2,2-bis(benzyl)-1,3-dithiolane
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
With trichloroisocyanuric acid; silver nitrate In water; acetonitrile Ambient temperature; | 99% |
With (CH3)3CI; dimethyl sulfoxide for 12h; | 95% |
With trimethylsilyl iodide; dimethyl sulfoxide In tetrachloromethane at 75 - 80℃; for 6h; | 85% |
With hydrogenchloride; dihydrogen peroxide In methanol Ambient temperature; | 81% |
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20 - 25℃; for 2h; Irradiation; | 98% |
Conditions | Yield |
---|---|
With chloral hydrate In hexane at 25℃; for 5h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With copper(II) sulfate In tetrahydrofuran; methanol; water for 4h; Heating; | 95% |
1,3-Diphenylpropanone oxime O-acetate
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
Stage #1: 1,3-Diphenylpropanone oxime O-acetate With dicobalt octacarbonyl; triethylamine In diethyl ether at 20℃; for 0.25h; deoximation; Stage #2: With water In methanol at 20℃; for 0.5h; Hydrolysis; | 93% |
With diiron nonacarbonyl In methanol at 60℃; for 1h; Product distribution; Fe(CO)5, UV irradiation; | 82% |
1,3-diphenylacetone N,N-dimethylhydrazone
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioxorhenium(VII) In acetic acid; acetonitrile at 0 - 20℃; Product distribution; oxidative cleavage; | 93% |
With porcin pancreatic lipase In water; acetone at 20℃; for 96h; Hydrolysis; | 94 % Chromat. |
1,3-diphenyl-1-phenylsulfanylpropan-2-one
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
With zinc In acetic acid | 92% |
Conditions | Yield |
---|---|
With n-butyllithium at -78℃; for 8h; | 92% |
Conditions | Yield |
---|---|
With copper(II) sulfate In tetrahydrofuran; methanol; water for 19h; Heating; | 90% |
With iron pentacarbonyl In methanol for 48h; Product distribution; Irradiation; Fe2(CO)9, 60 deg C; | 81% |
With water; oxygen In acetonitrile at 60℃; under 760.051 Torr; for 6h; Autoclave; Green chemistry; | 32% |
With bismuth(lll) trifluoromethanesulfonate; bismuth(III) bromide In water; acetone; acetonitrile for 4h; Heating; | |
Multi-step reaction with 2 steps 1: acetic acid; chlorine 2: NaN3; aqueous acetic acid; CO2 View Scheme |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel(0); 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc In acetonitrile at 25℃; for 12h; Inert atmosphere; | 90% |
With bis(1,5-cyclooctadiene)nickel(0); 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc In acetonitrile at 25℃; for 12h; Schlenk technique; Inert atmosphere; | 90% |
With tetrabutylammonium tetrafluoroborate; (2,2'-bipyridine)nickel(II) dibromide In acetonitrile Ambient temperature; zinc rod as the anode, vitreous carbon gauze as the cathode, 0.1 A; | 80% |
With [2,2]bipyridinyl; tetrabutylammonium tetrafluoroborate; tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In acetonitrile at 25℃; Product distribution; Kinetics; Electrochemical reaction; | |
With bis(1,5-cyclooctadiene)nickel(0); magnesium chloride; zinc In acetonitrile at 20℃; for 12h; Inert atmosphere; | 41 mmol |
Conditions | Yield |
---|---|
With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis; | 90% |
benzyl bromide
A
phenylacetonitrile
B
1,1'-(1,2-ethanediyl)bisbenzene
C
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
add of carbon monoxide; | A 1% B 6% C 89% |
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; chloro-trimethyl-silane; nickel(II) bromide 2-methoxyethyl ether complex; zinc In tetrahydrofuran; N,N-dimethyl acetamide at 40℃; for 2h; Sealed tube; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With silica gel; cobalt(II) nitrate for 0.283333h; microwave irradiation; | 85% |
With pyridiniumchlorochromate on aluminumoxide at 20℃; for 20h; | 84% |
With boron trifluoride diethyl etherate; tetrabutylammonium periodite In acetonitrile for 4h; Heating; | 60% |
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethylsulfoxide-d6 at 23℃; primary kinetic isotope effect by its α-deuterio analog; |
Conditions | Yield |
---|---|
With lithium tert-butoxide In tetrahydrofuran at 23℃; for 3h; Glovebox; | 81% |
Conditions | Yield |
---|---|
In acetonitrile Ambient temperature; Bu4NBF4, nickel rod anode, nickel foam catode, 1.5 A/dm2; | 80% |
With diethyl ether; triethylamine | |
Multi-step reaction with 4 steps 1: 98 percent / diethyl ether 2: 93 percent / diethyl ether 3: 89 percent / SnCl4 / Ambient temperature 4: 92 percent / Zn / acetic acid View Scheme | |
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 96 h / Cooling with ice 2: 3,6-dimethyl-1,2,4,5-tetrazine / chloroform / 1 h / 20 °C View Scheme |
2,3-epoxy-1,3-diphenyl-2-phenylsulfinylpropane
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
With sodium phenylselenide In ethanol for 3h; Ambient temperature; | 80% |
With sodium phenylselenide In ethanol for 3h; Ambient temperature; | 80% |
carbon monoxide
benzyl chloride
A
1,1'-(1,2-ethanediyl)bisbenzene
B
toluene
C
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; tetrabutylammonium tetrafluoroborate; iron(II) chloride; Fe64/Ni36 anode In N,N-dimethyl-formamide Ambient temperature; electrolysis; | A 10 % Chromat. B n/a C 80% |
With [2,2]bipyridinyl; tetrabutylammonium tetrafluoroborate; iron(II) chloride; Fe64/Ni36 anode In N,N-dimethyl-formamide Product distribution; Mechanism; Ambient temperature; electrolysis, var. of electrode material, ligand, halogen, other aryl and alkyl halogenides; | A 10 % Chromat. B n/a C 90 % Chromat. |
2.2-Dibenzyl-1.3-dithian
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
With antimonypentachloride In dichloromethane at 0℃; for 0.166667h; | 78% |
With 2,4,6-triphenylpyrilium perchlorate; oxygen In acetonitrile for 5h; Irradiation; | 31% |
3,3,6,6-tetrabenzyl-1,2,4,5-tetraoxan
A
phenylacetic acid
B
benzyl 2-phenylacetate
C
1,1'-(1,2-ethanediyl)bisbenzene
D
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
In benzene at 150℃; for 72h; Product distribution; Mechanism; thermolysis; var. temp., time and solvent; | A n/a B 12% C 77% D 2% |
carbon monoxide
B
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
In toluene at 20℃; under 760.051 Torr; Inert atmosphere; Schlenk technique; | A 72% B 76% |
carbon monoxide
benzyl bromide
A
phenylacetic acid
B
benzyl 2-phenylacetate
C
1,1'-(1,2-ethanediyl)bisbenzene
D
toluene
E
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
iron pentacarbonyl; tetrabutylammonium sulfate In sodium hydroxide; benzene at 20℃; under 760 Torr; for 15h; Product distribution; variation of solvent, temperature, catalyst, pressure, reaction time and ratio of catalyst and substrate, examinations with further benzyl halides; | A 75% B 3% C 6% D 2% E 14% |
Conditions | Yield |
---|---|
add of carbon monoxide; | A 9% B 75% |
morpholine
3,3-bis(phenylmethyl)-1,2-dioxetane
A
N-<(2-benzyl-2-hydroxy-3-phenylpropyl)oxy>morpholine
B
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
In dichloromethane for 15h; | A 74% B 12% |
Conditions | Yield |
---|---|
With lithium; 4,4'-di-tert-butylbiphenyl In tetrahydrofuran for 60h; Ambient temperature; Irradiation; ultrasonic irradiation; | 73% |
Conditions | Yield |
---|---|
With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis; | 70% |
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; nickel(II) chloride hexahydrate; 4-acetoxybenzophenone; 4,4'-di-tert-butyl-2,2'-bipyridine at 35℃; for 48h; Inert atmosphere; Sealed tube; Irradiation; Schlenk technique; | 70% |
carbon monoxide
benzyl bromide
A
phenylacetic acid
B
benzyl 2-phenylacetate
C
1,1'-(1,2-ethanediyl)bisbenzene
D
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
iron pentacarbonyl; tetrabutylammonium sulfate In sodium hydroxide; dichloromethane at 20℃; under 760 Torr; for 20h; | A 69% B 7% C 3% D 20% |
iron pentacarbonyl; tetrabutylammonium sulfate In sodium hydroxide; dichloromethane at 25℃; under 45600 Torr; for 27h; | A 66% B 8% C 4% D 11% |
Conditions | Yield |
---|---|
With C41H50ClN3Pd; sodium t-butanolate In 1,4-dioxane at 100℃; for 4h; Reagent/catalyst; | 69% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol; water | 100% |
With sodium tetrahydroborate In methanol at 0℃; for 0.25h; Inert atmosphere; | 100% |
With C26H33ClN5Ru(1+)*BF4(1-); potassium tert-butylate In isopropyl alcohol for 4h; Inert atmosphere; High pressure; Reflux; | 100% |
Conditions | Yield |
---|---|
With acetic acid; acetone oxime at 135℃; for 1.5h; | 100% |
With hydroxylamine hydrochloride; glycine In N,N-dimethyl-formamide at 25℃; for 6h; | 98% |
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux; | 96% |
ethane-1,2-dithiol
1,3-Diphenylpropanone
2,2-bis(benzyl)-1,3-dithiolane
Conditions | Yield |
---|---|
Nafion-H In benzene Heating; | 100% |
With silica gel; zirconium(IV) chloride In dichloromethane for 0.5h; Ambient temperature; | 99% |
With silica gel; iron(III) chloride In dichloromethane Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With trichloroacetic acid at 100℃; for 0.0833333h; Fischer indole synthesis; | 100% |
With phosphorus trichloride In benzene | 80% |
With Amberlite IR 120 In ethanol at 80℃; for 12h; Fischer Indole Synthesis; | 80% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 110℃; for 0.25h; Fischer indole synthesis; Microwave irradiation; Sealed vessel; | 77% |
trimethyl phosphonoacetate
1,3-Diphenylpropanone
4-Phenyl-3-(phenylmethyl)-2-butenoic acid methyl ester
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In diethyl ether; hexane 1.) -20 deg C, 20 min, 2.) r.t., 50 h; | 100% |
Conditions | Yield |
---|---|
With acetic acid In methanol Heating; | 100% |
Conditions | Yield |
---|---|
at 250℃; for 0.0166667h; Fischer indole synthesis; | 100% |
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
With La(Cp)3 In tetrahydrofuran at 20℃; for 2h; Reagent/catalyst; Inert atmosphere; | 100% |
With [RhCl2(p-cymene)]2 In neat liquid at 60℃; for 15h; Inert atmosphere; Glovebox; chemoselective reaction; | |
With C23H33MnN3Si2 In diethyl ether at 25℃; for 16h; Glovebox; Inert atmosphere; chemoselective reaction; |
malononitrile
1,3-Diphenylpropanone
2-(1,3-diphenylpropan-2-ylidene)malononitrile
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid In benzene at 120℃; Knoevenagel Condensation; Dean-Stark; | 99% |
With ammonium acetate In acetic acid; benzene for 48h; Heating; | 65% |
Conditions | Yield |
---|---|
With lithium perchlorate In diethyl ether at 20℃; for 0.25h; | 99% |
Conditions | Yield |
---|---|
With C29H46LaN3Si2 at 15℃; for 4h; Inert atmosphere; Glovebox; Schlenk technique; | 99% |
With tris(2,4,6-trimethoxyphenyl)phosphine In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; | 98% |
With L-proline potassium salt at 20℃; for 24h; | 92% |
With iodine In dichloromethane at 0℃; for 0.5h; | |
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.5h; |
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol | 98.8% |
1,2-di(4-methylphenyl)-1,2-ethanedione
1,3-Diphenylpropanone
2,5-diphenyl-3,4-di(p-tolyl)cyclopenta-2,4-dien-1-one
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at -78℃; for 0.5h; | 98% |
With potassium hydroxide In ethanol for 0.25h; Heating; | 90% |
With sodium hydroxide In methanol for 2h; Aldol condensation; Reflux; | 86% |
1,3-Diphenylpropanone
benzyl α-chlorobenzyl ketone
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; tetrabutylammomium bromide; dimethyl sulfoxide In acetonitrile for 1h; | 98% |
With [bis(acetoxy)iodo]benzene; iron(III) chloride hexahydrate In acetic acid at 20℃; for 12h; Inert atmosphere; | 82% |
With tetrachloromethane; sulfuryl dichloride at 40℃; anschliessend Erhitzen auf Siedetemperatur; | |
With sulfuryl dichloride In tetrachloromethane |
n-butyl magnesium bromide
1,3-Diphenylpropanone
1-phenyl-2-(phenylmethyl)-2-hexanol
Conditions | Yield |
---|---|
With cerium(III) chloride In tetrahydrofuran at 0℃; for 0.5h; | 98% |
With cerium(III) chloride In tetrahydrofuran at 0℃; for 1h; | 93% |
With cerium(III) chloride In tetrahydrofuran 1.) 0 deg C, 2 h, 2.) 0 deg C, 0.5 h; | 82% |
In tetrahydrofuran 1.) -78 deg C, 3 h 2.) 0 deg C, 1 h; | 20% |
n-butyllithium
1,3-Diphenylpropanone
1-phenyl-2-(phenylmethyl)-2-hexanol
Conditions | Yield |
---|---|
With cerium(III) triiodide In tetrahydrofuran at -65℃; for 3h; Product distribution; various lanthanoid chlorides; | 98% |
With cerium(III) triiodide In tetrahydrofuran at -65℃; | 98% |
With cerium(III) triiodide In tetrahydrofuran; hexane at -65℃; for 3h; | 98% |
With cerium(III) chloride at -78℃; for 3h; Product distribution; other organometallics; | 96% |
With cerium(III) chloride In tetrahydrofuran at -78℃; for 1.5h; | 96% |
Methyllanthanum triflate
1,3-Diphenylpropanone
2-methyl-1,3-diphenylpropan-2-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 0.166667h; Product distribution; Mechanism; other carbonyl compounds, other times; | 98% |
1,3-Diphenylpropanone
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydroxide In methanol; isopropyl alcohol; toluene at 80℃; Inert atmosphere; | 97.7% |
ethylene glycol
1,3-Diphenylpropanone
1,3-diphenyl-2-propanone ethylene acetal
Conditions | Yield |
---|---|
With diphenylamine-terephthalaldehyde resin p-toluenesulfonate with high sulfo group content In toluene for 6h; Dean-Stark; Reflux; | 97% |
With zeolite HSZ-360 In toluene for 5h; Heating; | 95% |
With Ti(4+)-exchanged montmorillonite In toluene for 3h; Heating; | 94% |
dimethyl methane phosphonate
1,3-Diphenylpropanone
dimethyl (2-benzyl-2-hydroxy-3-phenyl)propylphosphonate
Conditions | Yield |
---|---|
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Metallation; Stage #2: 1,3-Diphenylpropanone In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Addition; | 97% |
isopropylmagnesium chloride
1,3-Diphenylpropanone
2-Benzyl-3-methyl-1-phenyl-2-butanol
Conditions | Yield |
---|---|
With neodymium(III) chloride; lithium chloride In tetrahydrofuran at 0℃; | 97% |
Stage #1: 1,3-Diphenylpropanone With lanthanium (III) chloride bis(lithium chloride) complex In tetrahydrofuran Inert atmosphere; Stage #2: isopropylmagnesium chloride In tetrahydrofuran at 0 - 25℃; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With trimethyl orthoformate at 20℃; for 2h; | 97% |
phenylmagnesium chloride
1,3-Diphenylpropanone
1,2,3-triphenyl-propan-2-ol
Conditions | Yield |
---|---|
Stage #1: 1,3-Diphenylpropanone With lanthanium (III) chloride bis(lithium chloride) complex In tetrahydrofuran Inert atmosphere; Stage #2: phenylmagnesium chloride In tetrahydrofuran at 0 - 25℃; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; toluene at 78℃; for 1.25h; | 96% |
With potassium hydroxide In ethanol Reflux; | 95% |
With potassium hydroxide In ethanol; toluene for 0.0833333h; Heating; | 94% |
Conditions | Yield |
---|---|
With Vanadium (III) chloride-(tris-tetrahydrofuran); zinc In dichloromethane for 12h; | 96% |
n-butylcerium dichloride
1,3-Diphenylpropanone
1-phenyl-2-(phenylmethyl)-2-hexanol
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 3h; | 96% |
benzyltriphenylphosphonium bromide
1,3-Diphenylpropanone
2-benzyl-1,3-diphenyl-1-propene
Conditions | Yield |
---|---|
With sodium hydride In benzene 1.) reflux, 2 h, 2.) reflux, 120 h; | 96% |
Molecule structure of 1,3-Diphenylacetone (CAS NO.102-04-5):
IUPAC Name: 1,3-Diphenylpropan-2-one
Molecular Weight: 210.27106 g/mol
Molecular Formula: C15H14O
Density: 1.069 g/cm3
Melting Point: 32-34 °C(lit.)
Boiling Point: 331 °C at 760 mmHg
Flash Point: 149.4 °C
Index of Refraction: 1.574
Molar Refractivity: 64.95 cm3
Molar Volume: 196.5 cm3
Surface Tension: 42.1 dyne/cm
Enthalpy of Vaporization: 57.36 kJ/mol
Vapour Pressure: 0.00016 mmHg at 25 °C
Storage Temp.: 2-8 °C
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
XLogP3-AA: 3.1
H-Bond Acceptor: 1
Rotatable Bond Count: 4
Tautomer Count: 2
Exact Mass: 210.104465
MonoIsotopic Mass: 210.104465
Topological Polar Surface Area: 17.1
Heavy Atom Count: 16
Canonical SMILES: C1=CC=C(C=C1)CC(=O)CC2=CC=CC=C2
InChI: InChI=1S/C15H14O/c16-15(11-13-7-3-1-4-8-13)12-14-9-5-2-6-10-14/h1-10H,11-12H2
InChIKey: YFKBXYGUSOXJGS-UHFFFAOYSA-N
EINECS: 203-000-0
Product Categories: Aromatic Ketones (substituted)
1,3-Diphenylacetone (CAS NO.102-04-5) is frequently used in an aldol condensation reaction with benzil (a dicarbonyl) and base to create tetraphenylcyclopentadienone.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | oral | > 2gm/kg (2000mg/kg) | BEHAVIORAL: ATAXIA | National Technical Information Service. Vol. OTS0559576, |
Safety Statements: 24/25-22
S24/25:Avoid contact with skin and eyes.
S22:Do not breathe dust.
WGK Germany: 3
RTECS: EC2030000
1,3-Diphenylacetone (CAS NO.102-04-5) is also named as 1,3-Diphenyl-2-propanone ; 1,3-Diphenylpropanone ; 2-Propanone, 1,3-diphenyl- ; AI3-05001 ; Benzyl ketone ; Dibenzyl ketone ; FEMA No. 2397 ; NSC 220312 ; alpha,alpha'-Diphenylacetone . 1,3-Diphenylacetone (CAS NO.102-04-5) is light yellow solid.
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