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inquiryProduct Description Product website: http://www.finerchem.com Product Name 2-Phenylpropionaldehyde CAS No. 93-53-8
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Product Name: 2-PHENYLPROPIONALDEHYDE Synonyms: hydratropaaldehyde;Hydrotropic aldehyde;Propionaldehyde, 2-phenyl-;Hydratropaldehyde~2-Phenylpropanal;2-PHENYLPROPIONALDEHYDE 95+% FCC;3-Phenylpropionaldehyde,~98%;2-Phenylpropionaldehyde,97%;&alph
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Product Name: 2-PHENYLPROPIONALDEHYDE CAS: 93-53-8 MF: C9H10O MW: 134.18 EINECS: 202-255-5 Mol File: 93-53-8.mol 2-PHENYLPROPIONALDEHYDE Structure 2-PHENYLPROPIONALDEHYDE Chemical Properties Melting point 60°C Boiling poin
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inquiry(2S)-2-phenyl-1-propanamine
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With immobilised amine transaminase from the moderate halophilic bacterium Halomonas elongata; sodium pyruvate In aq. phosphate buffer; dimethyl sulfoxide at 37℃; under 760.051 Torr; for 3h; pH=8; | 90% |
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With sodium periodate; sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 4h; | 77% |
(S)-2-phenyl-1-propanol
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With Dess-Martin periodane In dichloromethane for 1.66667h; Inert atmosphere; | 74% |
With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h; Inert atmosphere; | 70% |
With Dess-Martin periodane | |
With sodium hydrogencarbonate; Dess-Martin periodane In dichloromethane Dess-Martin oxidation; Inert atmosphere; optical yield given as %ee; | |
Dess-Martin Oxidation; |
styrene
carbon monoxide
A
3-phenyl-propionaldehyde
B
ethylbenzene
C
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With hydrogen; PtCl(SnCl3)<(S,S)-BDPP> In toluene at 40℃; under 60004.8 Torr; for 55h; | A 42% B 3% C 31% |
With hydrogen; PtCl(SnCl3)<(S,S)-BDPP> In toluene at 40℃; for 55h; | A 42% B 3% C 31% |
With C44H32Cl4P2PtSn(2+); hydrogen at 40℃; under 30003 Torr; for 336h; Reagent/catalyst; Solvent; Temperature; Time; Pressure; chemoselective reaction; | A n/a B n/a C n/a |
styrene
A
3-phenyl-propionaldehyde
B
ethylbenzene
C
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With hydrogen; PtCl(SnCl3)<(S,S)-BDPP> In toluene at 40℃; under 60004.8 Torr; for 55h; | A 42% B 3% C 31% |
styrene
carbon monoxide
A
3-phenyl-propionaldehyde
B
ethylbenzene
C
(S)-2-phenyl-propionaldehyde
D
(R)-2-phenylpropanal
Conditions | Yield |
---|---|
With [(2S,3S)-2,4-bis(diphenylphosphino)pentane]Pt(SnCl3)Cl; hydrogen In toluene at 40℃; under 51714.8 Torr; for 138h; | A 68.7 % Chromat. B n/a C 25% D 6.3% |
With hydrogen; PtCl2 In toluene at 40℃; under 60004.8 Torr; for 160h; Product distribution; var. PtCl2-diphosphine 2,4-bis(diphenylphosphino)pentane (BDPP)-tin(II)fluoride catalytic system; other temp. and time; | |
With hydrogen; bis(benzonitrile)dichloroplatinum(II); tin(ll) chloride; (2S,4S)-2,4-bis[((S)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-2-yl)oxy]pentane In toluene at 100℃; under 76000 Torr; for 2h; Title compound not separated from byproducts; |
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With ozone In dichloromethane at -78℃; for 0.0833333h; | 23% |
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With ozone In dichloromethane at -78℃; for 0.0833333h; | 23% |
styrene
carbon monoxide
A
3-phenyl-propionaldehyde
B
(S)-2-phenyl-propionaldehyde
C
(R)-2-phenylpropanal
Conditions | Yield |
---|---|
With acetylacetonatodicarbonylrhodium(l); hydrogen; (R,S)-binaphos In benzene at 60℃; under 38000 Torr; for 43h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | A 12% B n/a C n/a |
With acetylacetonatodicarbonylrhodium(l); hydrogen; (R,S)-binaphos In benzene at 60℃; under 38000 Torr; for 43h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | A 8% B n/a C n/a |
With PtCl2-SnCl2 complex of (4R,5R)-2,2-dimethyl-4,5-bis(diphenylphosphinomethyl)-1,3-dioxolan and its bis(dibenzophosphole) analogue; hydrogen In benzene at 40℃; under 160341 Torr; for 36h; Product distribution; var. temp., var. pressure, var. time, var. PtCl2-SnCl2 complexes, var. ratios of H2:CO; optical purity, selectivity, branched:normal ratio; |
styrene
carbon monoxide
A
3-phenyl-propionaldehyde
B
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With (R,R)-<<(bicyclo<2.2.2>octane-2,3-diyl)bis(methylene)>bis<5H-benzophosphinindole>>PtCl2 (5a); hydrogen; tin(ll) chloride In benzene at 50℃; under 53200 - 114000 Torr; for 23h; Product distribution; other aromatic olefins; other platinum dichloride complex; | |
With Rh(acac)2(CO)2; C62H50N4O7P2; hydrogen at 40℃; under 2068.65 - 6205.94 Torr; for 4h; optical yield given as %ee; enantioselective reaction; | |
With (acetylacetonato)dicarbonylrhodium (l); C54H39NO2P2; hydrogen In toluene at 60℃; under 15001.5 Torr; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | |
With dicarbonylacetylacetonato rhodium (I); C41H50O3P2; hydrogen at 30℃; under 7500.75 Torr; for 16h; Temperature; Pressure; Time; Concentration; Autoclave; Inert atmosphere; enantioselective reaction; | A n/a B n/a |
With 2,2',2'',2'''-(1,2-phenylenebis((1S,3S)-tetrahydro-5,8-dioxo-1H-(1,2,4)diazaphospholo(1,2-a)pyridazine-2,1,3(3H)-triyl))tetrakis(N-(1S)-1-phenylethyl)-benzamide; (acetylacetonato)dicarbonylrhodium (l); hydrogen In tetrahydrofuran at 60℃; under 8517.48 Torr; for 24h; Flow reactor; enantioselective reaction; | A n/a B n/a |
styrene
carbon monoxide
A
(S)-2-phenyl-propionaldehyde
B
(R)-2-phenylpropanal
Conditions | Yield |
---|---|
With acetylacetonatodicarbonylrhodium(l); 3,5-bis<(4,4'-di-t-butyl-6,6'-dimethoxy-2,2'-biphenyl-1,1'-diyl)phosphite>-1,2-O-isopropylidene-D-xylofuranose; hydrogen In toluene at 25℃; under 6750.5 Torr; for 15h; Product distribution; var. ligands, pressures, temp., times; | |
With hydrogen; PtCl2-2,4-bis(diphenylphosphino)pentane (BDPP)-2SnCl2; tin(ll) chloride In toluene at 40℃; under 60004.8 Torr; for 160h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With hydrogen; 5)(CO)2> at 40℃; under 6750.5 Torr; for 5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With dimethylsulfide; ozone 1.) MeOH, O2, -78 deg C, 2.) -10 deg C, 1 h, RT, 1 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
2-Phenylpropanal
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With diethylzinc | |
Multi-step reaction with 2 steps 1: Na2SO4 / benzene / 20 °C 2: 1.) MeI, 2.) aq. HCl / 1.) 60 deg C, 2.) n-pentane View Scheme |
(3,3-diethoxypropyl)benzene
A
3-phenyl-propionaldehyde
B
(S)-2-phenyl-propionaldehyde
C
(R)-2-phenylpropanal
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In acetone for 5h; Heating; |
(2S,3S)-methylphenylalanine
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With indan-1,2,3-trione hydrate In water; benzene at 80℃; for 0.166667h; |
trimethylaluminum
(4R,5R)-2-((E)-Styryl)-[1,3]dioxolane-4,5-dicarboxylic acid bis-dimethylamide
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With ozone 1.) toluene, hexane, room temp.,12 h, 2.) MeOH, -78 deg C; Yield given. Multistep reaction; |
A
3-phenyl-propionaldehyde
B
(S)-2-phenyl-propionaldehyde
C
(R)-2-phenylpropanal
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In acetone for 5h; Heating; |
Conditions | Yield |
---|---|
With hydrogenchloride; methyl iodide 1.) 60 deg C, 2.) n-pentane; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride; methyl iodide 1.) 60 deg C, 2.) n-pentane; Yield given. Multistep reaction; |
1-(4-morpholino)-2-phenylpropene
A
(S)-2-phenyl-propionaldehyde
B
(R)-2-phenylpropanal
Conditions | Yield |
---|---|
With L-Tartaric acid In ethanol; water at -60℃; for 0.5h; Product distribution; variation of chiral acids, solvent, temperature; |
2-phenylpropane-1,1-diyl diacetate
A
(S)-2-phenyl-propionaldehyde
B
(R)-2-phenylpropanal
Conditions | Yield |
---|---|
With sodium hydroxide; Candida rugosa lipase In various solvent(s) for 1.16667h; Product distribution; pH=7; different substrates, enzymes, solvents and reaction times; |
2-Phenylpropanal
diethylzinc
A
(2S,3S)-erythro-2-phenylpentan-3-ol
B
(2R,3S)-threo-2-phenylpentan-3-ol
C
(2R,3R)-erythro-2-phenylpentan-3-ol
D
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With naphthalene; (R)-PDB In hexane Addition; Further byproducts given; |
(E,2R,5S)-7-methyl-5-(2,4,6-trimethylbenzenesulfonyl)amino-2-phenyloct-3-ene
A
(S)-2-phenyl-propionaldehyde
B
N-((S)-1-Formyl-3-methyl-butyl)-2,4,6-trimethyl-benzenesulfonamide
Conditions | Yield |
---|---|
Stage #1: (E,2R,5S)-7-methyl-5-(2,4,6-trimethylbenzenesulfonyl)amino-2-phenyloct-3-ene With ozone In hexane; chloroform at -78℃; ozonolysis; Stage #2: With zinc In hexane; chloroform at -78 - 0℃; for 0.166667h; Reduction; Title compound not separated from byproducts; |
(1S,2R,3S)-1,2-Dihydroxy-1,3-diphenylbutane
A
(S)-2-phenyl-propionaldehyde
B
benzaldehyde
Conditions | Yield |
---|---|
With sodium periodate In dichloromethane for 1h; Oxidation; oxidative cleavage; Title compound not separated from byproducts.; |
Conditions | Yield |
---|---|
With furanoside diphosphite derived from D-(+)-glucose; hydrogen; acetylacetonatodicarbonylrhodium(l) In toluene at 20℃; | |
Stage #1: carbon monoxide With acetylacetonatodicarbonylrhodium(l); tris[(R)-2’-(benzyloxy)-1,1’-binaphthyl-2-yl]phosphite; hydrogen In toluene at 80℃; under 22502.3 Torr; for 3h; Stage #2: styrene In toluene regioselective reaction; | |
With hydrogen; acetylacetonatodicarbonylrhodium(l); (S,S,S)-BOBPHOS In toluene at 60℃; under 7500.75 Torr; for 16h; Product distribution / selectivity; Hydroformylation Reaction; Argonaut Endeavour parallel autoclave system; | n/a |
Conditions | Yield |
---|---|
Stage #1: (E)-1,3-diphenyl-N-[(2-pyridyl)sulfonyl]prop-2-en-1-imine; dimethyl zinc(II) With copper(I) thiophene-2-carboxylate; (R,S,S)-phosphoramidite monodentate Feringa ligand In toluene at -20℃; for 2h; Stage #2: With ozone In dichloromethane at -78℃; Stage #3: With dimethylsulfide for 0.333333h; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With carbon monoxide; hydrogen; acetylacetonatodicarbonylrhodium(l); 3,4-bis[(R,R)-2,5-diphenyl-phospholan-1-yl]furan-2,5-dione In toluene at 80℃; under 7757.43 Torr; for 3h; Product distribution / selectivity; | A n/a B n/a |
With carbon monoxide; hydrogen; acetylacetonatodicarbonylrhodium(l); (R,R)-2,3-bis(2,5-diphenyl-phospholan-1-yl)-quinoxaline In toluene at 80℃; under 7757.43 Torr; for 3h; Product distribution / selectivity; | A n/a B n/a |
2-Phenylpropanal
B
(S)-formic acid 1-phenylethyl ester
C
(S)-2-phenyl-propionaldehyde
D
(R)-2-phenylpropanal
Conditions | Yield |
---|---|
With glucose-6-phosphate dehydrogenase; α-D-glucose 6-phosphate In various solvent(s) at 20℃; pH=7; Product distribution; Further Variations:; pH-values; Reagents; Temperatures; Baeyer-Villiger oxidation; | |
With phenylacetone monooxygenase from Thermobifida fusca; Tris-HCl buffer; D-glucose 6-phosphate at 27℃; pH=6; Product distribution; Further Variations:; pH-values; Baeyer-Villiger oxidation reaction; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 80 percent / Et3N; TiCl4 / CH2Cl2 / 5 h / Heating 2.1: (R,S,S)-phosphoramidite monodentate Feringa ligand; copper thiophene-2-carboxylate / toluene / 2 h / -20 °C 2.2: O3 / CH2Cl2 / -78 °C 2.3: Me2S / 0.33 h View Scheme |
trans-(2S,3R)-epoxy-1,3-diphenylpropan-1-one
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 8 percent / H2O / CH2Cl2; ethanol / 0.5 h 2: 95 percent / zinc borohydride / diethyl ether / 1 h 3: NaIO4 supported on silice gel / CH2Cl2 / 1 h View Scheme | |
Multi-step reaction with 3 steps 1: 95 percent / zinc borohydride / diethyl ether / 0.5 h 2: 93 percent / hexane / 1 h / 0 °C 3: NaIO4 supported on silice gel / CH2Cl2 / 1 h View Scheme |
(S)-2-phenyl-propionaldehyde
(S)-2-phenyl-1-propanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 0℃; for 0.5h; | 96% |
With sodium tetrahydroborate In methanol at -78 - 20℃; optical yield given as %ee; | |
With sodium tetrahydroborate In methanol at -78℃; for 1h; Inert atmosphere; | |
With sodium tetrahydroborate Inert atmosphere; optical yield given as %ee; |
phenyl(trimethylsiloxy)acetonitrile
(S)-2-phenyl-propionaldehyde
A
3-Hydroxy-2,4-diphenyl-2-(trimethylsilyl)pentannitril
B
(2R*,3S*)-1,3-Diphenyl-2-(trimethylsilyloxy)-1-butanon
C
(2S*,3S*)-1,3-Diphenyl-2-(trimethylsilyloxy)-1-butanon
Conditions | Yield |
---|---|
With lithium diisopropyl amide In diethyl ether at -78℃; for 2h; Product distribution; further solvent and time and temperature; | A 95% B n/a C n/a |
Conditions | Yield |
---|---|
With bis(cyclopentadienyl)titanium dichloride; zinc In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere; | 93% |
diazoacetic acid ethyl ester
3,3',5,5'-tetramethyl-4,4'-dimethoxy benzhydrylamine
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
Stage #1: 3,3',5,5'-tetramethyl-4,4'-dimethoxy benzhydrylamine With triphenylborane; (3S)-(+)-2,2'-diphenyl-(3,3'-biphenanthrene)-4,4'-diol In toluene at 80℃; for 0.5h; Inert atmosphere; Schlenk technique; Sealed tube; Stage #2: diazoacetic acid ethyl ester; (S)-2-phenyl-propionaldehyde In toluene at -10℃; for 24h; Molecular sieve; Inert atmosphere; Schlenk technique; stereoselective reaction; | 92% |
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With bis(trifluoromethanesulfonyl)amide In dichloromethane at -78℃; for 0.25h; Mukaiyama aldol reaction; | 84% |
Conditions | Yield |
---|---|
With phenylborondichloride; potassium carbonate In dichloromethane at 20℃; for 48h; Inert atmosphere; enantioselective reaction; | 83% |
With phenylborondichloride; potassium carbonate In dichloromethane for 3h; diastereoselective reaction; | 83% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 20℃; | 82% |
Conditions | Yield |
---|---|
With sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene In water; tert-butyl alcohol at 0 - 20℃; for 2h; | 79% |
With potassium permanganate; magnesium sulfate In acetone Inert atmosphere; |
Conditions | Yield |
---|---|
With phenylborondichloride; potassium carbonate In dichloromethane at 20℃; for 48h; Inert atmosphere; enantioselective reaction; | 78% |
With phenylborondichloride; potassium carbonate In dichloromethane for 3h; diastereoselective reaction; | 78% |
Conditions | Yield |
---|---|
With phenylborondichloride; potassium carbonate In dichloromethane for 3h; diastereoselective reaction; | 77% |
(S)-2-phenyl-propionaldehyde
(S)-2-methylpropane-2-sulfinamide
Conditions | Yield |
---|---|
With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; | 76% |
Conditions | Yield |
---|---|
With bis(trifluoromethanesulfonyl)amide In dichloromethane; toluene at -78℃; for 0.5h; Inert atmosphere; enantioselective reaction; | 75% |
Conditions | Yield |
---|---|
Stage #1: 3,3-bis(triethylsilyl) benzyl enol ether With N,N,N,N,N,N-hexamethylphosphoric triamide; tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1.5h; Inert atmosphere; Stage #2: (S)-2-phenyl-propionaldehyde In tetrahydrofuran; pentane at -78℃; for 0.166667h; Inert atmosphere; diastereoselective reaction; | 75% |
Conditions | Yield |
---|---|
With phenylborondichloride; potassium carbonate In dichloromethane for 3h; diastereoselective reaction; | 73% |
acetone tris(triethylsilyl)silyl enol ether
(S)-2-phenyl-propionaldehyde
C30H60O2Si4
Conditions | Yield |
---|---|
With bis(trifluoromethanesulfonyl)amide In dichloromethane at 0 - 20℃; Inert atmosphere; enantioselective reaction; | 72% |
(furan-2-yloxy)-trimethylsilane
4-Methoxy-2-methylsulfenylaniline
(S)-2-phenyl-propionaldehyde
C21H23NO3S
Conditions | Yield |
---|---|
Stage #1: 4-Methoxy-2-methylsulfenylaniline; (S)-2-phenyl-propionaldehyde With magnesium sulfate at 22℃; for 0.166667h; Stage #2: (furan-2-yloxy)-trimethylsilane With N-[2-PPh2-benzylidene]-L-tert-leucine (4-methoxyphenyl)amide; silver(I) acetate; isopropyl alcohol In tetrahydrofuran at -78℃; for 20h; Mannich reaction; | 68% |
Conditions | Yield |
---|---|
Stage #1: C30H60O2Si4 With lithium hexamethyldisilazane In hexane; N,N-dimethyl-formamide at -40℃; Inert atmosphere; Stage #2: (S)-2-phenyl-propionaldehyde In hexane; N,N-dimethyl-formamide at -60℃; Inert atmosphere; optical yield given as %de; enantioselective reaction; | A 66% B n/a |
tert-butyl (E)-crotonate
(S)-2-phenyl-propionaldehyde
(2R,3R,4S)-tert-butyl 3-hydroxy-2-ethyl-4-phenylpentanoate
Conditions | Yield |
---|---|
Stage #1: tert-butyl (E)-crotonate; (S)-2-phenyl-propionaldehyde; chiral Rh(Phebox) In toluene at 50℃; for 0.5h; Stage #2: With potassium fluoride; tetrabutyl ammonium fluoride; water In tetrahydrofuran; N,N-dimethyl-formamide at 50℃; for 16h; Further stages.; | 61% |
triethylaluminum
(S)-2-phenyl-propionaldehyde
(R,R)/(S,S)-2-phenylpentan-3-ol
Conditions | Yield |
---|---|
With methyllithium In diethyl ether; dichloromethane at -78℃; | 56% |
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at -60℃; for 24h; Sakurai-Hosomi Allylation; Schlenk technique; Glovebox; Inert atmosphere; | A 53% B n/a |
Conditions | Yield |
---|---|
With N,N'-((11bS,11b'S)-azanediylbis(2,6-bis(3,5-bis(perfluoropropyl)phenyl)-4λ5-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine-4-yl-4-ylidene))bis(1,1,1-trifluoromethanesulfonamide) In methyl cyclohexane at -78 - -20℃; for 48h; Reagent/catalyst; Diels-Alder Cycloaddition; Molecular sieve; diastereoselective reaction; | 48% |
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at -60℃; for 24h; Sakurai-Hosomi Allylation; Schlenk technique; Glovebox; Inert atmosphere; diastereoselective reaction; | A 47% B n/a |
2-(Z-3-chloroprop-2-enyl)-4,4,5,5-tetramethyl-1,2,3-dioxaborolane
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With (2S)-2-((2-hydroxy-3-(triphenylsilyl)benzyl)amino)-2-(3-hydroxyadamantan-1-yl) 1-(isoindolin-2-yl)ethan-1-one; zinc dimethoxide In toluene at 22℃; for 14h; Glovebox; Inert atmosphere; Sealed tube; stereoselective reaction; | 32% |
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