Conditions | Yield |
---|---|
With C36H54IrNP(1+)*C32H12BF24(1-) In tetrahydrofuran at 23 - 100℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; | 99% |
With rhenium(I) pentacarbonyl bromide In monoethylene glycol diethyl ether at 80℃; for 1h; Meinwald Rearrangement; Inert atmosphere; chemoselective reaction; | 93% |
With indium(III) chloride In tetrahydrofuran at 25℃; for 0.25h; Rearrangement; | 90% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With diethylzinc; trifluoroacetic acid In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; | 99% |
1,2-diphenyl-1,2-ethanediol
Diphenylacetaldehyde
Conditions | Yield |
---|---|
With KSF clay Irradiation; microwave irradiation; | 98% |
With poly(3,4-ethylenedioxythiophene) In toluene Reflux; Inert atmosphere; | 88% |
With USY-6 molecular sieve In toluene at 110℃; for 5h; Pinacol Rearrangement; | 88.6% |
1,2-diphenyl-2-methoxyethanol
Diphenylacetaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride; trifluoroacetic acid at 70℃; for 0.666667h; | 98% |
Conditions | Yield |
---|---|
With gold(III) chloride; silver hexafluoroantimonate In 1,4-dioxane at 20℃; for 0.0833333h; regioselective reaction; | 98% |
With methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide) In dichloromethane at -20℃; for 0.3h; | 95% |
copper(I) tetrafluoroborate In dichloromethane for 1.5h; Meinwald rearrangement reaction; Heating; | 95% |
With bismuth(lll) trifluoromethanesulfonate at 20℃; for 0.0833333h; Reagent/catalyst; Time; Schlenk technique; Sonication; Ionic liquid; Green chemistry; regioselective reaction; | 80% |
With mesoporous silica-supported Er(III) catalyst In toluene at 100℃; for 4h; |
Conditions | Yield |
---|---|
With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran for 1h; Ambient temperature; | 98% |
Diphenylacetaldehyde
Conditions | Yield |
---|---|
With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran for 1h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
cyclopentadienyldicarbonyl(tetrahydrofuran)iron(II) tetrafluoroborate In dichloromethane-d2 for 3h; Isomerization; | 98% |
With <(η5-C5H5)Fe(CO)2(THF)>+- In dichloromethane for 3h; Ambient temperature; | 93% |
With bismuth oxide perchlorate In dichloromethane at 20℃; for 0.416667h; Rearrangement; | 90% |
Conditions | Yield |
---|---|
With gold(III) chloride; silver hexafluoroantimonate In 1,4-dioxane at 20℃; for 0.0833333h; regioselective reaction; | A 11 %Spectr. B 98% |
With (5,10,15,20-tetraphenylporphyrinato-κ4N)(trifluoromethylsulfonate)iron(III) In 1,2-dichloro-ethane at 83℃; for 1h; Inert atmosphere; | A 23% B 73% |
With bismuth(lll) trifluoromethanesulfonate In dichloromethane for 0.5h; | A n/a B 92 % Spectr. |
Conditions | Yield |
---|---|
With 9-borabicyclo[3.3.1]nonane dimer; lithium dihydrido borata-bicyclo[3.3.0]nonane In tetrahydrofuran for 6h; Ambient temperature; | 96% |
With thexylchloroborane-Me2SO4 In dichloromethane for 0.25h; Ambient temperature; | 91% |
With thexylbromoborane dimethyl sulfide complex In carbon disulfide; dichloromethane at -20 - 20℃; for 1h; | 89% |
2,3-diphenyloxirane
Diphenylacetaldehyde
Conditions | Yield |
---|---|
methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide) In dichloromethane at -20℃; for 0.3h; | 95% |
With [5,10,15,20-tetraphenylporphinato]ytterbium(III) triflate In α,α,α-trifluorotoluene at 102℃; for 3h; Inert atmosphere; regioselective reaction; | 91% |
In hexane Ambient temperature; rearrangement on immobilized monomethylaluminum bis(4-bromo-2,6-diphenylphenoxide) column; | 72% |
Diphenylacetaldehyde
Conditions | Yield |
---|---|
With sodium carbonate In water | 95% |
Diphenylacetaldehyde
Conditions | Yield |
---|---|
With Cr-pillared montmorillonite In tetrahydrofuran for 4h; Time; Reflux; regioselective reaction; | 92% |
With rhenium(I) pentacarbonyl bromide In monoethylene glycol diethyl ether at 80℃; for 5h; Reagent/catalyst; Solvent; Temperature; Time; Meinwald Rearrangement; Inert atmosphere; | 72% |
Conditions | Yield |
---|---|
In chloroform for 1h; | 91% |
With scandium tris(trifluoromethanesulfonate) In toluene at -20℃; for 0.166667h; Inert atmosphere; | 79% |
Conditions | Yield |
---|---|
With polymer(resin Amberlyst A-26)-supported tetracarbonylhydridoferrate anion In tetrahydrofuran for 1h; Heating; | 90% |
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) In benzene for 0.166667h; Ambient temperature; | 75% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; cadmium(II) chloride In acetonitrile at -5℃; for 0.05h; | |
Multi-step reaction with 2 steps 1: triethylsilane; triethylamine / tetrahydrofuran / 1 h / 20 °C 2: triethylsilane / tetrahydrofuran / 1 h View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride In acetic acid for 0.166667h; Heating; | 90% |
Conditions | Yield |
---|---|
With phenylsilane; cobalt(II) diacetate tetrahydrate; sodium triethylborohydride In 1,2-dimethoxyethane; toluene at 25℃; for 15h; Inert atmosphere; Schlenk technique; | 90% |
Diphenylacetaldehyde
Conditions | Yield |
---|---|
With sodium carbonate In water | 89% |
Conditions | Yield |
---|---|
With nanoporous aluminosilicate (Al-13-(3.18)) at 40℃; for 3h; Reagent/catalyst; Meinwald Rearrangement; | A n/a B 88% |
With bismuth(lll) trifluoromethanesulfonate In dichloromethane for 0.333333h; | A n/a B 92 % Spectr. |
1,1,3,3-Tetramethyldisiloxane
2,2-diphenylacetic acid
Diphenylacetaldehyde
Conditions | Yield |
---|---|
Stage #1: 1,1,3,3-Tetramethyldisiloxane; 2,2-diphenylacetic acid With C24H23ClCrIrNO3; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at 40℃; for 15h; Schlenk technique; Glovebox; Inert atmosphere; Stage #2: With water In dichloromethane at 25℃; for 1h; | 88% |
(2-ethoxyethene-1,1-diyl)dibenzene
Diphenylacetaldehyde
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; for 1h; | 85% |
With hydrogenchloride; acetic acid |
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; 1,1,3,3-Tetramethyldisiloxane In toluene at 20℃; for 48h; Inert atmosphere; | 85% |
2-(2,2-Diphenyl-vinyl)-1,1,3,3-tetramethyl-2,3-dihydro-1H-benzo[1,2,5]azadisilole
Diphenylacetaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride | 84% |
2,3-diphenyloxirane
A
Diphenylacetaldehyde
B
(E)-1,2-diphenyl-ethene
Conditions | Yield |
---|---|
With molybdenum hexacarbonyl In benzene for 3h; Heating; | A 14% B 84% |
With molybdenum hexacarbonyl In 1,2-dimethoxyethane Heating; | A 66% B 28% |
Conditions | Yield |
---|---|
Stage #1: 1,1-Diphenylethylene for 0.05h; Inert atmosphere; Stage #2: With tert.-butylhydroperoxide at 102℃; for 6h; Inert atmosphere; | 80% |
With chloropyridinecobaloxime(III); water; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 24h; Wacker Oxidation; Inert atmosphere; Schlenk technique; Irradiation; | 68% |
With Perbenzoic acid; chloroform at 0 - 5℃; |
Conditions | Yield |
---|---|
With iodobenzene complex with boron trifluoride etherate In dichloromethane at -10℃; | 80% |
With hypoiodous acid; acetone at -40 - 20℃; | |
Multi-step reaction with 2 steps 1: 92 percent / m-chloroperbenzoic acid / diethyl ether / Ambient temperature 2: 28 percent / PdCl2(MeCN)2, CuCl2, air / CH2Cl2 / 15 h / Ambient temperature; Irradiation View Scheme |
cis-stilben
A
Diphenylacetaldehyde
B
(E)-1,2-diphenyl-ethene
C
benzaldehyde
Conditions | Yield |
---|---|
2,4,6-triphenylpyrylium tetrafluoroborate for 4h; Product distribution; Irradiation; | A 7% B 80% C 12% |
Conditions | Yield |
---|---|
With hydrogenchloride; tin(ll) chloride In acetic acid for 0.05h; Heating; | 80% |
Multi-step reaction with 2 steps 1: amalgamated aluminium; diethyl ether 2: concentrated hydrochloric acid; glacial acetic acid View Scheme |
Diphenylacetaldehyde
((S)-2-Hydroxy-1-phenyl-ethylamino)-acetic acid methyl ester
((2S,4S)-2-Benzhydryl-4-phenyl-oxazolidin-3-yl)-acetic acid methyl ester
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane for 12h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene Heating; | 100% |
Conditions | Yield |
---|---|
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78 - 20℃; for 2h; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 0.5h; | 100% |
Diphenylacetaldehyde
2-cyclopentyl-2-phenylethen-1-one
(S)-Cyclopentyl-phenyl-acetic acid 2,2-diphenyl-vinyl ester
Conditions | Yield |
---|---|
With chiral (-)-ferrocene catalyst In chloroform at 0℃; for 22h; | 99% |
Diphenylacetaldehyde
2-cyclopentyl-2-phenylethen-1-one
(R)-Cyclopentyl-phenyl-acetic acid 2,2-diphenyl-vinyl ester
Conditions | Yield |
---|---|
With chiral (+)-ferrocene catalyst In chloroform at 0℃; for 22h; | 99% |
Diphenylacetaldehyde
2-(o-tolyl)but-1-en-1-one
2-o-tolyl-butyric acid 2,2-diphenyl-vinyl ester
Conditions | Yield |
---|---|
With chiral (+)-ferrocene catalyst In chloroform at 0℃; for 22h; | 99% |
Diphenylacetaldehyde
2-(o-tolyl)but-1-en-1-one
2-o-tolyl-butyric acid 2,2-diphenyl-vinyl ester
Conditions | Yield |
---|---|
With chiral (-)-ferrocene catalyst In chloroform at 0℃; for 22h; | 99% |
3-furan-2-yl-3-oxo-propionic acid methyl ester
Diphenylacetaldehyde
C22H18O4
Conditions | Yield |
---|---|
With piperidine; acetic acid In benzene at 100℃; for 16h; Knoevenagel condensation; Inert atmosphere; optical yield given as %de; | 99% |
Conditions | Yield |
---|---|
Stage #1: Diphenylacetaldehyde With [(N,N'-bis(diisopropylphosphino)-2,6-diaminopyridine)Mn(CO)2H] In 1,2-dimethoxyethane at 110℃; for 18h; Inert atmosphere; Sealed tube; Stage #2: With sodium hydroxide at 25℃; for 18h; Inert atmosphere; chemoselective reaction; | 98% |
With iron(II) fluoro{tris[2-(diphenylphosphino)phenyl]phospino}tetrafluoroborate; hydrogen; trifluoroacetic acid In isopropyl alcohol at 120℃; under 15001.5 Torr; for 2h; Inert atmosphere; Autoclave; chemoselective reaction; | 95% |
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating; | 90% |
Diphenylacetaldehyde
indole-3-acetic acid
2-(1-(2,2-diphenylvinyl)-1H-indol-3-yl)acetic acid
Conditions | Yield |
---|---|
Stage #1: Diphenylacetaldehyde; indole-3-acetic acid With trifluoroacetic acid In acetonitrile at 140℃; for 1h; Inert atmosphere; Microwave irradiation; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate; acetonitrile | 98% |
Diphenylacetaldehyde
4-hydroxybenzoic acid hydrazide
diphenylacetaldehyde p-hydroxybenzoylhydrazone
Conditions | Yield |
---|---|
With acetic acid In ethanol for 4h; Reflux; | 98% |
N-(2-iodophenyl)-4-methyl-N-(propa-1,2-dien-1-yl)benzenesulfonamide
Diphenylacetaldehyde
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); Benzhydrylamine; sodium t-butanolate In tetrahydrofuran at 50℃; for 8h; Inert atmosphere; Sealed tube; | 98% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); benzoic acid In 1,4-dioxane at 100℃; for 15h; | 97% |
Diphenylacetaldehyde
tert-butylamine
1-tert.-Butylamino-2,2-diphenylethylen
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane for 1h; Heating; | 96% |
1.3-propanedithiol
Diphenylacetaldehyde
2-(diphenylmethyl)-1,3-dithiane
Conditions | Yield |
---|---|
With 4 A molecular sieve; boron trifluoride diethyl etherate In dichloromethane Condensation; | 96% |
Diphenylacetaldehyde
1,1-diphenyl-3-butene-1-carboxaldehyde
Conditions | Yield |
---|---|
With ionic liquid; phosphine ligand; triethylamine; palladium catalyst at 20℃; for 5h; | 96% |
Diphenylacetaldehyde
p-toluenesulfonylanhydride
2,2-diphenylvinyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
Stage #1: Diphenylacetaldehyde With sodium t-butanolate In tetrahydrofuran at -20 - 20℃; for 1.5h; Inert atmosphere; Stage #2: p-toluenesulfonylanhydride In tetrahydrofuran at -15 - -5℃; for 1.5h; Inert atmosphere; | 96% |
Stage #1: Diphenylacetaldehyde With sodium t-butanolate In tetrahydrofuran at -20 - 20℃; Inert atmosphere; Stage #2: p-toluenesulfonylanhydride In tetrahydrofuran at -15 - -5℃; for 1.5h; Inert atmosphere; | 96% |
Diphenylacetaldehyde
5-methoxy-1H-indole-3-acetic acid
2-(5-methoxy-1-(2,2-diphenylvinyl)-1H-indol-3-yl)acetic acid
Conditions | Yield |
---|---|
Stage #1: Diphenylacetaldehyde; 5-methoxy-1H-indole-3-acetic acid With trifluoroacetic acid In acetonitrile at 140℃; for 1h; Inert atmosphere; Microwave irradiation; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate; acetonitrile | 96% |
The IUPAC name of this chemical is 2,2-diphenylacetaldehyde. With the CAS registry number 947-91-1, it is also named as alpha-Phenylbenzeneacetaldehyde. The product's categories are Aldehydes; C10 to C21; Carbonyl Compounds. It is clear colorless to pale yellow liquid which is stable under normal temperature and pressure. When use it, people should not breathe vapour and avoid contact with skin and eyes. Additioanally, this chemical should be sealed in the container which is filled with inert gas and stored in the cool and dry place.
The other characteristics of Diphenylacetaldehyde can be summarized as: (1)ACD/LogP: 3.67; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.67; (4)ACD/LogD (pH 7.4): 3.67; (5)ACD/BCF (pH 5.5): 360.96; (6)ACD/BCF (pH 7.4): 360.96; (7)ACD/KOC (pH 5.5): 2356.31; (8)ACD/KOC (pH 7.4): 2356.31; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.572; (13)Molar Refractivity: 60.38 cm3; (14)Molar Volume: 183.4 cm3; (15)Polarizability: 23.94×10-24 cm3; (16)Surface Tension: 41.5 dyne/cm; (17)Enthalpy of Vaporization: 55.36 kJ/mol; (18)Vapour Pressure: 0.000523 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Tautomer Count: 2; (21)Exact Mass: 196.088815; (22)MonoIsotopic Mass: 196.088815; (23)Topological Polar Surface Area: 17.1; (24)Heavy Atom Count: 15; (25)Complexity: 170.
Preparation of Diphenylacetaldehyde: It can be obtained by 2,2-diphenyl-oxirane. This reaction needs reagents ether BF3 and diethyl ether.
Uses of Diphenylacetaldehyde: It can react with acetic acid anhydride to get acetic acid-(2,2-diphenyl-vinyl ester). This reaction needs reagent sodium acetate.
People can use the following data to convert to the molecule structure.
1. SMILES:O=CC(c1ccccc1)c2ccccc2
2. InChI:InChI=1/C14H12O/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-11,14H
3. InChIKey:HLLGFGBLKOIZOM-UHFFFAOYAO
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 56mg/kg (56mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02088, |
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