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[ CAS No. 2142-66-7 ]

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2D
Chemical Structure| 2142-66-7
Chemical Structure| 2142-66-7
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Quality Control of [ 2142-66-7 ]

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Product Details of [ 2142-66-7 ]

CAS No. :2142-66-7MDL No. :MFCD00053707
Formula :C14H12OBoiling Point :337.4°C at 760 mmHg
Linear Structure Formula :C6H5C6H4COCH3InChI Key :XZWYAMYRMMMHKM-UHFFFAOYSA-N
M.W :196.24Pubchem ID :11159903
Synonyms :

Computed Properties of [ 2142-66-7 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 2142-66-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2142-66-7 ]

  • Downstream synthetic route of [ 2142-66-7 ]

[ 2142-66-7 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 2142-69-0 ]
  • [ 934-56-5 ]
  • [ 2142-66-7 ]
  • [ 1066-44-0 ]
  • 2
  • [ 591-50-4 ]
  • [ 308103-40-4 ]
  • [ 2142-66-7 ]
  • 3
  • [ 108-22-5 ]
  • [ 2142-66-7 ]
  • (R)-1-(biphenyl-2-yl)ethyl acetate [ No CAS ]
  • [ 16927-84-7 ]
  • 5
  • triethylammonium bis(1,2-benzenediolato)phenylsilicate [ No CAS ]
  • [ 129849-05-4 ]
  • [ 2142-66-7 ]
  • 6
  • [ 2142-66-7 ]
  • [ 79-19-6 ]
  • 1-(biphenyl-2-yl)ethanone (E)-thiosemicarbazone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In methanol;Heating / reflux; Biphenyl thiosemicarbazones la-lc were prepared in high yield (80-90%) from the biphenylacetophenones, which were in turn prepared in good yield (60-70%) (Scheme I) via a Suzuki cross coupling procedure from the corresponding bromoacetophenones and phenylboronic acid. Scheme I MyllH, sur er x I (i) Pd (Ph3P) 4K2C03 (aq), PhMe, reflux, phenylboronicacid. (ii) la=2'-phenyl thiosemicarbazide, MeoH, Ac OH, Reflux lb=3'-phenyl lc=4'-phenyl;1-Biphenyl-2-yl-ethanone thiosemicarbazone (la) : 1H NMR aH (400 MHz ; DMSO- d6) 1.77 (s, 3H), 7.25 (s, 1H), 7.31 (d, 2H, J =7. 6, ), 7.36 (d, 1H, J=2.0), 7.39 (d, 2H, J=9.2), 7.43 (s, 1H), 7.45 (s, 1H), 7.55 (d, 1H, J=8. 4), 8. 12 (s, 1H), 10.13 (s, 1H) and 11.95 (s, lH) ; MS (El) m/z 270.3 (MH+). Anal. (CisHisN3S) C, H, N, S.
  • 7
  • [ 2142-69-0 ]
  • [ 98-80-6 ]
  • [ 92-52-4 ]
  • [ 2142-66-7 ]
  • 9
  • [ 2142-66-7 ]
  • [ 368-78-5 ]
  • N-(1-biphenyl-2-yl-ethylidene)-N'-(3-trifluoromethyl-phenyl)-hydrazine [ No CAS ]
  • 10
  • [ 2142-69-0 ]
  • [ 98-80-6 ]
  • [ 2142-66-7 ]
YieldReaction ConditionsOperation in experiment
87% With potassium carbonate; palladium dichloride; In ethanol; water; at 20℃; for 1h; General procedure: A mixture of aryl bromide (0.5 mmol), arylboronic acid (0.75 mmol), PdCl2 (0.0025 mmol, 0.44 mg), K2CO3 (1 mmol) was stirred in distilled water (2 mL) and ethonal (2 mL) at room temperature in air for the indicated time. After the completion of the reaction, the mixture was quenched by brine (15 mL), extracted with diethyl ether (4×10 mL), dried by anhydrous MgSO4, concentrated under vacuum and the product was afforded by column chromatography on silica gel (200-300 mesh) eluted with petroleum ether and ethyl acetate.
85% With trans-{(1-ethyl-7-methyl-2-(4-fluorophenyl)-imidazol-3-ylidene[1,2-a]pyridine)}PdI2(pyridine); sodium hydroxide; In acetonitrile; at 85℃; for 14h; General procedure: In a typical catalysis run, a mixture of an aryl bromide (1.00 mmol), boronic acid (1.2 mmol), NaOH (1.5 mmol) and catalyst (1-4) (0.005 mmol, 0.5 mol %) in CH3CN (ca. 20 mL) was heated with stirring for 14 h at 85 C. The reaction mixture was then cooled to room temperature and the volatiles were removed under vacuum. The crude product thus obtained was extracted with ethyl acetate and further purified by column chromatography using silica gel as a stationary phase and eluting with a mixed medium of petroleum ether and EtOAc(v/v, 9:1) to give the desired products (5-14).
58% With sodium hydrogencarbonate; In water; for 2.08333h;Reflux; Green chemistry;Catalytic behavior; General procedure: A mixture of the appropriate aryl halide (1 mmol), phenylboronic acid (1.2 mmol), SiO2-acac-PdNPs catalyst(10 mg, 0.0004 mmol, 0.04 mol%), NaHCO3(2 mmol) was added to water (3 mL) in a round-bottom flask equipped with condenser and refluxed under heating conditions in reflux temperature. Themixture was stirred continuously during the reaction.After the reaction was completed (monitored by TLC, 90/10 hexane/EtOAc), the mixture was cooled to room temperature and the catalyst was separated by filtration, washed thrice with water and acetone and allowed to dry at room temperature for 30 min under vacuum for the next run. The reaction mixture was poured into a separating funnel and water (20 mL) and n-hexane (10 mL) were added and extracted for thrice. The combined organic phases were dried over CaCl2, filtered, and the solvent was evaporated. The residue was the products which were various biaryls. In some cases, the residue was purified by column chromatography (silica gel 60, EtOAc: n-hexane 10:90). All the products were known and characterized by melting point, IR and 1H NMR spectroscopy and were compared with authentic samples. The data were found to be identical to those reported in the literature.
31% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; for 48h;Reflux; General procedure: 2'- or 3'-Bromoacetophenone (10.05 mmol, 1 equiv) and phenylboronic acid (12.04 mmol, 1.2 equiv) were dissolved in a mixture of DME (30 mL) and H2O (30 mL). Then, K2CO3 (15.08 mmol, 1.5 equiv) and tetrakistriphenylphosphinepalladium (0.05 mol, 0.005 equiv) were added and the mixture was refluxed for 48 h. After cooling to room temperature, the suspension was filtered off and the filtrate was extracted with CH2Cl2. The resulting organic layer was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (cyclohexane/AcOEt, 6:4) to afford the corresponding derivatives 1 and 2.
12% With dichloro{1-(2-(bis(3,5-dimethylphenyl)phosphinyl)phenyl)-N-(tert-butyl)methanamine}-palladium(II); potassium carbonate; In water; N,N-dimethyl-formamide; at 80℃; for 12h;Schlenk technique; Inert atmosphere; General procedure: In a typical experiment, a sealed tube was charged with aryl bromide (0.10 mmol), phenylboronic acid (0.12 mmol), base (0.12 mmol), organic solvent-H2O (3:3 mL) and palladium catalyst (0.2 mol%), and the mixture was stirred at appropriate temperature. After the required reaction time, the mixture was cooled and poured out in CHCl3 (20 mL) and washed with saturated ammonium chloride and brine solution. Then, the organic phase was dried over anhydrous sodium sulfate, and the solvent was evaporated. The crude product was chromatographed on silica gel and the isolated biphenyl product was characterized by 1H,13C NMR, and GC.
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene;Heating / reflux; Biphenyl thiosemicarbazones la-lc were prepared in high yield (80-90%) from the biphenylacetophenones, which were in turn prepared in good yield (60-70%) (Scheme I) via a Suzuki cross coupling procedure from the corresponding bromoacetophenones and phenylboronic acid. Scheme I MyllH, sur er x I (i) Pd (Ph3P) 4K2C03 (aq), PhMe, reflux, phenylboronicacid. (ii) la=2'-phenyl thiosemicarbazide, MeoH, Ac OH, Reflux lb=3'-phenyl lc=4'-phenyl.
89%Chromat. With bis-[1-(2,4,6-diisopropylpheny)-3,4,5,6-tetrahydropyrimidine]dibromopalladium; potassium tert-butylate; In water; N,N-dimethyl-formamide; at 100℃; for 3h;Inert atmosphere; General procedure: A Schlenk tube was charged with the appropriate aryl halide, arylboronic acid and base under nitrogen. The required amount of the catalyst stock solution and additional solvent were added to obtain a total volume of 3 mL. The reaction mixture was heated at 100 C for specified time, and then allowed to cool. The reactionmixture was extracted three times with diethyl ether, and the combined organic extracts werewashed withwater, dried (MgSO4), and evaporated to dryness. Internal standard was added to the residue and the yield was then measured by GC. The products were isolated by flash chromatography on silica gel, and characterized by m.p. and 1H NMR.
With potassium phosphate; In N,N-dimethyl-formamide; at 100℃; General procedure: Unless otherwise stated, a mixture of 4'-bromoacetophenone(0.2149 g, 1.08 mmol), phenylboronic acid (0.1975 g, 1.62mmol), K3PO4 (0.8628 g, 3.24 mmol), and n-hexadecane (0.12ml) as the internal standard in dimethylformamide (5 ml) wereadded to a round-bottom flask containing the required amountof the immobilized palladium catalyst. The flask was heated atthe required temperature with magnetic stirring. Reaction conversions were monitored by withdrawing aliquots (0.1 ml)from the reaction mixture at different time intervals andquenching with water (1 ml). The organic components wereextracted into diethylether (2 ml 2), dried over Na2SO4, andanalyzed by GC with n-hexadecane as the reference. Theproduct identity was also further confirmed by GC-MS.
With C28H44Cl2N4O2Pd; potassium hydroxide; In water; isopropyl alcohol; at 60℃; for 3h;Schlenk technique; Sealed tube; General procedure: The Suzuki-Miyaura reactions were carried out in a Schlenk tube. Weighed amounts of the solid reactants: phenylboronic acid (135 mg; 1.1 mmol), KOH (112.0 mg; 2.0 mmol), catalyst (20.0 mg), 2-Br-toluene (0.118 mL; 1 mmol) and 5 mL of solvent (2-propanol/water mixture) were introduced to the Schlenk tube. Next, the Schlenk tube was sealed with a rubber septum and introduced into an oil bath preheated to 80 C. The reaction mixture was magnetically stirred at the given temperature for 6 h and after this time left for several minutes to cool down. Next, the organic products were separated by extraction with 10 mL of DEE. The extracts (10 mL) were GC-FID analyzed with dodecane (0.050 mL) as an internal standard to determine the conversion of aryl bromide.The products of the reaction were determined by GC-MS.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 110℃; for 11h;Inert atmosphere; adding tetrakis(triphenylphosphine)palladium (0.3 mmol, 346.7 mg) to anhydrous three-necked flask(9 mmol, 1.24 g), after sealing, the air in the bottle was exhausted and filled with nitrogen, and repeated once. Add to the three-necked flask in turn2'-Bromoacetophenone (3 mmol, 405 muL), a mixture of phenylboric acid (3.6 mmol, 435 mg) dissolved in 3 mL of ethanol, saturated with nitrogenAnd 12 mL of toluene. The reaction mixture is refluxed at 110 C for 11 hours to obtain an intermediate product of biphenyl B.ketone. Almost completely converted. Purification by silica gel column (petroleum ether: ethyl acetate = 100:1).

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