para-bromoacetophenone
4-acetylphenylboronic acid
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With potassium carbonate; N,N-diethylaminopropyl-Al2O3-Pd(OAc)2 In ethanol; water for 0.0833333h; Suzuki-Miyaura reaction; | 100% |
With potassium carbonate; Pd(NH3)2Cl2 In water at 100℃; for 3h; Suzuki cross-coupling reaction; | 99% |
With iron(III) chloride; potassium fluoride In ethanol at 90℃; for 16h; Suzuki-Miyaura type coupling; sealed tube; air; | 99% |
4-Iodoacetophenone
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; [2-(Pd-Cl)-4,4'-dichlorobenzophenone oxime]2 In decane; N,N-dimethyl-formamide at 110℃; for 5h; Ullmann homocoupling; | 99% |
With potassium iodide; nickel dibromide; zinc In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide at 50℃; for 3h; | 98% |
With potassium phosphate In water at 110℃; for 48h; Ullmann Condensation; | 98% |
Conditions | Yield |
---|---|
With sodium hydroxide; ascorbic acid In water at 80℃; for 3h; Catalytic behavior; Ullmann Condensation; | 99% |
With samarium; triphenylphosphine; nickel dichloride In N,N-dimethyl-formamide at 70℃; for 6h; | 98% |
With carbon dioxide; aluminium; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide at 65℃; under 116262 Torr; for 16h; Ullmann reaction; | 97% |
para-chloroacetophenone
4-acetylphenylboronic acid
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; potassium carbonate; Pd(NH3)2Cl2 In water at 140℃; for 5h; Suzuki cross-coupling reaction; | 99% |
With (η3-2-methylallyl)Pd(N3)(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); caesium carbonate In methanol at 80℃; for 1h; Suzuki-Miyaura Coupling; Schlenk technique; | 99% |
With potassium phosphate; tetrabutylammomium bromide In water at 95℃; for 40h; Suzuki-Miyaura Coupling; | 90% |
4-acetylphenylboronic acid
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With sodium hydroxide In water at 120 - 130℃; Microwave irradiation; | 99% |
With sodium carbonate; p-toluenesulfonyl chloride; palladium dichloride In ethanol; water at 20℃; for 12h; | 96% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium diacetate; tetraethylammonium perchlorate; potassium carbonate In water; acetonitrile at 20℃; Electrochemical reaction; Divided cell; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
Stage #1: acetyl chloride With aluminium trichloride In dichloromethane at 0℃; for 0.333333h; Stage #2: biphenyl In dichloromethane at 0 - 40℃; Friedel-Crafts acetylation; Further stages.; | 97.5% |
With carbon disulfide; aluminum (III) chloride for 4.83333h; Reflux; | 90% |
With aluminium trichloride In 1,2-dichloro-ethane for 12h; | 68% |
Conditions | Yield |
---|---|
With potassium phosphate; [NBu4][Pd(DMSO)Cl3]; hydroquinone In N,N-dimethyl-formamide at 140℃; for 3h; Temperature; Reagent/catalyst; Inert atmosphere; | 95% |
With bis(1,5-cyclooctadiene)nickel (0) In N,N-dimethyl-formamide at 45℃; for 36h; | 93% |
With potassium carbonate In ethanol; water at 20℃; for 12h; Ullmann Condensation; | 92% |
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With copper diacetate In ethanol; water dowex resin; Ullmann Condensation; Sonication; | 94% |
4-Iodoacetophenone
(Z)-2-(2,2-diisopropyl-1-oxa-2-silacyclopent-3-ylidene)acetaldehyde
A
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With copper(l) iodide; bis(η3-allyl-μ-chloropalladium(II)); [-MeSi(H)O-]3-5; potassium fluoride In N,N-dimethyl-formamide at 20℃; for 2h; | A 7% B 91% |
Conditions | Yield |
---|---|
With D-glucose; tetrabutylammonium acetate; palladium diacetate In water at 90℃; for 6h; Ullmann-type homocoupling reaction; | A 88% B 13% |
With potassium hydroxide In water; N,N-dimethyl-formamide at 35℃; for 24h; Ullmann Condensation; Inert atmosphere; | A 86% B 5% |
Conditions | Yield |
---|---|
bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 95℃; for 5h; Product distribution; catalysis with Pd*dba)2; other solvents; cross-coupling reactions of arenes with a hypervalent silicon reagent tetrabutylammonium triphenyldichlorosilicate; hetero- and homocoupled products; | A 86% B 14% |
para-bromoacetophenone
bis(pinacol)diborane
A
4,4'-diacetylbiphenyl
B
1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone
Conditions | Yield |
---|---|
With potassium acetate; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 3h; | A n/a B 86% |
With potassium acetate; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 18h; | |
With bis(tri-t-butylphosphine)palladium(0); potassium acetate In water at 20℃; for 6h; Miyaura Borylation Reaction; Inert atmosphere; Overall yield = 71 %; |
Conditions | Yield |
---|---|
With Pd(L-proline)2; potassium carbonate In water for 20h; Suzuki-Miyaura Coupling; Sealed tube; Reflux; | 84% |
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: 4-acetylphenylboronic acid With triethylamine In 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide; water at 20 - 110℃; Suzuki coupling; Ionic liquid; Inert atmosphere; |
para-bromoacetophenone
phenylboronic acid
A
biphenyl-4-acetaldehyde
B
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With potassium carbonate for 1.5h; Suzuki Coupling; Milling; | A 84% B 15% |
With potassium phosphate; C33H43N3Ni*F6P(1-) In toluene at 90℃; for 0.25h; Suzuki coupling; Inert atmosphere; | |
With potassium phosphate; C15H24ClN2Ni In toluene at 110℃; for 1h; Suzuki-Miyaura Cross-Coupling; Inert atmosphere; |
4-bromoethylbutanoate
para-bromoacetophenone
A
diethyl suberate
B
4,4'-diacetylbiphenyl
C
4-(4-acetylphenyl)butyric acid ethyl ester
D
butanoic acid ethyl ester
E
acetophenone
Conditions | Yield |
---|---|
With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 1,10-Phenanthroline; NiI2*3.5H2O; sodium iodide; zinc at 20 - 60℃; for 25h; chemoselective reaction; | A n/a B n/a C 84% D n/a E n/a |
4-Iodoacetophenone
(Z)-2-(2,2-diisopropyl-1-oxa-2-silacyclopent-3-ylidene)propanal
A
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With copper(l) iodide; bis(η3-allyl-μ-chloropalladium(II)); [-MeSi(H)O-]3-5; potassium fluoride In N,N-dimethyl-formamide at 20℃; for 7h; | A 14 % Spectr. B 83% |
4-Iodoacetophenone
phenylboronic acid
A
biphenyl-4-acetaldehyde
B
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With Br(1-)*C27H29BrN5Pd(1+); potassium carbonate In 1-methylpiperidin-2-one at 140℃; for 24h; Suzuki coupling; | A 83% B 12% |
With potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 12h; Suzuki-Miyaura reaction; Inert atmosphere; | A 70% B 15% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium carbonate In water; N,N-dimethyl-formamide at 20℃; for 2h; Catalytic behavior; Suzuki Coupling; Inert atmosphere; Irradiation; | A 68% B 14% |
With tributyl-amine; tetrabutylammomium bromide; oxime carbapalladacycle complex on Al In toluene at 110℃; for 72h; Suzuki-Miyaura cross-coupling; Title compound not separated from byproducts; |
1-(4-(tributylstannyl)phenyl)ethan-1-one
para-bromoacetophenone
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 0.116667h; Stille coupling; Microwave irradiation; | 83% |
4-vinylbenzyl chloride
4-Iodoacetophenone
A
4,4'-diacetylbiphenyl
B
C16H13ClO
Conditions | Yield |
---|---|
With C32H25ClNO2PPd; triethylamine at 130℃; for 1.5h; Catalytic behavior; Sealed tube; Green chemistry; | A 7% B 83% C 10% |
4-acetophenyl triflate
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; bis(pinacol)diborane; (diphenylphosphin)ferrocene In 1,4-dioxane at 80℃; for 14h; | 82% |
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With Pd(np)/Te-Dps; water at 100℃; for 10h; pH=8.9; Aerobic conditions; aq. Tris-HCl buffer; Combinatorial reaction / High throughput screening (HTS); | 82% |
1-(4-acetylphenyl)diazonium tetrafluoroborate
A
4,4'-diacetylbiphenyl
B
2-(p-acetylphenyl)benzofuran
Conditions | Yield |
---|---|
With bis(dibenzylideneacetone)-palladium(0) In water at 0 - 25℃; for 3h; Reagent/catalyst; Temperature; Time; Concentration; Suzuki-Miyaura Coupling; | A 16% B 82% |
4-Iodoacetophenone
phenyl tris(2,2,2-trifluoroethyl)siloxane
A
biphenyl-4-acetaldehyde
B
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; N,N-dimethyl-formamide at 95℃; for 2h; | A 78% B 16% |
Conditions | Yield |
---|---|
With phenyl tris(2,2,2-trifluoroethyl)siloxane; tetrabutyl ammonium fluoride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; N,N-dimethyl-formamide at 95℃; for 2h; | A 78% B 16% |
4-acetophenyl triflate
A
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; caesium carbonate In tetrahydrofuran for 72h; Suzuki-Miyaura reaction; Heating; | A n/a B 75% |
4-bromoethylbutanoate
para-chloroacetophenone
A
diethyl suberate
B
4,4'-diacetylbiphenyl
C
4-(4-acetylphenyl)butyric acid ethyl ester
D
butanoic acid ethyl ester
E
acetophenone
Conditions | Yield |
---|---|
With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 4,4'-Dimethoxy-2,2'-bipyridin; NiI2*3.5H2O; sodium iodide; zinc at 20 - 60℃; for 18h; chemoselective reaction; | A n/a B n/a C 75% D n/a E n/a |
Conditions | Yield |
---|---|
With palladium diacetate at 50℃; for 0.166667h; Microwave irradiation; | A n/a B 75% |
para-bromoacetophenone
A
4,4'-diacetylbiphenyl
B
p-BrZnPhCOCH3
C
acetophenone
Conditions | Yield |
---|---|
Stage #1: With Ethyl 4-bromobenzoate; trifluoroacetic acid; cobalt(II) bromide; zinc In hexanedinitrile; acetonitrile for 0.166667 - 0.5h; Stage #2: para-bromoacetophenone With zinc dibromide In hexanedinitrile; acetonitrile at 20℃; Product distribution / selectivity; | A 12% B 74% C 14% |
With Ethyl 4-bromobenzoate; trifluoroacetic acid; cobalt(II) bromide; zinc dibromide; zinc In acetonitrile at 0℃; for 0.416667h; Product distribution / selectivity; | A 23% B 59% C 8% |
4-acetophenyl triflate
A
4,4'-diacetylbiphenyl
B
1-[4-(3-chloropropyl)phenyl]ethanone
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; caesium carbonate In tetrahydrofuran for 72h; Suzuki-Miyaura reaction; Heating; | A n/a B 72% |
triethoxyphenylsilane
para-bromoacetophenone
A
biphenyl-4-acetaldehyde
B
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; water; palladium dichloride; P(p-C6H4F)3 In toluene at 120℃; for 3.5h; Hiyama coupling; Inert atmosphere; | A 72% B 16% |
4,4'-diacetylbiphenyl
α,α'-dimethyl-4,4'-biphenylenedimethanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 21℃; for 96h; Inert atmosphere; | 98% |
With hydrogen; nickel In ethanol at 60 - 70℃; under 11400.8 - 53203.6 Torr; for 1h; | 87% |
With sodium tetrahydroborate In isopropyl alcohol |
Conditions | Yield |
---|---|
With bromine; acetic acid at 20 - 50℃; for 24h; | 96% |
With bromine In dichloromethane for 1.25h; Flow reactor; | 93% |
Stage #1: 4,4'-diacetylbiphenyl With trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.25h; Stage #2: With N-Bromosuccinimide In dichloromethane at 0℃; for 2h; Concentration; | 92% |
4,4'-diacetylbiphenyl
1,1'−([1,1'−biphenyl]−4,4'−diyl)diethanol
Conditions | Yield |
---|---|
With (+)-β-chlorodiisopinocampheylborane In diethyl ether at 25℃; for 3h; | 94% |
With formic acid; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; triethylamine; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine at 40℃; for 25h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 94% |
Multi-step reaction with 3 steps 1: sodium borohydride / propan-2-ol 2: 29.1 percent / benzene / 10 h / Amano P lipoprotein lipase 3: 88 percent / NaOH / methanol View Scheme | |
Multi-step reaction with 2 steps 1: 1) sodium borohydride, 2) acetic anhydride / 1) isopropanol, 2) benzene, Amano P lipoprotein lipase, 10 h 2: 88 percent / NaOH / methanol View Scheme |
4,4'-diacetylbiphenyl
4,4'-diacetyldiphenyl dioxime
Conditions | Yield |
---|---|
With pyridine; hydroxylamine hydrochloride at 60℃; for 3.5h; | 93% |
Conditions | Yield |
---|---|
With hydrogen bromide In dimethyl sulfoxide at 60℃; for 18h; | 91% |
With selenium(IV) oxide | |
With selenium(IV) oxide In 1,4-dioxane Heating; | |
With iodine; dimethyl sulfoxide at 20 - 130℃; Kornblum Aldehyd Synthesis; Sealed tube; |
4,4'-diacetylbiphenyl
(S,S)−1,1'−([1,1'−biphenyl]−4,4'−diyl)diethanol
Conditions | Yield |
---|---|
With (-)-diisopinocamphenylborane chloride In dichloromethane at -25℃; for 3h; | 90% |
With E.coli alcohol dehydrogenase In 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide; isopropyl alcohol at 30℃; for 18h; pH=8.3; aq. buffer; Ionic liquid; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
4,4'-diacetylbiphenyl
borontrifluoride acetic acid
Conditions | Yield |
---|---|
With acetic anhydride at 45℃; for 4h; Inert atmosphere; | 90% |
3,3'-dinonanoylbenzidine
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With diphenyl hydrogen phosphate In various solvent(s) at 140℃; for 72h; | 85% |
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water at 80℃; for 0.5h; Inert atmosphere; | 85% |
4,4'-diacetylbiphenyl
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 80℃; for 0.5h; Inert atmosphere; | 85% |
IUPAC Name: 1-[4-(4-Acetylphenyl)phenyl]ethanone
Empirical Formula: C16H14O2
Molecular Weight: 238.2812
Canonical SMILES: CC(=O)C1=CC=C(C=C1)C2=CC=C(C=C2)C(=O)C
InChI: InChI=1S/C16H14O2/c1-11(17)13-3-7-15(8-4-13)16-9-5-14(6-10-16)12(2)18/h3-10H,1-2H3
InChIKey: YSTSBXDVNKYPTR-UHFFFAOYSA-N
XLogP3: 3.7
H-Bond Donor: 0
H-Bond Acceptor: 2
Index of Refraction: 1.564
Molar Refractivity: 70.9 cm3
Molar Volume: 217.7 cm3
Surface Tension: 40.9 dyne/cm
Density: 1.094 g/cm3
Flash Point: 144.9 °C
Enthalpy of Vaporization: 63.54 kJ/mol
Boiling Point: 386.5 °C at 760 mmHg
Vapour Pressure: 3.54E-06 mmHg at 25 °C
Melting Point: 193-195 °C(lit.)
Product Categories of 4,4'-Diacetylbiphenyl (CAS NO.787-69-9): Aromatic Acetophenones & Derivatives (substituted); Biphenyl & Diphenyl ether; Biphenyls (for High-Performance Polymer Research); Functional Materials; Reagent for High-Performance Polymer Research; C15 to C38; Carbonyl Compounds; Ketones
4,4'-Diacetylbiphenyl (CAS NO.787-69-9) is used as intermediates of liquid crystals.
Hazard Codes: N,Xi,Xn
Risk Statements: 50/53-36/37/38-20/21/22
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 60-61-36/37/39-26-37/39-36
S60:This material and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
S36:Wear suitable protective clothing.
RIDADR: UN 3077 9/PG 3
WGK Germany: 3
Hazard Note of 4,4'-Diacetylbiphenyl (CAS NO.787-69-9): Irritant
4,4'-Diacetylbiphenyl (CAS NO.787-69-9), its Synonyms are 1-(4'-Acetyl[1,1'-biphenyl]-4-yl)ethan-1-one ; Bis-acetophenone ; 1-(4'-Acetyl-biphenyl-4-yl)-ethaone ; 4',4''-Biacetophenone ; 1-(4'-Acetyl[1,1'-biphenyl]-4-yl)ethanone ; 4,4'-Diacetylbiphenyl,98% . It is white solid.
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