Conditions | Yield |
---|---|
With magnesium(II) perchlorate; oxygen; 9,10-Dicyanoanthracene In acetonitrile for 3h; Thermodynamic data; Mechanism; Rate constant; Irradiation; with and without singlet oxygen senzitizers, in less polar solvents; addition of 1,4-diazabicyclo<2.2.2>octane; ΔG; fluorescence quenching rate const.; var. biphenyls and terphenyls; | 100% |
With hydrogen bromide; dihydrogen peroxide In dichloromethane; water at 20℃; for 12h; | 85% |
With air; Ag/AgBr/TiO2 nanotubes In neat (no solvent) at 20℃; for 12h; Irradiation; Green chemistry; | 84% |
Conditions | Yield |
---|---|
With potassium phosphate; catacxium A; palladium diacetate In toluene at 100℃; for 20h; Suzuki cross-coupling reaction; | 100% |
With potassium phosphate; N,N-diisopropyl 2-dicyclohexylphosphino-4-phenylbenzamide; tris(dibenzylideneacetone)dipalladium (0) In tetrahydrofuran at 65℃; for 4h; Suzuki cross-coupling reaction; | 100% |
With 1,4-diaza-bicyclo[2.2.2]octane; caesium carbonate; palladium diacetate In N,N-dimethyl-formamide at 110℃; for 17h; Suzuki-Miyaura cross-coupling; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate; {1,3-di[(R)-1-PhEt]imidazolin-2-ylidene}(PPh3)PdI2 In xylene at 130℃; for 13h; Suzuki-Miyaura cross-coupling reaction; | 100% |
With tetrabutylammomium bromide; potassium carbonate; quasi polymeric 4-pyridine-aldoxime Pd(II)-catalyst at 120℃; for 0.333333h; Suzuki-Miyaura reaction; microwave irradiation; | 100% |
With 3-tert-butyl-5-methyl-1-(2-(diphenylphosphino)phenyl)-1H-pyrazole; tris(dibenzylideneacetone)dipalladium (0) In toluene at 65℃; for 2h; Suzuki coupling; | 100% |
Conditions | Yield |
---|---|
With aluminium trichloride; acetophenone oxime; 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate at 20℃; | 100% |
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In 1,2-dichloro-ethane at 120℃; under 7600 Torr; for 7.5h; | 100% |
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In 1,2-dichloro-ethane at 120℃; under 7500.6 Torr; for 7.5h; | 100% |
Conditions | Yield |
---|---|
{1,3-di[(R)-1-PhEt]imidazolin-2-ylidene}(PCPh)PdI2 In toluene at 110℃; for 17h; Stille reaction; | 100% |
With 1,4-diaza-bicyclo[2.2.2]octane; potassium hydroxide; poly(ethylene glycol)-400; palladium diacetate In water at 80℃; for 10h; Stille coupling; | 100% |
With potassium carbonate; trans-(1,3-di(1'-(R)-phenylethyl)imidazolin-2-ylidene)(tricyclohexylphosphine)palladium(II) diiodide In toluene at 110℃; for 17h; Stille cross coupling; | 99% |
Conditions | Yield |
---|---|
With aluminium trichloride; 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate; (3,4-dimethoxyphenyl)methanol for 0.0333333h; | 100% |
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 2.5h; Heating; | 99% |
With K5 In acetone for 0.166667h; Heating; | 97% |
4-Iodoacetophenone
biphenyl-4-acetaldehyde
Conditions | Yield |
---|---|
bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 95℃; for 21h; | 100% |
Conditions | Yield |
---|---|
With trihexyl(tetradecyl)phosphonium chloride; potassium phosphate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In toluene at 50℃; for 1h; Suzuki cross-coupling; | 100% |
Stage #1: 4-Iodoacetophenone With tetrakis(triphenylphosphine) palladium(0) In 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide at 20 - 110℃; Suzuki coupling; Inert atmosphere; Ionic liquid; Stage #2: phenylboronic acid With triethylamine In 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide; water at 20 - 110℃; Suzuki coupling; Ionic liquid; Inert atmosphere; | 100% |
With potassium carbonate In ethanol; water at 20℃; for 0.5h; Suzuki-Miyaura reaction; in air; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol at 100℃; for 4h; Suzuki Coupling; High pressure; Green chemistry; | 100% |
With potassium carbonate In ethanol at 80℃; for 12h; Suzuki-Miyaura coupling; Inert atmosphere; | 99% |
With potassium carbonate In ethanol at 80℃; for 12h; Suzuki coupling; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; palladium diacetate; potassium hydroxide In tetrahydrofuran; water at 24℃; for 0.0833333h; Suzuki-Miyaura Coupling; Flow reactor; | 100% |
With C24H30N4O7; potassium carbonate; palladium dichloride In water at 20℃; for 1.5h; Suzuki coupling; | 99% |
With potassium carbonate In water at 25℃; for 18h; Suzuki-Miyaura Coupling; | 99% |
para-bromoacetophenone
phenylboronic acid
A
biphenyl-4-acetaldehyde
B
bromoboronate
Conditions | Yield |
---|---|
With K2CO3; diiodo(1,3-di[(R)-1-phenylethyl]imidazolin-2-ylidene)(triphenylphosphino)palladium(II) In xylene the mixt. in xylene was heated at 130°C for 13 h (N2); H2O was added, the aq. phase was extd. with diethyl ether, the organic phase was dried over MgSO4; | A 100% B n/a |
With K2CO3; di-μ-iodobis(1,3-di[(R)-1-phenylethyl]imidazolin-2-ylidene)diiododipalladium(II) In xylene the mixt. in xylene was heated at 130°C for 14 h (N2); H2O was added, the aq. phase was extd. with diethyl ether, the organic phase was dried over MgSO4; | A 99% B n/a |
tributylphenylstannane
para-bromoacetophenone
A
biphenyl-4-acetaldehyde
B
tributyltin bromide
Conditions | Yield |
---|---|
diiodo(1,3-di[(R)-1-phenylethyl]imidazolin-2-ylidene)(triphenylphosphino)palladium(II) In toluene toluene, 110°C, 17 h (N2); H2O was added, the aq. phase was extd. with diethyl ether, the organic phase was dried over MgSO4; | A 100% B n/a |
diiodo(1,3-di-tert-butylimidazolin-2-ylidene)(triphenylphosphino)palladium(II) In toluene toluene, 110°C, 17 h (N2); H2O was added, the aq. phase was extd. with diethyl ether, the organic phase was dried over MgSO4; | A 72% B n/a |
diiodo(1,3-di[(R)-1-phenylethyl]imidazolin-2-ylidene)(tri-o-tolylphosphino)palladium(II) In toluene toluene, 110°C, 17 h (N2); H2O was added, the aq. phase was extd. with diethyl ether, the organic phase was dried over MgSO4; | A 65% B n/a |
para-bromoacetophenone
phenylboronic acid
A
biphenyl-4-acetaldehyde
B
4-Bromobenzoic acid
C
biphenyl-4-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: para-bromoacetophenone; phenylboronic acid; immobilized 4-bromobenzoic acid With potassium carbonate In water; N,N-dimethyl-formamide Stage #2: With potassium hydroxide In ethanol; water | A 100% B 19% C 81% |
Conditions | Yield |
---|---|
With Br(1-)*C24H31BrN5O6Pd(1+); sodium hydroxide In water at 160℃; for 2h; Hiyama coupling; Sealed tube; | 99% |
With potassium fluoride; propylene glycol; chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium In dichloromethane at 100℃; for 12h; Hiyama Coupling; Inert atmosphere; | 99% |
With sodium hydroxide; 4,4'-dichlorobenzophenone oxime-derived palladacycle at 120℃; under 7500.6 Torr; for 0.166667h; Hiyama coupling; microwave irradiation; | 98% |
Conditions | Yield |
---|---|
With 3-(dicyclohexylphosphino)-2-(2-methoxyphenyl)-1-methyl-1-H-indole; tetrabutyl ammonium fluoride; palladium diacetate In water at 110℃; for 3h; Hiyama Coupling; Schlenk technique; Inert atmosphere; Sealed tube; | 99% |
With tBu2P-N=P(iBuPCH2CH2)3N; tetrabutyl ammonium fluoride; palladium diacetate In 1,4-dioxane at 80℃; for 1.5h; Hiyama coupling; Inert atmosphere; | 95% |
With tetrabutyl ammonium fluoride; palladium(II) acetylacetonate; 3,9-bis(2,4-tBu-PhO)tetraoxa-3,9-diphosphaspiro[5.5]undecane In xylene at 80℃; Hiyama coupling; | 93% |
(1-biphenyl-4-yl-ethoxy)-trimethyl-silane
biphenyl-4-acetaldehyde
Conditions | Yield |
---|---|
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.25h; Heating; | 99% |
With aluminium trichloride; tetramethylammonium chlorochromate In acetonitrile for 0.916667h; Heating; | 96% |
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In dichloromethane for 0.0833333h; microwave irradiation; | 92% |
4-acetylphenyl p-toluenesulfonate
phenylboronic acid
biphenyl-4-acetaldehyde
Conditions | Yield |
---|---|
With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); tricyclohexylphosphine tetrafluoroborate; potassium carbonate In water; toluene at 20℃; for 24h; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere; | 99% |
With potassium phosphate; Ni(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)[P(OPh)3]2 In tetrahydrofuran at 70℃; for 18h; Suzuki-Miyaura Coupling; Sealed tube; | 96% |
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride; tricyclohexylphosphine In 1,4-dioxane at 130℃; Suzuki cross-coupling; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide; palladium diacetate In water at 110℃; for 2h; Suzuki-type reaction; | 99% |
With tetrabutylammomium bromide; potassium carbonate In water at 120℃; for 0.25h; Suzuki cross-coupling reaction; Microwave irradiation; solid phase reaction; | 95% |
With sodium carbonate; palladium dichloride In methanol at 20℃; for 0.5h; Suzuki-Miyaura cross-coupling reaction; | 93% |
Conditions | Yield |
---|---|
Stage #1: poly(phenylmethylsiloxane) With tetrabutyl ammonium fluoride In 1,4-dioxane at 20℃; for 1h; Stage #2: para-chloroacetophenone; (bis(tricyclohexyl)phosphine)palladium(II) dichloride In 1,4-dioxane at 100℃; | 99% |
2-phenyl[1,3,2]dioxaborolane
4-Iodoacetophenone
biphenyl-4-acetaldehyde
Conditions | Yield |
---|---|
With potassium phosphate; aluminum oxide; ruthenium In 1,2-dimethoxyethane; water at 60℃; for 12h; Suzuki-Miyaura-type cross coupling reaction; | 99% |
Conditions | Yield |
---|---|
With water; palladium diacetate; sodium carbonate at 80℃; for 2h; Time; Suzuki Coupling; Green chemistry; | 99% |
With palladium diacetate; sodium carbonate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In water at 80℃; for 2h; Suzuki-Miyaura Coupling; | 99% |
With C14H21B10ClN2O2Pd*H2O; potassium carbonate In water at 110℃; for 10h; Reagent/catalyst; Suzuki Coupling; | 99% |
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
para-bromoacetophenone
biphenyl-4-acetaldehyde
Conditions | Yield |
---|---|
With caesium carbonate In methanol at 60℃; for 24h; Suzuki-Miyaura reaction; Inert atmosphere; | 99% |
With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere; | 99% |
With potassium phosphate; (C5H5FeC5H3C(CH3)NC6H4CH3)PdCl(tricyclohexylphosphine); potassium acetate In 1,4-dioxane; water at 100℃; for 3h; Suzuki coupling; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With potassium phosphate; (NC5H3(N2C7H4(CH2)3CH3)2)NiBr(1+)*Br(1-)=Ni(NC5H3(N2C7H4(CH2)3CH3)2)Br2; triphenylphosphine In 1,4-dioxane at 100℃; for 24h; Suzuki-Miyaura coupling; | 99% |
1‐([1,1'‐biphenyl]‐4‐yl)‐2,2‐dibromoethan‐1‐one
biphenyl-4-acetaldehyde
Conditions | Yield |
---|---|
With sodium hydrogen telluride In ethyl acetate for 1h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; meso-5,10,15,20-tetraphenyl-21-monothiaporphyrin; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 22℃; for 18h; Irradiation; | 98% |
With trimethylsilyl iodide In chloroform Ambient temperature; or reflux; | 95% |
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 3h; Ambient temperature; | 93% |
Conditions | Yield |
---|---|
With quinolinium dichromate(VI) In acetonitrile for 2h; Heating; | 98% |
With benzyltriphenylphosphonium dichromate; silica gel for 0.25h; | 94% |
With 3-carboxypyridinium chlorochromate In acetonitrile for 2h; Heating; | 84% |
With Oxone; water; potassium hydrogencarbonate In acetone for 0.666667h; Heating; | 58% |
4-acetylbiphenyl oxime
biphenyl-4-acetaldehyde
Conditions | Yield |
---|---|
With aluminium trichloride; benzyltriphenylphosphonium chlorochromate In acetonitrile for 0.416667h; Heating; | 98% |
With 1,4-dibenzyl-1,4-diazoniabicyclo[2.2.2]octane chlorochromate In acetonitrile for 0.25h; Heating; | 97% |
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 1.25h; Heating; | 92% |
1-(1-biphenyl-4-yl-ethylidene)-2-phenylhydrazine
biphenyl-4-acetaldehyde
Conditions | Yield |
---|---|
With 1-benzyl-4-aza-1-azoniabiyclo<2.2.2>octane peroxodisulfate In acetonitrile for 0.833333h; Heating; | 98% |
With benzyltriphenylphosphonium dichromate In acetonitrile for 0.416667h; Oxidation; Heating; | 98% |
With quinolinium dichromate(VI) In acetonitrile for 0.75h; Heating; | 98% |
4-Iodoacetophenone
2-phenyl-1,3,2-benzodioxaborole
biphenyl-4-acetaldehyde
Conditions | Yield |
---|---|
With potassium carbonate; aluminum oxide; ruthenium In 1,2-dimethoxyethane; water at 80℃; for 12h; Suzuki-Miyaura-type cross coupling reaction; | 98% |
Conditions | Yield |
---|---|
With bromine In 1,4-dioxane; diethyl ether for 0.5h; Ambient temperature; | 100% |
With phenyltrimethylammonium bromide dibromide In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere; | 100% |
With pol(vinylphenyltrimethylammoniumtribromide) resin In methanol; water at 65℃; for 1h; | 97% |
biphenyl-4-acetaldehyde
oxalic acid diethyl ester
ethyl 3-(4-phenylbenzoyl)-2-ketopropionate
Conditions | Yield |
---|---|
Stage #1: biphenyl-4-acetaldehyde With lithium hexamethyldisilazane In tetrahydrofuran; dichloromethane at -78℃; for 0.75h; Stage #2: oxalic acid diethyl ester In tetrahydrofuran; dichloromethane at 0 - 20℃; for 16h; Stage #3: With water; ammonium chloride In tetrahydrofuran; dichloromethane | 100% |
With sodium ethanolate In benzene for 4.5h; Ambient temperature; | 70% |
With sodium | |
Stage #1: oxalic acid diethyl ester With sodium ethanolate In toluene for 0.166667h; Cooling with ice; Stage #2: biphenyl-4-acetaldehyde In toluene for 4h; Cooling with ice; | |
With sodium In diethyl ether at 20 - 40℃; |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 35 - 40℃; for 2.5h; | 100% |
With sodium hydroxide In ethanol | |
With sodium hydroxide In ethanol; water for 0.5h; Heating; |
biphenyl-4-acetaldehyde
4-acetylbiphenyl oxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux; | 100% |
With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 95℃; | 100% |
96% |
Conditions | Yield |
---|---|
With trichloro(trifluoromethanesulfonato)titanium(IV) at 90 - 100℃; for 10h; | 99% |
With phosphomolybdic acid In ethanol for 4h; Reflux; | 92% |
With para-dodecylbenzenesulfonic acid In neat (no solvent) at 130℃; for 3h; Green chemistry; | 92% |
Conditions | Yield |
---|---|
With hydrogenchloride; palladium 10% on activated carbon; zinc In water at 50℃; | 99% |
With chlorobenzene In methanol at 40℃; for 4h; Sealed tube; Green chemistry; chemoselective reaction; | 99% |
With palladium 10% on activated carbon; hydrogen In ethanol at 100℃; under 760.051 - 1520.1 Torr; for 24h; Reagent/catalyst; | 99% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; Dowex1-x8 In tetrahydrofuran for 2.8h; Heating; | 99% |
With sodium tetrahydroborate In tetrahydrofuran for 1.8h; Heating; ultrasound irradiation; | 99% |
With diethoxymethylane; iron(II) acetate In tetrahydrofuran at 65℃; for 24h; | 99% |
biphenyl-4-acetaldehyde
1,2-Di-biphenyl-1,2-dimethyl-1,2-ethandiol
Conditions | Yield |
---|---|
With 2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester; Cu(5-(4-fluorosulfonyl)amino-3-(2-pyridyl)-pyrazole)((rac)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene)BF4 In tetrahydrofuran for 18h; Pinacol Rearrangement; Irradiation; | 99% |
With lithium amalgam; (S,S)-(+)-N,N,N',N'-tetramethyl-1,4-diamino-2,3-dimethoxybutane for 20h; Ambient temperature; | 86% |
With samarium diiodide In tetrahydrofuran for 2h; Ambient temperature; | 48% |
With aluminium amalgam |
biphenyl-4-acetaldehyde
(S)-1-(p-biphenyl)ethanol
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C53H73FeN2O2PS; hydrogen; lithium tert-butoxide In isopropyl alcohol at 25 - 30℃; under 22801.5 Torr; for 12h; Autoclave; enantioselective reaction; | 99% |
With (mer-[(S,S)-1,5-dimethyl-2,4-bis(4-phenyl-1,3-oxazolin-2-yl)benzene(1-)]Ru(CO)Cl)2(ZnCl2); hydrogen; sodium methylate; (-)-(S)-1-Anthracen-9-ylethanol In isopropyl alcohol at 40℃; under 22801.5 Torr; for 24h; Inert atmosphere; Autoclave; optical yield given as %ee; enantioselective reaction; | 98% |
With Debaryomyces hansenii P1 at 30℃; for 48h; pH=5.5; Microbiological reaction; enantioselective reaction; | 92% |
The Ethanone, 1-(1,1'-biphenyl)-4-yl-, with the CAS registry number 92-91-1 and EINECS registry number 202-202-6, has the systematic name of 1-(biphenyl-4-yl)ethanone. And the molecular formula of this chemical is C14H12O. It is a kind of off-white to beige powder, and belongs to the following product categories: Fine chemical & intermediates; Biphenyl derivatives; API intermediates; Adehydes, Acetals & Ketones. What's more, it is an inhibitor of renieratene, and it is also used in the organic synthesis. In addition, it is used intermediates of liquid crystals.
The physical properties of Ethanone, 1-(1,1'-biphenyl)-4-yl- are as following: (1)ACD/LogP: 3.51; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.51; (4)ACD/LogD (pH 7.4): 3.51; (5)ACD/BCF (pH 5.5): 274.52; (6)ACD/BCF (pH 7.4): 274.52; (7)ACD/KOC (pH 5.5): 1937.02; (8)ACD/KOC (pH 7.4): 1937.02; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 17.07 Å2; (13)Index of Refraction: 1.567; (14)Molar Refractivity: 60.87 cm3; (15)Molar Volume: 186.2 cm3; (16)Polarizability: 24.13×10-24cm3; (17)Surface Tension: 39.1 dyne/cm; (18)Density: 1.053 g/cm3; (19)Flash Point: 139.9 °C; (20)Enthalpy of Vaporization: 56.82 kJ/mol; (21)Boiling Point: 326 °C at 760 mmHg; (22)Vapour Pressure: 0.000222 mmHg at 25°C.
Uses of Ethanone, 1-(1,1'-biphenyl)-4-yl-: It can react with morpholine to produce 4-(biphenyl-4-yl-thioacetyl)-morpholine. This reaction will need reagent sulfur. The reaction time is 4 minutes with microwave irradiation, and the yield is about 95%.
You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; Do not breathe dust; Avoid contact with skin and eyes.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(c2ccc(c1ccccc1)cc2)C
(2)InChI: InChI=1/C14H12O/c1-11(15)12-7-9-14(10-8-12)13-5-3-2-4-6-13/h2-10H,1H3
(3)InChIKey: QCZZSANNLWPGEA-UHFFFAOYAF
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | > 2gm/kg (2000mg/kg) | Medicina Experimentalis. Vol. 11, Pg. 137, 1964. |
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