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[ CAS No. 156642-03-4 ]

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Chemical Structure| 156642-03-4
Chemical Structure| 156642-03-4
Structure of 156642-03-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 156642-03-4 ]

CAS No. :156642-03-4 MDL No. :MFCD04039030
Formula : C13H13BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :VIHQQLWZRRVBNE-UHFFFAOYSA-N
M.W :228.05 g/mol Pubchem ID :4197354
Synonyms :

Safety of [ 156642-03-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 156642-03-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 156642-03-4 ]

[ 156642-03-4 ] Synthesis Path-Downstream   1~58

  • 1
  • [ 7342-82-7 ]
  • [ 156642-03-4 ]
  • [ 250279-13-1 ]
YieldReaction ConditionsOperation in experiment
85% With palladium diacetate; potassium carbonate In acetone at 65℃; for 2h;
  • 2
  • [ 43181-78-8 ]
  • [ 156642-03-4 ]
  • [ 250342-76-8 ]
  • 3
  • [ 250342-79-1 ]
  • [ 156642-03-4 ]
  • [ 263759-70-2 ]
YieldReaction ConditionsOperation in experiment
24% With palladium diacetate; potassium carbonate at 65℃; for 24h;
  • 4
  • [ 37055-19-9 ]
  • [ 156642-03-4 ]
  • 3,3',5,5'-tetrakis(4'-methoxybiphenyl-4-yl)bimesityl [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In toluene at 110℃; for 16h;
  • 5
  • [ 58743-83-2 ]
  • [ 156642-03-4 ]
YieldReaction ConditionsOperation in experiment
80% With n-butyllithium; Trimethyl borate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 20℃; for 1h;
Stage #1: 4-bromo-4'-methoxylbiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78 - -65℃; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -65 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; Further stages.;
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 1.2: 17 h / -78 - 66 °C / Inert atmosphere 2.1: hydrogenchloride / water; tetrahydrofuran / 2 h / 23 °C / Inert atmosphere
  • 6
  • [ 226072-71-5 ]
  • [ 156642-03-4 ]
  • [ 1011288-02-0 ]
YieldReaction ConditionsOperation in experiment
76% With sodium carbonate In ethanol; toluene for 2h; Heating / reflux; 3-Methoxy-l-(4'-methoxy-4-biphenyl)naphthalene; A mixture of 3-methoxynaphthalen-l-yl trifluoromethanesulfonate (0.5 g, 1.7 mmol), (4'-methoxy-4-biphenyl)boronic acid (0.58 g, 2.5 mmol), Na2CO3 (0.27 g, 2.5 mmol) and Pd(PPh3 )4 (40 mg, 2 mol %) in PhMe (20 ml) and EtOH (20 ml) under N2 was heated at reflux. After 2 h the mixture was cooled, poured into water (100 ml), extracted with dichloromethane (3 x 50 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane, filtered through a short plug of silica and the solvent removed under reduced pressure to give the title compound (0.44 g, 76 %) as a colourless powder.
76% With sodium carbonate In ethanol; toluene for 2h; Heating / reflux; 3-Methoxy-l-(4'-methoxy-4-biphenyl)naphthalene; A mixture of 3-methoxynaphthalen-l-yl trifluoromethanesulfonate (0.5 g, 1.7 mmol), (4'-methoxy-4-biphenyl)boronic acid (0.58 g, 2.5 mmol), Na2CO3 (0.27 g, 2.5 mmol) and Pd(PPh3)4 (40 mg, 2 mol %) in PhMe (20 ml) and EtOH (20 ml) under N2 was heated at reflux. After 2 h the mixture was cooled, poured into water (100 ml), extracted with dichloromethane (3 x 50 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane, filtered through a short plug of silica and the solvent removed under reduced pressure to give the title compound (0.44 g, 76 %) as a colourless powder.
76% With sodium carbonate In ethanol; toluene for 2h; Heating / reflux; 3-Methoxy-l-(4'-methoxy-4-biphenyl)naphthalene; A mixture of 3-methoxynaphthalen-l-yl trifluoromethanesulfonate (0.5 g, 1.7 mmol), (4'-methoxy-4-biphenyl)boronic acid (0.58 g, 2.5 mmol), Na2CO3 (0.27 g, 2.5 mmol) and Pd(PPh3)4 (40 mg, 2 mol %) in PhMe (20 ml) and EtOH (20 ml) under N2 was heated at reflux. After 2 h the mixture was cooled, poured into water (100 ml), extracted with dichloromethane (3 x 50 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane, filtered through a short plug of silica and the solvent removed under reduced pressure to give the title compound (0.44 g, 76 %) as a colourless powder.
76% With sodium carbonate In ethanol; dichloromethane; toluene 3-Methoxy-1-(4'-methoxy-4-biphenyl)naphthalene 3-Methoxy-1-(4'-methoxy-4-biphenyl)naphthalene A mixture of 3-methoxynaphthalen-1-yl trifluoromethanesulfonate (0.5 g, 1.7 mmol), (4'-methoxy-4-biphenyl)boronic acid (0.58 g, 2.5 mmol), Na2CO3 (0.27 g, 2.5 mmol) and Pd(PPh3)4 (40 mg, 2 mol %) in PhMe (20 ml) and EtOH (20 ml) under N2 was heated at reflux. After 2 h the mixture was cooled, poured into water (100 ml), extracted with dichloromethane (3*50 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane, filtered through a short plug of silica and the solvent removed under reduced pressure to give the title compound (0.44 g, 76%) as a colourless powder.
76% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene for 2h; Inert atmosphere; Reflux; 3-Methoxy-1-(4'-methoxy-4-biphenyl)naphthalene 3-Methoxy-1-(4'-methoxy-4-biphenyl)naphthalene A mixture of 3-methoxynaphthalen-1-yl trifluoromethanesulfonate (0.5 g, 1.7 mmol), (4'-methoxy-4-biphenyl)boronic acid (0.58 g, 2.5 mmol), Na2CO3 (0.27 g, 2.5 mmol) and Pd(PPh3)4 (40 mg, 2 mol %) in PhMe (20 ml) and EtOH (20 ml) under N2 was heated at reflux. After 2 h the mixture was cooled, poured into water (100 ml), extracted with dichloromethane (3*50 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane, filtered through a short plug of silica and the solvent removed under reduced pressure to give the title compound (0.44 g, 76%) as a colourless powder.

  • 7
  • [ 17878-23-8 ]
  • [ 156642-03-4 ]
  • [ 943024-31-5 ]
YieldReaction ConditionsOperation in experiment
51% With sodium carbonate In tetrahydrofuran; water for 48h; Heating;
  • 8
  • C12H12O2 [ No CAS ]
  • [ 156642-03-4 ]
  • C25H22O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With silver hexafluoroantimonate; tetrafluoroboric acid In water; isopropyl alcohol at 10℃; for 21h;
  • 9
  • [ 3141-27-3 ]
  • [ 156642-03-4 ]
  • 2,5-bis(4'-methoxybiphenyl-4-yl)thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In various solvent(s) at 85℃;
  • 10
  • [ 156642-03-4 ]
  • [ 943024-36-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 51 percent / Na2CO3 / tetrakis(triphenylphosphine) palladium(0) / H2O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH2Cl2 / 0.5 h / -78 °C 3: 89.7 percent / BBr3 / CH2Cl2 / 6 h / 20 °C 4: 53 percent / K2CO3 / acetone; ethanol / 2 h / Heating
  • 11
  • [ 156642-03-4 ]
  • [ 943024-37-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 51 percent / Na2CO3 / tetrakis(triphenylphosphine) palladium(0) / H2O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH2Cl2 / 0.5 h / -78 °C 3: 89.7 percent / BBr3 / CH2Cl2 / 6 h / 20 °C 4: 53 percent / K2CO3 / acetone; ethanol / 2 h / Heating 5: 73 percent / K2CO3 / acetonitrile / 12 h / Heating
  • 12
  • [ 156642-03-4 ]
  • [ 943024-32-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 51 percent / Na2CO3 / tetrakis(triphenylphosphine) palladium(0) / H2O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH2Cl2 / 0.5 h / -78 °C
  • 13
  • [ 156642-03-4 ]
  • [ 943024-33-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 51 percent / Na2CO3 / tetrakis(triphenylphosphine) palladium(0) / H2O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH2Cl2 / 0.5 h / -78 °C 3: 89.7 percent / BBr3 / CH2Cl2 / 6 h / 20 °C
  • 14
  • [ 156642-03-4 ]
  • [ 943024-34-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 51 percent / Na2CO3 / tetrakis(triphenylphosphine) palladium(0) / H2O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH2Cl2 / 0.5 h / -78 °C 3: 89.7 percent / BBr3 / CH2Cl2 / 6 h / 20 °C 4: 56 percent / K2CO3 / acetonitrile / 12 h / Heating
  • 15
  • [ 156642-03-4 ]
  • [ 250279-14-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2: BBr3 / CH2Cl2 / 10 h / 20 °C
  • 16
  • [ 156642-03-4 ]
  • [ 250342-77-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: NaBH4 / trifluoroacetic acid
  • 17
  • [ 156642-03-4 ]
  • [ 1027522-49-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C
  • 18
  • [ 156642-03-4 ]
  • 4'-[2-(1-hydroxy-butyl)-benzo[<i>b</i>]thiophen-3-yl]-biphenyl-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C
  • 19
  • [ 156642-03-4 ]
  • [ 250279-17-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C
  • 20
  • [ 156642-03-4 ]
  • [ 250342-71-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C
  • 21
  • [ 156642-03-4 ]
  • [ 250279-15-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C
  • 22
  • [ 156642-03-4 ]
  • [3-(4'-hydroxy-biphenyl-4-yl)-benzo[<i>b</i>]thiophen-2-yl]-thiazol-2-yl-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C
  • 23
  • [ 156642-03-4 ]
  • [3-(4'-hydroxy-biphenyl-4-yl)-benzo[<i>b</i>]thiophen-2-yl]-pyridin-2-yl-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C
  • 24
  • [ 156642-03-4 ]
  • [ 1028287-70-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C
  • 25
  • [ 156642-03-4 ]
  • [ 1026551-97-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C
  • 26
  • [ 156642-03-4 ]
  • [3-(4'-hydroxy-biphenyl-4-yl)-benzo[<i>b</i>]thiophen-2-yl]-(4-methoxy-phenyl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C
  • 27
  • [ 156642-03-4 ]
  • (4-fluoro-phenyl)-[3-(4'-hydroxy-biphenyl-4-yl)-benzo[<i>b</i>]thiophen-2-yl]-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C
  • 28
  • [ 156642-03-4 ]
  • 4'-[2-(4-hydroxy-benzyl)-benzo[<i>b</i>]thiophen-3-yl]-biphenyl-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C
  • 29
  • [ 156642-03-4 ]
  • [ 250279-18-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C
  • 30
  • [ 156642-03-4 ]
  • [3-(4'-hydroxy-biphenyl-4-yl)-benzo[<i>b</i>]thiophen-2-yl]-(4-hydroxy-phenyl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C
  • 31
  • [ 156642-03-4 ]
  • [ 250279-19-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C
  • 32
  • [ 156642-03-4 ]
  • [ 250342-78-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C
  • 33
  • [ 156642-03-4 ]
  • [ 1027835-70-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C
  • 34
  • [ 156642-03-4 ]
  • (3,4-dimethoxy-phenyl)-[3-(4'-hydroxy-biphenyl-4-yl)-benzo[<i>b</i>]thiophen-2-yl]-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C
  • 35
  • [ 156642-03-4 ]
  • [ 263759-77-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C
  • 36
  • [ 156642-03-4 ]
  • (2,4-dimethoxy-phenyl)-[3-(4'-hydroxy-biphenyl-4-yl)-benzo[<i>b</i>]thiophen-2-yl]-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C
  • 37
  • [ 156642-03-4 ]
  • [ 250342-68-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C
  • 38
  • [ 156642-03-4 ]
  • (2,4-dihydroxy-phenyl)-[3-(4'-hydroxy-biphenyl-4-yl)-benzo[<i>b</i>]thiophen-2-yl]-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C
  • 39
  • [ 156642-03-4 ]
  • [ 1027544-57-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: (dppf)PdCl2; K2CO3 / 1,2-dimethoxy-ethane
  • 40
  • [ 156642-03-4 ]
  • (2,2-dimethyl-benzo[1,3]dioxol-5-yl)-[3-(4'-hydroxy-biphenyl-4-yl)-benzo[<i>b</i>]thiophen-2-yl]-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C
  • 41
  • [ 156642-03-4 ]
  • [4'-(2-benzyl-benzo[b]thiophene-3-yl)-3-bromo-biphenyl-4-yloxy]-acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: K2CO3 / dimethylformamide / 2 h / 75 °C 7.1: NaOH / methanol; tetrahydrofuran / 0.5 h
  • 42
  • [ 156642-03-4 ]
  • [ 1026370-42-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: K2CO3 / dimethylformamide / 2 h / 75 °C
  • 43
  • [ 156642-03-4 ]
  • [ 250342-80-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: (dppf)PdCl2; K2CO3 / 1,2-dimethoxy-ethane
  • 44
  • [ 156642-03-4 ]
  • [ 250342-81-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: (dppf)PdCl2; K2CO3 / 1,2-dimethoxy-ethane
  • 45
  • [ 156642-03-4 ]
  • [4'-(2-butyl-benzo[<i>b</i>]thiophen-3-yl)-biphenyl-4-yloxy]-phenyl-acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: NaBH4 / trifluoroacetic acid 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C 6.1: NaOH / methanol; tetrahydrofuran / 1 h
  • 46
  • [ 156642-03-4 ]
  • [ 1027205-44-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: NaBH4 / trifluoroacetic acid 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C
  • 47
  • [ 156642-03-4 ]
  • [4'-(2-benzyl-benzo[b]thiophene-3-yl)-3,5-dibromo-biphenyl-4-yloxy]-acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: K2CO3 / dimethylformamide / 2 h / 75 °C 7.1: NaOH / methanol; tetrahydrofuran / 0.5 h
  • 48
  • [ 156642-03-4 ]
  • [ 1027075-31-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: (dppf)PdCl2; K2CO3 / 1,2-dimethoxy-ethane
  • 49
  • [ 156642-03-4 ]
  • 2-[4'-(2-butyl-benzo[<i>b</i>]thiophen-3-yl)-biphenyl-4-yloxy]-3-phenyl-propionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: NaBH4 / trifluoroacetic acid 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C
  • 50
  • [ 156642-03-4 ]
  • 2-[4'-(2-butyl-benzo[<i>b</i>]thiophen-3-yl)-biphenyl-4-yloxy]-3-phenyl-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: NaBH4 / trifluoroacetic acid 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C 6.1: NaOH / methanol; tetrahydrofuran / 1 h
  • 51
  • [ 156642-03-4 ]
  • [ 1027387-36-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: K2CO3 / dimethylformamide / 2 h / 75 °C
  • 52
  • [ 156642-03-4 ]
  • [ 1026491-27-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: (dppf)PdCl2; K2CO3 / 1,2-dimethoxy-ethane
  • 53
  • [ 156642-03-4 ]
  • 2-[4'-(2-benzyl-benzo[<i>b</i>]thiophen-3-yl)-biphenyl-4-yloxy]-3-phenyl-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C 6.1: NaOH / methanol; tetrahydrofuran / 1 h
  • 54
  • [ 156642-03-4 ]
  • [4-(2-benzyl-benzo[<i>b</i>]thiophen-3-yl)-[1,1';3',1'']terphenyl-4'-yloxy]-acetic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: (dppf)PdCl2; K2CO3 / 1,2-dimethoxy-ethane 7.1: K2CO3 / dimethylformamide / 2 h / 75 °C
  • 55
  • [ 156642-03-4 ]
  • [ 1026327-81-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C
  • 56
  • [ 156642-03-4 ]
  • 3-phenyl-2-[4'-(2-thiazol-2-ylmethyl-benzo[<i>b</i>]thiophen-3-yl)-biphenyl-4-yloxy]-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C 6.1: NaOH / methanol; tetrahydrofuran / 1 h
  • 57
  • [ 156642-03-4 ]
  • [ 1026748-64-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C
  • 58
  • [ 156642-03-4 ]
  • 3-phenyl-2-[4'-(2-thiazol-2-ylmethyl-benzo[<i>b</i>]thiophen-3-yl)-biphenyl-4-yloxy]-propionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C
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