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Chemical Structure| 32340-38-8

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Product Details of [ 32340-38-8 ]

CAS No. :32340-38-8
Formula : C15H10O2
M.W : 222.24
SMILES Code : O=C(O)C#CC1=CC=C(C2=CC=CC=C2)C=C1
MDL No. :MFCD21013408
Boiling Point : No data available
InChI Key :MVYPVLFGHHYWMI-UHFFFAOYSA-N
Pubchem ID :65454184

Safety of [ 32340-38-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 32340-38-8 ]

* 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 [ 32340-38-8 ]

[ 32340-38-8 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 32340-38-8 ]
  • [ 62-53-3 ]
  • 3-Biphenyl-4-yl-propynoic acid phenylamide [ No CAS ]
  • 3
  • [ 32340-38-8 ]
  • (Z)-3-Biphenyl-4-yl-3-mercapto-N-phenyl-acrylamide [ No CAS ]
  • 4
  • [ 32340-38-8 ]
  • 5-Biphenyl-4-yl-2-phenyl-isothiazol-3-one [ No CAS ]
  • 5
  • [ 32340-38-8 ]
  • (Z)-3-Biphenyl-4-yl-3-carbamimidoylsulfanyl-N-phenyl-acrylamide; compound with toluene-4-sulfonic acid [ No CAS ]
  • 6
  • [ 32244-52-3 ]
  • [ 32340-38-8 ]
  • 7
  • [ 32244-60-3 ]
  • [ 32340-38-8 ]
  • 8
  • [ 32340-38-8 ]
  • [ 1115184-27-4 ]
  • 9
  • [ 124-38-9 ]
  • [ 29079-00-3 ]
  • [ 32340-38-8 ]
YieldReaction ConditionsOperation in experiment
92% General procedure: The terminal alkyne (1.0 mmol) was added to a mixtureof HSi(OEt)2Me (5.0 mmol) and KOtBu (1.5 mmol) in a10 mL Schlenk tube with a magnetic stirrer. The Schlenktube was evacuated and back-filled with CO2 for 3 times.After a CO2 ballon was connected, the reactor was moved toa water bath of 40 C. After being stirred for 2 h, the reactionmixture was diluted with water (30 mL), and was extractedwith CH2Cl2 (3×10 mL). The aqueous layer was acidifiedwith aqueous HCl (6 M) and then extracted with diethylether (5×20 mL). The combined organic extracts were driedover Na2SO4 and concentrated under vacuum to give the purepropiolic acid (such as compound 3-phenylpropiolic acid(3a): 98%).
88% Sequentially adding a catalyst in the reaction bottle (14.0 mg, 0.025 millimole, 5mol %), cesium carbonate (32.6 mg, 1.0 mmol), 4-ethynyl biphenyl (89.1 mg, 0.5 mmol),N,N-dimethylformamide(3 ml), into the carbon dioxide, in the 65 C, reaction under normal pressure 18 hours. Reaction cooling to room temperature, diluted with water, acidified with hydrochloric acid, diethyl ether extraction, washing with saturated sodium chloride for ether level, dry anhydrous sodium sulfate, obtained product is vacuum to remove the solvent, the yield is 88%.
86% With caesium carbonate; In dimethyl sulfoxide; at 60℃; for 24h;Sealed tube; Inert atmosphere; Under sealed conditions without water and oxygen, argon protection,0.6516 g of Cs2CO3 (2 mmol, 2 equiv.) was weighed into the reaction flask.A small syringe was charged with 0.1782 g (1 mmol, 1 equiv.) of 4-ethynylbiphenyl.The syringe was added with 5 mL of DMSO, and the CO 2 gas was used to displace the air in the reaction system.The reaction was carried out at 60 C for 24 h. After the reaction, the mixture was exposed to air, cooled slightly at room temperature, and then cooled in an ice water bath.Add 10 mL of deionized water, and add 20 mL of 6 mol/L HCl solution to fully acidify.The organic phase was combined and the organic phase was washed with brine brine.The organic phase is separated and dried with anhydrous Na2SO4.The solvent is removed under reduced pressure to obtain the desired product.The isolated yield was 86%.
83% With caesium carbonate; In dimethyl sulfoxide; at 60℃; under 760.051 Torr; for 24h; Add 4 ml of dimethyl sulfoxide, 1 mmol of 4-ethynylbiphenyl, 2 mmol of cesium carbonate into the reaction tube,The reaction tube was pumped and ventilated 3 times, and filled with CO2. After the CO2 was filled, the gas pressure of the reaction tube was 1 atm. The reaction tube was stirred for 24 hours under the conditions of carbon dioxide atmosphere and 60C. The stirring rate is 800 rpm, stop stirring, and cool to room temperature.Add water to the reaction solution, extract 4 times with ethyl acetate, separate the layers, take the aqueous layer, acidify the aqueous layer with 2 moles of hydrochloric acid per liter to pH=1, then extract with ethyl acetate, take the organic layer, and wash the organic layer with saturated brine It was dried over magnesium sulfate, the filtrate was filtered, and concentrated under reduced pressure to obtain the target product with a yield of 83%.

  • 10
  • [ 32340-38-8 ]
  • [ 1372715-37-1 ]
  • 11
  • [ 32340-38-8 ]
  • [ 107-18-6 ]
  • [ 1372715-25-7 ]
  • 12
  • 3-biphenyl-4-yl-2,3-dibromo-propionic acid [ No CAS ]
  • [ 32340-38-8 ]
YieldReaction ConditionsOperation in experiment
Intermediate 28; Biphenyl-4-yl-propynoic acid; 5.00 g (13.0 mmol) 3-biphenyl-4-yl-2,3-dibromo-propionic acid are added to 40 mL tBuOH. Over a period of 25 min 5.80 g (52.1 mmol) KOtBu are added in several portions while keeping the temperature below 35 C. Then the reaction mixture is stirred at 40 C. for 2 h. Again 1.40 g (12.5 mmol) potassium tert-butoxide are added and the mixture is stirred for additional 2 h at 40 C. Then the mixture is allowed to cool to r.t. and poured onto icewater/concentrated HCl. The precipitate is filtered and partitioned between EtOAc and water. The organic layer is washed with water, dried and the solvent is removed in vacuo. The crude product is triturated with PE, filtered and dried at 80 C. in vacuo.C15H10O2 (M=222.2 g/mol)ESI-MS: 223 [M+H]+ Rf (TLC): 0.4 (silica gel, DCM/MeOH/AcOH 5/1/0.01)
  • 13
  • [ 32340-38-8 ]
  • [ 1395463-00-9 ]
  • [ 1363436-46-7 ]
YieldReaction ConditionsOperation in experiment
With tetrabutyl ammonium fluoride;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium(0); In 1-methyl-pyrrolidin-2-one; at 90℃; for 3h; Example 21; N-[2-(4-Biphenyl-4-ylethynyl-phenyl)-1-methyl-ethyl]acetamide; To 0.22 g (1.00 mmol) <strong>[32340-38-8]biphenyl-4-yl-propynoic acid</strong> (I28) and 0.26 g (1.00 mmol) N-[2-(4-bromo-phenyl)-1-methyl-ethyl]-acetamide (I44.1) in 3.00 mL NMP are added 0.06 g (0.10 mmol) 1,1'-bis(diphenylphosphonino)ferrocene, 1.68 g (6.00 mmol) TBAF*H2O and 0.05 g (0.05 mmol) tris(dibenzylidenacetone)dipalladium(0). The reaction mixture is stirred at 90 C. for 3 h. The mixture is allowed to cool to r.t. and poured onto saturated aq NH4Cl solution. The precipitate is filtered, washed with water and purified by column chromatographie (silica gel; DCM/MeOH 9/1). The resulting product is triturated with isopropanol and dried at 60 C. in vacuo.C25H23NO (M=353.5 g/mol)ESI-MS: 354 [M+H]+ Rt (HPLC): 3.57 min (method B)
  • 14
  • 4-phenylcinnamic acid [ No CAS ]
  • [ 32340-38-8 ]
  • 15
  • [ 1591-31-7 ]
  • [ 471-25-0 ]
  • [ 32340-38-8 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 5h;Inert atmosphere; General procedure: Compounds (1b-1o) were prepared according to literature.17 To a mixture of Pd(PPh3)2Cl2 (70 mg, 2 mol%), CuI (38 mg, 4 mol%) and DMF (7 mL) taken in a flask, aryl iodide (5.0 mmol), propiolic acid (414 mg, 6.0 mmol) and diisopropylamine (1.30 g, 12.5 mmol) were added in that sequence under nitrogen atmosphere. After stirring the reaction mixture at room temperature for 5 h, the resulting mixture was diluted with ethyl acetate, filtered through Celite bed, the filtrate was washed with cold aqueous KOH solution (1 x 100 mL) and acidified with dilute sulfuric acid (10% solution) at 0 C. The solid obtained was extracted with dichloromethane and the extract was washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated in vacuum at 40 C, dried to get the arylpropiolic acids.
With tetrakis(triphenylphosphine) palladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 20℃; for 12h; In a reaction vessel, p-iodobiphenyl (10.0 mmol), DBU (3.66 g, 24 mmol, 2.4 equiv), Pd(PPh4)3 (288 mg, 0.26 mmol, 2.5 mol %) was dissolved in 12 ml of DMSO.Solution a was formed, then propynoic acid (840 mg, 12 mmol, 1.2 equiv) was dissolved in 12 ml of DMSO to form solution b, and finally solution b was slowly added dropwise to solution a.The reaction was allowed to stir at room temperature for 12 hours. After the reaction was completed, 25 ml of ethyl acetate was added to the reaction solution.Extract with saturated sodium bicarbonate solution, collect the aqueous layer, and adjust the pH to 2.0 with 1 mol/L hydrochloric acid.Finally, the organic layer was extracted with dichloromethane, the organic phase was separated, and the water was removed with anhydrous sodium sulfate.After drying, the solvent was distilled off under reduced pressure to obtain a crude product, and the crude product was separated by column chromatography to obtain a 3-(1,1'-biphenyl)propiolic acid compound.
With tetrakis(triphenylphosphine) palladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 35℃; for 10h;Inert atmosphere; To a 100 mL of round-bottom flask were added Pd(PPh3)4 (577.8 mg, 5 mol%), aryl iodide (10.0 mmol, 1.0 equiv), DBU (3.040 g, 20 mmol, 2.0 equiv) and DMSO (15 mL). Then the solution of propiolic acid (771 mg, 11 mmol, 1.1 equiv) in DMSO (5 mL) was added dropwise. The round-bottom flask was put into a preheated oil bath (35 C). After stirring for 10 h, the reaction mixture was cooled to room temperature. The reaction mixture was diluted with EtOAc, and extracted with saturated aqueous NaHCO3 solution. The aqueous layer was separated, acidified to pH 2.0 by cold HCl (1N), and extracted with CH2Cl2. The combined organic layers were dried with Na2SO4, filtered, and the solvent was removed under reduced pressure. The resulting crude product was purified by flash chromatography on silica gel (PE/EA = 2:1 with HOAc (1%, v/v)) to give 1b-1q.
  • 16
  • [ 32340-38-8 ]
  • [ 124-02-7 ]
  • [ 1443420-98-1 ]
  • 17
  • [ 887144-94-7 ]
  • [ 32340-38-8 ]
  • [ 1094416-25-7 ]
  • 18
  • [ 32340-38-8 ]
  • [ 4381-25-3 ]
  • [ 1498210-68-6 ]
  • 19
  • [ 32340-38-8 ]
  • [ 29079-15-0 ]
YieldReaction ConditionsOperation in experiment
92% With copper(l) iodide; iodine; potassium carbonate; In dimethyl sulfoxide; at 50℃; for 24h;Inert atmosphere; General procedure: 4.2 General procedure for the CuI-catalyzed decarboxylative homocoupling reaction: A mixture of aryl propiolic acid (0.2 mmol), CuI (30 mol %), I2 (55 mol %), and K2CO3 (0.4 mmol) in 2 mL DMSO was stirred at 50 C under N2 for 24 h. Then 5 mL of ethyl acetate was added. The mixture was filtered through the diatomite under reduced pressure, and the filtration was washed with ethyl acetate. The filtrate was washed with saturated Na2S2O3, saturated brine, and was dried over Na2SO4. The solvent was removed under reduced pressure. The crude product was purified by flash silica gel column chromatography.
  • 20
  • [ 353-83-3 ]
  • [ 32340-38-8 ]
  • [ 1421680-91-2 ]
  • 21
  • [ 50-00-0 ]
  • [ 32340-38-8 ]
  • [ 100-46-9 ]
  • [ 98-80-6 ]
  • [ 1084799-73-4 ]
  • 22
  • [ 32340-38-8 ]
  • [ 100-61-8 ]
  • 3-([1,1'-biphenyl]-4-yl)-N-methyl-N-phenylpropiolamide [ No CAS ]
  • 23
  • [ 32340-38-8 ]
  • [ 100-61-8 ]
  • 4-([1,1'-biphenyl]-4-yl)-1-methyl-3-(trifluoromethyl)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione [ No CAS ]
  • 24
  • [ 110-91-8 ]
  • [ 201230-82-2 ]
  • [ 32340-38-8 ]
  • 3-(biphenyl-4-yl)-1-morpholinoprop-2-yn-1-one [ No CAS ]
  • 25
  • [ 32340-38-8 ]
  • [ 762-04-9 ]
  • [ 42516-23-4 ]
  • 26
  • [ 32340-38-8 ]
  • [ 4559-70-0 ]
  • 1-([1,1'-biphenyl]-4-yl)-2-(diphenylphosphoryl)ethan-1-one [ No CAS ]
  • 27
  • [ 32340-38-8 ]
  • [ 98-80-6 ]
  • [ 36803-53-9 ]
  • 28
  • [ 32340-38-8 ]
  • [ 4559-70-0 ]
  • 3-([1,1′-biphenyl]-4-yl)-2-(diphenylphosphoryl)-1-phenyl-1H-phosphindole 1-oxide [ No CAS ]
  • 29
  • [ 50-00-0 ]
  • [ 32340-38-8 ]
  • [ 156-87-6 ]
  • 3-(3-([1,1'-biphenyl]-4-yl)prop-2-yn-1-yl)-1,3-oxazinane [ No CAS ]
  • 30
  • [ 50-00-0 ]
  • [ 32340-38-8 ]
  • [ 20989-17-7 ]
  • (S)-3-(3-([1,1'-biphenyl]-4-yl)prop-2-yn-1-yl)-4-phenyloxazolidine [ No CAS ]
  • 31
  • [ 32340-38-8 ]
  • [ 73183-34-3 ]
  • (E)-2-(2-([1,1'-biphenyl]-4-yl)vinyl-1,2-D2)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • 32
  • [ 50-00-0 ]
  • [ 32340-38-8 ]
  • 4-(propa-1,2-dien-1-yl)-1,1’-biphenyl [ No CAS ]
  • 33
  • [ 92-66-0 ]
  • [ 471-25-0 ]
  • [ 32340-38-8 ]
  • 34
  • [ 32340-38-8 ]
  • [ 73183-34-3 ]
  • [ 941666-88-2 ]
YieldReaction ConditionsOperation in experiment
75% With copper(l) iodide; lithium methanolate; bis[2-(diphenylphosphino)phenyl] ether; In dimethyl sulfoxide; at 50℃; for 16h; General procedure: Phenylpropiolic acid (439 mg, 3.0 mmol), B2pin2 (763 mg, 3.0 mmol), lithium methoxide (23 mg, 0.6 mmol), copper iodide (57 mg, 0.3 mmol), and Dpe-Phos (324 mg, 0.6 mmol) were added to a vial containing DMSO (5 mL). The suspension was stirred for 16 h at 50 C. The reaction was monitored by TLC, and after the completion of the reaction, the reaction mass was cooled to 25-28 C and quenched into a mixture of 50 mL of water and 50 mL of ethyl acetate. The ethyl acetate layer was washed with water (2 × 25 mL), brine (2 × 25 mL), and then dried over Na2SO4. Evaporation of the solvent under reduced pressure provided the crude product, which was purified by column chromatography (hexane:EtOAc = 9.5:0.5).
67% With copper(II) trifluoroacetate; sodium carbonate; In 1,4-dioxane; at 80℃; for 18h;Inert atmosphere; General procedure: A Schlenk tube with a magnetic stirring bar was charged with 3-phenylpropiolic acid (1a, 68 mg, 0.5 mmol), bis(pinacolato)diboron (2a, 152 mg, 0.6 mmol), Cu(TFA)2 (29 mg, 10 mol%), Na2CO3 (127 mg, 1.2 mmol), and 1,4-dioxane (2 mL) under N2. The reaction mixture was stirred at 80 C for 18 h (monitored by TLC and GC). Upon completion of the reaction, the reaction mixture was then cooled to ambient temperature, diluted with ethyl acetate (20 mL), filtered through a plug of silica gel, and washed with ethyl acetate (20 mL). The organic layer was washed with saturated brine (20 mL×2) and dried over anhydrous Na2SO4. The solvents were removed via rotary evaporator and the residue was purified by flash chromatography (silica gel, ethyl acetate: petroleum ether=1:30) to give 89.7 mg of desired product 3a in 78 % yield as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.48-7.50 (m, 2H), 7.41 (d, 1H, J=18.5Hz), 7.29-7.32 (m, 3H), 6.18 (d, 1H, J=18.4Hz), 1.32 (s, 12H). 13C NMR (100 MHz, CDCl3): δ 148.5, 136.4, 127.9, 127.5, 126.0, 82.3, 23.8
  • 35
  • [ 32340-38-8 ]
  • [ 81290-20-2 ]
  • 4-(3,3,3-trifluoroprop-1-yn-1-yl)-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% General procedure: A mixture of CuI (76 mg, 0.4 mmol), phen (79 mg, 0.4 mmol), Ag2CO3 (220 mg, 0.8 mmol), KF (69 mg, 1.2 mmol) and DMF (6 mL) was added to a 25 mL round-bottom flask that was equipped with a magnetic stir bar at room temperature in a glove box. The round bottom flask was sealed with a rubber plug and taken out. Then the flask was evacuated and refilled with nitrogen for three times. Next, Me3SiCF3 (294 mL, 2.0 mmol) was added to the mixture dropwise in 5 min and the mixture was stirred at room temperature for 30 min. A solution of arylpropiolic acids (0.4 mmol) in 1.0 mL DMF was added to the flask during 4 h by using a syringe pump at room temperature. After the addition, the reaction mixture was kept for another 2 h at room temperature. At the end of reaction, dichloromethane (DCM) was added to the reaction system. The organic layer was separated and washed with water three times. The combined organic extracts was dried over Na2SO4 for 2 h and then concentrated under vacuum. After evaporation, the residue was purified by silica gel column chromatography with petroleum ether to provide pure desired products.
 

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