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Product Details of [ 52188-06-4 ]

CAS No. :52188-06-4 MDL No. :MFCD07772989
Formula : C12H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FHWHJXFPGFXZEG-UHFFFAOYSA-N
M.W : 188.22 Pubchem ID :12549560
Synonyms :

Safety of [ 52188-06-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52188-06-4 ]

* 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 [ 52188-06-4 ]

[ 52188-06-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 5720-05-8 ]
  • [ 623-47-2 ]
  • [ 52188-06-4 ]
YieldReaction ConditionsOperation in experiment
84% With C32H28BrFeIN3Pd; anhydrous potassium acetate; silver(I) oxide In 1,2-dichloro-ethane at 80℃; for 24h;
83% With C32H26FeIN2PPd; anhydrous potassium acetate; silver(I) oxide In dichloromethane at 25℃; for 24h; General Procedure for the Coupling of Terminal AlkynesWith Arylboronic Acids General procedure: A mixture of arylboronic acids (0.5 mmol), alkynes(0.6 mmol), the prescribed amount of catalysts, Ag2O(0.5 mmol), and KOAc (0.75 mmol) in 1,2-dichloroethane(DCE) (3 mL) under air was stirred at 80 or 25Cfor24 h. After being cooled, the mixture wasfiltered. The solvent was removed under reduced pressure. The resultingresidue was purified byflash chromatography on silica gelto afford the desired coupled products, which were characterized by comparing their m.p. and1HNMRspectra.
74% With copper (I) iodide; air; Cs2CO3; silver(I) oxide In dichloromethane at 80℃; for 36h;
42% With copper (I) iodide; Cs2CO3; silver(I) oxide In 1,2-dichloro-ethane at 80℃; for 36h; Sealed tube;
With copper (I) iodide; palladium diacetate; Cs2CO3; anhydrous silver carbonate In DCE at 80℃; for 24h;
With copper (I) iodide; Cs2CO3; silver(I) oxide In 1,2-dichloro-ethane at 80℃; for 36h;

  • 2
  • [ 52188-06-4 ]
  • [ 529-23-7 ]
  • [ 1350934-78-9 ]
YieldReaction ConditionsOperation in experiment
91% With silver trifluoromethanesulfonate In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; General procedure for the heterogeneous Au(I)-catalyzed synthesis of quinolines General procedure: To a solution of 2-aminoaryl carbonyl 1 (0.5 mmol), MCM-41-PPh3-AuCl (128 mg, 0.05 mmol), AgOTf (12.9 mg, 0.05 mmol) in DMF (5 mL) was added internal alkyne 2 (0.75 mmol) under Ar. The reaction mixture was stirred at 100°C for 4 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (20 mL) and filtered. The gold catalyst was washed with NH3·H2O (2 × 5 mL), distilled water (5 mL), and acetone (2 × 5 mL) and reused in the next run. The filtrate was washed with water (2 × 10 mL) and brine (2 × 10 mL), and the organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate = 15/1) to afford the desired product 3.
90% With (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere;
  • 3
  • [ 52188-06-4 ]
  • [ 18358-63-9 ]
  • [ 1606982-23-3 ]
  • 4
  • [ 4294-57-9 ]
  • [ 41658-03-1 ]
  • [ 52188-06-4 ]
  • 5
  • [ 624-31-7 ]
  • [ 623-47-2 ]
  • [ 52188-06-4 ]
YieldReaction ConditionsOperation in experiment
99% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate In tetrahydrofuran for 24h; Inert atmosphere; Heating;
94% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate In 1,2-dimethoxyethane at 40℃; for 22h; Inert atmosphere; Schlenk technique; Sealed tube; 4.2. General procedure for the synthesis of ethyl arylpropiolates 3 General procedure: Bis(triphenylphosphane)palladium(II)dichloride (14.2 mg,20.0 mmol, 2.00 mol%) and copper(I) iodide (7.62 mg, 40.0 mmol,4.00 mol%) were placed in a flame-dried 10 mL Schlenk tube with amagnetic stir bar under a nitrogen atmosphere and the Schlenktube was evacuated and flushed with nitrogen two more times.DME (3.0 mL) was added and the resulting yellow solution wasstirred for several minutes at rt. Aryl iodide 1 (1.00 mmol, 1.00equiv) and potassium carbonate (276 mg, 2.00 mmol, 2.00 equiv)were added and the vessel was closed and heated to 40 °C. Ethylpropiolate (2) (198 mg, 2.00 mmol, 2.00 equiv) was dissolved inDME (0.95 mL) and added slowly over 21 h (1.0 mL syringe,0.50 mm/min feed rate). After complete addition, the syringe wasrinsed in the reaction mixture and stirring was continued for 1 h at40 °C. Celite was added to the dark brown mixture and the solventwas removed under reduced pressure. For purification, chromatographyon silica gel was performed using manual flash techniqueor a Biotage SP4 flash purification system with eluents consisting ofn-hexane and EtOAc or acetone.
62% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h;
46.7% With copper(I) oxide In N,N-dimethyl-formamide at 100℃; for 16h; Inert atmosphere; 1-3 Step 1 Add 2.00 mL of ethyl propiolate to 25 mL of dry dimethylformamide, then add 2.18 g of 4-iodotoluene to it and mix well, then add 2.86 g of Cu2O to carry out the system Three vacuum/nitrogen cycle degassing operations, and then the system was stirred and reacted at 100°C for 16h under a nitrogen atmosphere. The above dimethylformamide was 0.225mM monoisopine pinylborane and 0.445mM diisopine Pinylborane; after final purification, 878.51 mg of yellow liquid product-Ozagrel Impurity II was obtained, and the yield of the product was 46.7%.
42% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate In tetrahydrofuran at 65℃; for 12h; Inert atmosphere;
42% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate In tetrahydrofuran at 65℃; for 24h; Inert atmosphere; Schlenk technique; Synthesis of starting materials General procedure: 3-Arylpropiolates were synthesized according to the following procedure:1 To a suspension of K2CO3 (2 equiv), CuI (0.04 equiv) and [PdCl2(PPh3)2] (0.02 equiv.) in THF (15 mL), were added ethyl propiolate (4 equiv.) and the corresponding aryliodide (1 equiv.). The mixture was stirred at 65°C for 24 h, then was diluted with DCM and extracted three times with water. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford a residue, which was further purified by column chromatography using mixtures of hexane:EtOAc as eluent.
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate In tetrahydrofuran at 65℃; for 12h; Inert atmosphere;
With copper(l) iodide; potassium carbonate In tetrahydrofuran at 65℃; for 24h; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate In tetrahydrofuran at 75℃; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate In 1,2-dimethoxyethane at 40℃; for 13h; Schlenk technique; Inert atmosphere;
Stage #1: 4-tolyl iodide; propynoic acid ethyl ester With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With copper(l) iodide In tetrahydrofuran at 75℃; Inert atmosphere;

Reference: [1]Zhao, Chuan-Qi; Chen, Yue-Gang; Qiu, Hui; Wei, Lei; Fang, Ping; Mei, Tian-Sheng [Organic Letters, 2019, vol. 21, # 5, p. 1412 - 1416]
[2]Götzinger, Alissa C.; Michaelis, Carina S.; Müller, Thomas J.J. [Dyes and Pigments, 2017, vol. 143, p. 308 - 316]
[3]Wu, Yongcheng; Wu, Fuhai; Zhu, Daqian; Luo, Bingling; Wang, Haiwen; Hu, Yumin; Wen, Shijun; Huang, Peng [Organic and Biomolecular Chemistry, 2015, vol. 13, # 41, p. 10386 - 10391]
[4]Current Patent Assignee: SHENZHEN SUNGENING TECH - CN111269120, 2020, A Location in patent: Paragraph 0052-0063
[5]Fu, Liangbing; Guptill, David M.; Davies, Huw M. L. [Journal of the American Chemical Society, 2016, vol. 138, # 18, p. 5761 - 5764]
[6]Cocoletzi-Xochitiotzi, Ana Patricia; Hernández-Hernández, Miguel; Medina-Mercado, Ignacio; Jiménez-Martínez, Williams De Jesús; Mastranzo, Virginia Maricela; Porcel, Susana [Synthesis, 2020, vol. 52, # 16, p. 2379 - 2386]
[7]Li, Jing; Zhang, Jing; Tan, Haibo; Wang, David Zhigang [Organic Letters, 2015, vol. 17, # 10, p. 2522 - 2525]
[8]Li, Jun; Lin, Lili; Hu, Bowen; Zhou, Pengfei; Huang, Tianyu; Liu, Xiaohua; Feng, Xiaoming [Angewandte Chemie - International Edition, 2017, vol. 56, # 3, p. 885 - 888][Angew. Chem., 2017, vol. 129, # 3, p. 903 - 906]
[9]Zeng, Xiaojun; Lu, Zhichao; Liu, Shiwen; Hammond, Gerald B.; Xu, Bo [Advanced Synthesis and Catalysis, 2017, vol. 359, # 22, p. 4062 - 4066]
[10]Niedballa, Jonas; Reiss, Guido J.; Müller, Thomas J. J. [European Journal of Organic Chemistry, 2020, vol. 2020, # 31, p. 5019 - 5024]
[11]Xia, Xiao-Feng; Zhao, Mingming; He, Wei; Zou, Lianghua; San, Xinxin; Wang, Dawei [Advanced Synthesis and Catalysis, 2020, vol. 362, # 17, p. 3621 - 3626]
  • 6
  • [ 617-37-8 ]
  • 1-(p-tolylethynyl)-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one [ No CAS ]
  • [ 52188-06-4 ]
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