mn(TDCPP)Cl In dichloromethane; acetonitrile for 0.25h; Ambient temperature;A 2%
B 92%
C 2%
With tert.-butylhydroperoxide In water; acetonitrile at 85℃; for 24h; Catalytic behavior;A 7.2 %Chromat.
B 42.3%
C 8.3%
With O(3P) prepared by O2 discharge at 0℃; for 0.5h;A 29%
B 31%
C 40%
(E)-1,2-diphenyl-ethene
103-30-0

(E)-1,2-diphenyl-ethene

A

benzaldehyde
100-52-7

benzaldehyde

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; ruthenium(2,2',6':2''-terpyridine)(2,6-pyridinedicarboxylate) In dichloromethane for 72h; Ambient temperature;A n/a
B 92%
With oxygen; isobutyraldehyde; 4 In water; 1,2-dichloro-ethane at 40℃; for 72h;A 15%
B 83%
With pyridine N-oxide; oxochromium(V) complex of tetramethylsalen IIb In acetonitrileA 10%
B 81%
stilbene
588-59-0

stilbene

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃;91%
With Perbenzoic acid; chloroform
With 3-chloro-benzenecarboperoxoic acid
1-benzyl-3-methylbenzotriazolium iodide
1334478-48-6

1-benzyl-3-methylbenzotriazolium iodide

benzaldehyde
100-52-7

benzaldehyde

A

2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-phenylethan-1-ol

2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-phenylethan-1-ol

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide; tert-butyl alcohol at 20℃; optical yield given as %de; diastereoselective reaction;A 90%
B 70%
benzaldehyde
100-52-7

benzaldehyde

sodium (E)-2-benzylidene-1-tosylhydrazin-1-ide

sodium (E)-2-benzylidene-1-tosylhydrazin-1-ide

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With triphenyl-arsane; N-benzyl-N,N,N-triethylammonium chloride; dirhodium tetraacetate In acetonitrile at 40℃;89%
benzyl bromide
100-39-0

benzyl bromide

benzaldehyde
100-52-7

benzaldehyde

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With dimethyl sulfoxide; sodium hydroxide at 20℃; for 4h; Reagent/catalyst;89%
With (1R,2R,4R)-(+)-isobornyl methyl sulfide; sodium hydroxide In acetonitrile for 72h;50%
cyclic sulfate of meso-hydrobenzoin
89366-17-6

cyclic sulfate of meso-hydrobenzoin

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 1h;86%
(E)-1,2-diphenyl-ethene
103-30-0

(E)-1,2-diphenyl-ethene

A

cis-1,2-diphenyloxirane
1689-71-0

cis-1,2-diphenyloxirane

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With dihydrogen peroxide; iron(III) perchlorate In acetonitrile Product distribution; Heating; other oxidant, other catalysts;A 85%
B 15%
With 2MnIVTPP; 5,15,10,20-tetraphenylporphyrin In chlorobenzene at 25℃;A n/a
B 37%
With pyridine; sodium hypochlorite; benzyldimethyltetradecylammonium chloride; [MnIII(TPP)(OAc)] In dichloromethane; water for 5h; Ambient temperature; Yields of byproduct given;A n/a
B 20%
(1S,2R)-1,2-diphenylethane-1,2-diol
579-43-1

(1S,2R)-1,2-diphenylethane-1,2-diol

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With trifluoromethylsulfonic anhydride; polymer-supported triphenylphosphine oxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;85%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;85%
With diethoxyltriphenylphosphorane In toluene at 100℃; for 18h;
benzyl bromide
100-39-0

benzyl bromide

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With dimethyl sulfoxide; sodium hydroxide at 20℃; for 12h; Reagent/catalyst;85%
With dimethyl sulfoxide; silver(l) oxide at 20℃; Inert atmosphere;48%
Multi-step reaction with 3 steps
1: 1.) n-butyllithium / 1.) ether, -20 deg C, 1 h., 2.) ether
2: 100 percent / benzene / 0 °C
3: 80 percent / flame-dried cesium fluoride / 1,2-dimethoxy-ethane / 12 h / 40 °C
View Scheme
benzyldiethylsulfonium bromide

benzyldiethylsulfonium bromide

benzaldehyde
100-52-7

benzaldehyde

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
In acetonitrile at 22℃; Corey-Chaikovsky reaction; Electrolysis;83%
benzaldehyde
100-52-7

benzaldehyde

methyl (phenylmethyl)<(trimethylsilyl)methyl>sulfonium trifluoromethanesulfonate
119547-81-8

methyl (phenylmethyl)<(trimethylsilyl)methyl>sulfonium trifluoromethanesulfonate

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With cesium fluoride In 1,2-dimethoxyethane at 40℃; for 12h;80%
(1S,2R)-1,2-diphenylethane-1,2-diol
579-43-1

(1S,2R)-1,2-diphenylethane-1,2-diol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

trans-hydrobenzoin tosylate

trans-hydrobenzoin tosylate

Conditions
ConditionsYield
With triethylamine; di(n-butyl)tin oxide In dichloromethane at 20℃; for 0.666667h;A 5%
B 80%
With di(n-butyl)tin oxide; triethylamine In dichloromethane at 20℃; for 0.666667h; Tosylation;
1-benzyltetrahydro-1H-thiophen-1-ium bromide
41570-67-6

1-benzyltetrahydro-1H-thiophen-1-ium bromide

benzyl alcohol
100-51-6

benzyl alcohol

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With barium manganate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 60℃; for 1h; Corey-Tschaikosky Epoxidation;78%
Stage #1: benzyl alcohol With manganese(IV) oxide In chloroform for 2h; Reflux;
Stage #2: 1-benzyltetrahydro-1H-thiophen-1-ium bromide With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In chloroform for 0.333333h;
68%
cis-stilben
645-49-8

cis-stilben

A

benzaldehyde
100-52-7

benzaldehyde

B

cis-1,2-diphenyloxirane
1689-71-0

cis-1,2-diphenyloxirane

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With meso-tetrakis(pentafluorophenyl)porphirinato Fe(IV) nitrate; dihydrogen peroxide In dichloromethane; acetonitrile at 20℃; for 0.166667h; Product distribution; Further Variations:; Reagents; Epoxidation; Oxidation;A 3%
B 74%
C 3%
With Ni(N-(2-pyridylmethyl)-N’-(2-hydroxyethyl)ethylenediamine)(N3)2; 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetonitrile at 20℃; for 0.166667h;A 16.1%
B 6.8%
C 64.6%
With iodosylbenzene; tetraphenylporphyrine aluminum chloride In toluene for 24h; Ambient temperature;A 0.0008 mmol
B 62%
C 0.005 mmol
(+/-)-trans-5,6-diphenyl-1,4-dioxane-2,3-dione
74888-53-2, 74888-54-3

(+/-)-trans-5,6-diphenyl-1,4-dioxane-2,3-dione

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
In acetonitrile for 0.5h; Irradiation;73%
C18H20Cl2O
131423-70-6

C18H20Cl2O

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 25℃; for 0.75h;70%
trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With sodium hydroxide; methanesulfonyl chloride; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane for 0.5h; Heating;70%
benzaldehyde
100-52-7

benzaldehyde

C28H28As(1+)*BF4(1-)

C28H28As(1+)*BF4(1-)

A

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

(E)-1,2-diphenyl-ethene

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With phenyllithiumA 7%
B 66%
benzaldehyde
100-52-7

benzaldehyde

benzylmethyl <(1S,2S,3R)-3-pinanyl>sulfonium perchlorate

benzylmethyl <(1S,2S,3R)-3-pinanyl>sulfonium perchlorate

A

cis-1,2-diphenyloxirane
1689-71-0

cis-1,2-diphenyloxirane

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With sodium hydroxide; Aliquat 336 In dichloromethane at 0℃; for 24h; Product distribution; other sulfonium salts and aldehydes; also without phase transfer catalyst;A 6%
B 66%
1,3-dibenzylbenzotriazolium iodide

1,3-dibenzylbenzotriazolium iodide

benzaldehyde
100-52-7

benzaldehyde

2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,2-diphenylethanol

2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,2-diphenylethanol

2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,2-diphenylethanol

2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,2-diphenylethanol

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide; tert-butyl alcohol at 20℃; optical yield given as %de; diastereoselective reaction;A n/a
B n/a
C 66%
(E)-1,2-diphenyl-ethene
103-30-0

(E)-1,2-diphenyl-ethene

A

benzaldehyde
100-52-7

benzaldehyde

B

cis-1,2-diphenyloxirane
1689-71-0

cis-1,2-diphenyloxirane

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With Ni(N-(2-pyridylmethyl)-N’-(2-hydroxyethyl)ethylenediamine)(N3)2; 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetonitrile at 20℃; for 0.166667h;A 17.8%
B 9.4%
C 64.5%
With iodosylbenzene; tetraphenylporphyrine aluminum chloride In toluene for 24h; Ambient temperature;A 0.002 mmol
B 0.003 mmol
C 6.4%
With tert.-butylhydroperoxide; molecular sieve In Petroleum ether for 24h; Ambient temperature;A 0.27 % Spectr.
B 0.18 % Spectr.
C 9.35 % Spectr.
With Ru(VI)(octaethylporphyrin)(O)2 In dichloromethane for 24h; Yield given. Yields of byproduct given;
With iodoxybenzene; bis(acetylacetonato) oxovanadium(IV) In benzene for 4h; Product distribution;A 38 % Chromat.
B 10 % Chromat.
C 13 % Chromat.
(E)-1,2-diphenyl-ethene
103-30-0

(E)-1,2-diphenyl-ethene

A

styrene oxide
96-09-3

styrene oxide

B

benzoic acid
65-85-0

benzoic acid

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Conditions
ConditionsYield
With tetrachloromethane; 18-crown-6 ether In acetonitrile at 10℃;A 11%
B 11%
C 62%
sodium methylate
124-41-4

sodium methylate

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

erythro-2-methoxy-1,2-diphenylethanol
6941-71-5

erythro-2-methoxy-1,2-diphenylethanol

Conditions
ConditionsYield
In methanol for 108h; Heating;100%
trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

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

(E)-1,2-diphenyl-ethene

Conditions
ConditionsYield
With <(n-C4H9)3SnAl(C2H5)3>(1-)*Li(1+) In tetrahydrofuran; hexane at 25℃; for 24h; Product distribution; (C6H5)(CH3)2SiAl(C2H5)2 as deoxygenation reagent;100%
With vanadium monochloride In tetrahydrofuran at 25℃; for 12h; Inert atmosphere;100%
With n-Bu3Sn-AlMe3Li In tetrahydrofuran; hexane at 25℃; for 3h;98%
(1S,2R)-(+)-ephedrine
321-98-2

(1S,2R)-(+)-ephedrine

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

(1S,2R)-2-[(2-Hydroxy-1,2-diphenyl-ethyl)-methyl-amino]-1-phenyl-propan-1-ol

(1S,2R)-2-[(2-Hydroxy-1,2-diphenyl-ethyl)-methyl-amino]-1-phenyl-propan-1-ol

Conditions
ConditionsYield
With lithium bromide at 150℃; for 4h;100%
piperidine
110-89-4

piperidine

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

1,2-diphenyl-2-(piperidin-1-yl)ethanol
78792-49-1

1,2-diphenyl-2-(piperidin-1-yl)ethanol

Conditions
ConditionsYield
bismuth(lll) trifluoromethanesulfonate at 160℃; for 0.25h; microwave irradiation;100%
trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

Diphenylacetaldehyde
947-91-1

Diphenylacetaldehyde

Conditions
ConditionsYield
With erbium(III) triflate In dichloromethane at 20℃; for 0.75h;99%
With trimethylaluminum; 1,3-bis(3-t-butyl-5-methylsalicyl)benzene In dichloromethane Ambient temperature;98%
With copper(II) tetrafluoroborate hydrate In dichloromethane for 1.5h; Meinwald rearrangement; Reflux; regioselective reaction;95%
trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

1,2-Diphenylethanol
5773-56-8, 614-29-9

1,2-Diphenylethanol

Conditions
ConditionsYield
With formic acid; triethylamine; Pd0-EnCatTM In ethyl acetate at 23℃; for 5h;99%
With ammonium formate In ethyl acetate at 25℃; for 24h; Inert atmosphere;99%
With hydrogen; Pd/magnetite In ethyl acetate at 23℃; under 760.051 Torr; for 0.5h;94%
ethanolamine
141-43-5

ethanolamine

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

2-(2-hydroxyethylamino)-1,2-diphenylethanol

2-(2-hydroxyethylamino)-1,2-diphenylethanol

Conditions
ConditionsYield
at 90℃; for 3h;99%
cyclohexylamine
108-91-8

cyclohexylamine

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

2-(cyclohexylamino)-1,2-diphenylethanol
212394-42-8

2-(cyclohexylamino)-1,2-diphenylethanol

Conditions
ConditionsYield
bismuth(lll) trifluoromethanesulfonate at 160℃; for 0.25h; microwave irradiation;99%
Conditions
ConditionsYield
With Dowex-50WX8-supported thiourea for 0.0166667h; Microwave irradiation; neat (no solvent);98%
With ammonium chloride; thiourea at 60 - 70℃; for 0.75h; neat (no solvent);96%
With thiourea In methanol for 0.3h; Molecular sieve; Reflux;95%
With indium(III) bromide; potassium thioacyanate In acetonitrile at 60℃; for 3h;93%
With ammonium thiocyanate at 60℃; for 2h; Neat (no solvent);90%
carbon dioxide
124-38-9

carbon dioxide

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

(4R,5R)-4,5-diphenyl-1,3-dioxolan-2-one
19456-17-8, 27797-53-1, 28521-60-0, 68114-27-2

(4R,5R)-4,5-diphenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
With [La{N(SiHMe2)2}2{k3-2,2-bis(3,5-dimethylpyrazol-1-yl)-1,1-diphenylethylcyclopentadienyl}]; tetrabutylammomium bromide In neat (no solvent) at 90℃; under 7500.75 Torr; for 18h;98%
With C30H41Al2N5S; tetrabutylammomium bromide In neat (no solvent) at 90℃; under 7500.75 Torr; for 16h; stereoselective reaction;93%
With C30H34BrCrN2O4; tetrabutylammomium bromide In neat (no solvent) at 80℃; under 7500.75 Torr; for 24h; Temperature;89%
trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2,2-diphenylacetaldehyde dimethyl acetal
51936-06-2

2,2-diphenylacetaldehyde dimethyl acetal

Conditions
ConditionsYield
With mesoporous aluminosilicate catalyst, Si/Al ratio = 14:1 In chloroform at 20 - 55℃;98%
aniline
62-53-3

aniline

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

C14H12O

C14H12O

1,2-diphenyl-2-anilinoethanol

1,2-diphenyl-2-anilinoethanol

Conditions
ConditionsYield
With (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino chromium(III) chloride at 20℃; for 4h; Ionic liquid; Inert atmosphere; optical yield given as %ee; enantioselective reaction;A n/a
B 98%
allyltributylstanane
24850-33-7

allyltributylstanane

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

rel-(1R,2R)-1,2-diphenylpent-4-en-1-ol

rel-(1R,2R)-1,2-diphenylpent-4-en-1-ol

Conditions
ConditionsYield
ytterbium(III) triflate In tetrahydrofuran at 60℃; for 22h;96%
2,6-dimethylphenyl isonitrile
119072-54-7, 2769-71-3

2,6-dimethylphenyl isonitrile

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

3-(2,6-dimethylphenylamino)-2-(2,6-dimethylphenylimino)-4,5-diphenyl-2,5-dihydrofuran

3-(2,6-dimethylphenylamino)-2-(2,6-dimethylphenylimino)-4,5-diphenyl-2,5-dihydrofuran

Conditions
ConditionsYield
With gallium(III) trichloride In diethyl ether; dichloromethane at 40℃; for 2h;96%
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

2,2-diphenylacetaldehyde diethyl acetal
67820-48-8

2,2-diphenylacetaldehyde diethyl acetal

Conditions
ConditionsYield
With mesoporous aluminosilicate catalyst, Si/Al ratio = 14:1 In chloroform at 20 - 55℃;96%
trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

cis-stilben
645-49-8

cis-stilben

Conditions
ConditionsYield
With Amberlyst 15; sodium iodide In acetone at 20℃; for 3h; deoxygenation;95%
With lithium; di-o-anisylphosphinyl chloride; methyl iodide 1.) THF, 4.5 h, 2.) THF, RT; 1 h; Yield given. Multistep reaction;
Multi-step reaction with 3 steps
1: NaH / acetonitrile / 24 h / 20 °C
2: Oxone / methanol; H2O / 24 h / 20 °C
3: KOH; tetrabutylammonium bromide / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 1.) n-BuLi / 1.) THF, room t., 2.) THF, room t.
2: t-BuOK / CD3CN / -10 °C
View Scheme
Multi-step reaction with 3 steps
1: 75 percent / KOH / propan-1-ol / 8 h / Heating
2: 75 percent / m-chloroperoxybenzoic acid / CH2Cl2
3: 51 percent / N-chlorosuccinimide / benzene / 1 h / Heating
View Scheme
lithium diphenylphosphide
65567-06-8, 4541-02-0

lithium diphenylphosphide

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

(1RS,2SR)-1,2-diphenyl-2-diphenylphosphinoylmethan-1-ol
88652-80-6, 88652-81-7, 101896-50-8, 103786-11-4, 103786-12-5

(1RS,2SR)-1,2-diphenyl-2-diphenylphosphinoylmethan-1-ol

Conditions
ConditionsYield
In tetrahydrofuran93%
trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

(±)-trans-2-bromo-1,2-diphenylethan-1-ol
10368-43-1

(±)-trans-2-bromo-1,2-diphenylethan-1-ol

Conditions
ConditionsYield
With magnesium bromide In diethyl ether at 0℃; for 4h;92%
With diethyl ether; hydrogen bromide
2-Mercaptopyridine
2637-34-5

2-Mercaptopyridine

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

(S*,R*)-2-<(2-hydroxy-1,2-diphenylethyl)thio>pyridine

(S*,R*)-2-<(2-hydroxy-1,2-diphenylethyl)thio>pyridine

Conditions
ConditionsYield
With triethylamine In methanol for 18h; 0 deg C to r.t.;92%
2-buten-4-olide
497-23-4

2-buten-4-olide

trans-Stilbene oxide
1439-07-2

trans-Stilbene oxide

2,4-Diphenyl-3,7-dioxabicyclo<3.3.0>octan-8-one
72510-99-7, 90582-00-6

2,4-Diphenyl-3,7-dioxabicyclo<3.3.0>octan-8-one

Conditions
ConditionsYield
With naphthalene-1,4-dicarbonitrile In acetonitrile Irradiation;92%
With naphthalene-1,4-dicarbonitrile In acetonitrile Irradiation;90%

trans-Stilbene oxide Specification

The trans-Stilbene oxide, with the CAS registry number 1439-07-2, is also called trans-α,α'-Epoxybibenzyl. It is a kind of white to light yellow crystal powder, and belongs to the following product categories: Chiral; Oxiranes; Simple 3-Membered Ring Compounds. And the molecular formula of the chemical is C14H12O.

The characteristics of this chemical are as followings: (1)ACD/LogP: 3.39; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.39; (4)ACD/LogD (pH 7.4): 3.39; (5)ACD/BCF (pH 5.5): 220.53; (6)ACD/BCF (pH 7.4): 220.53; (7)ACD/KOC (pH 5.5): 1656.03; (8)ACD/KOC (pH 7.4): 1656.03; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 12.53 Å2; (13)Index of Refraction: 1.608; (14)Molar Refractivity: 59.71 cm3; (15)Molar Volume: 172.6 cm3; (16)Polarizability: 23.67×10-24cm3; (17)Surface Tension: 46.7 dyne/cm; (18)Density: 1.136 g/cm3; (19)Flash Point: 133.4 °C; (20)Enthalpy of Vaporization: 52.31 kJ/mol; (21)Boiling Point: 304.5 °C at 760 mmHg; (22)Vapour Pressure: 0.00157 mmHg at 25°C.

You should be cautious while dealing with this chemical. It is a kind of flammable chemical, and irritates to eyes, respiratory system and skin. Therefore, you should not breathe dust and then try to avoid contacting with skin and eyes.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O2C(c1ccccc1)C2c3ccccc3
(2)InChI: InChI=1/C14H12O/c1-3-7-11(8-4-1)13-14(15-13)12-9-5-2-6-10-12/h1-10,13-14H
(3)InChIKey: ARCJQKUWGAZPFX-UHFFFAOYAV

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