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[ CAS No. 938-40-9 ] {[proInfo.proName]}

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Chemical Structure| 938-40-9
Chemical Structure| 938-40-9
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 938-40-9 ]

CAS No. :938-40-9 MDL No. :MFCD00463529
Formula : C9H5BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 225.04 Pubchem ID :-
Synonyms :

Safety of [ 938-40-9 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 938-40-9 ]

* 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 [ 938-40-9 ]

[ 938-40-9 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 4334-87-6 ]
  • [ 938-40-9 ]
  • 4-(3-ethoxycarbonylphenyl)-2H-benzopyran-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With sodium carbonate; In tetrahydrofuran; for 3h;Reflux; 4.5.1 4-(3-Ethoxycarbonylphenyl)-2H-benzopyran-2-one 4g In a 30 mL Schlenk tube equipped with a magnetic stirring bar, complex 1 (5.0 mol %), 4-bromocoumarin (1 mmol) were taken in THF (2 mL) and Na2CO3 solution (2.0 M, 1 mL). The solutions were degassed (three freeze-thaw cycles) and stirred for 10 min. After this time period, to the solution 3-ethoxycarbonylphenyl boronic acid (1 mmol) was added and the mixtures degassed. The reaction mixtures were refluxed for 3.0 h. The reactions were monitored by TLC. The reaction mixtures were then evaporated in vacuo. The resultant residues were purified by flash chromatography (silica gel) to afford the desired product as a colourless solid. Rf 0.34 (E.A 10%/PE 90%); 249 mg, 85%. Mp 123-124 C; IR (KBr, cm-1): 3054, 1726, 1702, 1608, 1302, 1166, 1030, 747; 1H NMR (300 MHz, DMSO-d6) delta=8.12-8.16 (m, 1H, Ar-H), 8.05 (s, 1H, Ar-H), 7.43-7.54 (m, 2H, Ar-H), 7.31-7.38 (m, 2H, Ar-H), 7.15-7.26 (m, 2H, Ar-H), 6.34 (s, 1H, CH), 4.32 (q, J=7.4 Hz, 2H, OCH2), 1.34 (t, J=7.6 Hz, 3H, CH3); 13C NMR (75 MHz, DMSO-d6) delta=165.9 (Cq), 160.6 (Cq), 154.8 (Cq), 154.2 (Cq), 135.4 (Cq), 132.6 (CH), 132.2 (CH), 131.3 (Cq), 130.7 (CH), 129.5 (CH), 129.4 (CH), 126.7 (CH), 124.4 (CH), 118.8 (Cq), 117.5 (CH), 115.6 (CH), 61.5 (OCH2), 14.3 (CH3). MS (ESI) m/z (relative intensity) 295 (100, M+H+); HRMS (ESI, quadrapole): m/z calcd for C18H14O4+H+ 295.0970; found 295.0968. Anal. Calcd for C18H14O4: C, 73.46; H, 4.79. Found: C, 73.45; H, 4.80%.
Reference： [1]Tetrahedron,2013,vol. 69,p. 1446 - 1453
  • 2
  • [ 938-40-9 ]
  • [ 94-09-7 ]
  • ethyl 4-[(2-oxo-2H-chromen-4-yl)amino]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With palladium diacetate; potassium carbonate; triphenylphosphine In toluene at 80℃; for 6h; Inert atmosphere; 4-(Phenylamino)-2H-chromen-2-one (3a); Typical Procedures fo r Methods A, B General procedure: Method A: 4-Bromocoumarin (1, 0.5 g, 2.22 mmol), aniline (2a, 0.81mL, 0.828 g, 8.89 mmol), and water (5 mL) were added to a flask suitable for a microwave oven. The mixture was irradiated at 100 °C for 15 min. The resulted solution was acidified with 1 M HCl. The precipitated solid was filtered under vacuum, washed with water (2 × 5 mL)and Et2O (2 × 5 mL) and dried to afford compound 3a (0.521 g, 99%). Method B: In a 20-mL round-bottom flask were placed 4-bromocoumarin (1, 0.2 g, 0.89 mmol) in toluene (2 mL) under an argon atmosphere. Aniline (2a, 0.09 mL, 92 mg, 0.99 mmol), Pd(OAc)2 (6 mg,0.027 mmol), PPh3 (14 mg, 0.054 mmol), and K2CO3 (0.368 g, 2.67mmol) were then added and the mixture was heated at 80 °C for 30 min. After cooling, it was filtered and washed with 1 M HCl (3 × 5 mL), water (2 × 5 mL), and Et2O (5 mL) and dried to give 3a (0.208 g, 99%)as a white solid; mp 267-268 °C (EtOH) (Lit.14a 268 °C).
Reference： [1]Balalas, Thomas; Abdul-Sada, Alaa; Hadjipavlou-Litina, Dimitra J.; Litinas, Konstantinos E. [Synthesis, 2017, vol. 49, # 11, p. 2575 - 2583]
  • 3
  • [ 3470-49-3 ]
  • [ 938-40-9 ]
  • 4-(1-oxo-2,3-dihydro-1H-inden-5-yloxy)-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% A mixture of 300 mg 5-hydroxyindanone(8, 2.02 mmol) and 550 mg K2CO3 (4.04 mmol) in 60 cm3of dry acetonitrile was stirred for 30 min at room temperature.Bromocoumarin 10a (460 mg, 2.02 mmol) wasadded in one portion and the reaction mixture was refluxedfor 10 h. After cooling to room temperature, 70 g of icewas added to the mixture. The brown precipitate was collected,washed well with water, dried, and recrystallisedfrom acetone to give 420 mg (71%) of 11a as yellow solid.M.p.: 162-164 C (acetone); 1H NMR (300 MHz, CDCl3):d = 2.79 (t, 2H, Ar-CH2-CH2-CO), 3.21 (t, 2H, Ar-CH2-CH2-CO), 5.48 (s, 1H, H-3), 7.21 (dd, J = 8.3 Hz, 2.0 Hz,1H, H-60), 7.31 (d, J = 2.0 Hz, 1H, H-40), 7.34-7.43 (m,2H, H-6, H-8), 7.65 (ddd, J = 8.6 Hz, 7.3 Hz, 1.5 Hz, 1H,H-7), 7.89 (d, J = 8.3 Hz, 1H, H-70), 8.01 (dd, J = 7.9 Hz,1.5 Hz, 1H, H-5) ppm; 13C NMR (75 MHz, CDCl3):d = 25.86, 36.44, 94.41, 115.11, 117.01, 119.27, 120.95,122.99, 124.29, 126.16, 133.12, 135.56, 153.71, 157.57,157.67, 162.15, 165.60, 204.91 ppm; IR (neat): m = 1703,1621, 1605, 1262, 1231, 1180 cm-1.
Reference： [1]Monatshefte fur Chemie,2018,vol. 149,p. 1787 - 1794
  • 4
  • [ 14791-78-7 ]
  • [ 938-40-9 ]
  • 4-((4-amino-3-fluorophenyl)amino)-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In ethanol; at 20 - 70℃; for 6.0h; General procedure: An appropriate amount of 2a(2b, 2c) (1.0 equiv) and p-phenylenediamineor <strong>[14791-78-7]2-fluorobenzene-1,4-diamine</strong> (1.1 equiv) were dissolved in ethanol in a oven-dried round bottom flask. Et3N (1.0equiv)was added to the reaction mixture. The reaction mixturewaskept at 70 C for 2 h and then stired at room temperature for further4 h. The crude product was recrystallized from ethanol to obtain awhite solid 3a(3b, 3c, 3d).
Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 185
  • 5
  • [ 938-40-9 ]
  • [ 23785-21-9 ]
  • 1‐(2‐oxo‐2H‐chromen‐4‐yl)‐1H‐imidazole‐4‐carboxylic acid ethylester [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With potassium carbonate In acetonitrile at 82℃; for 16h; Heating; Inert atmosphere;
Reference： [1]Simic, Milena; Petkovic, Milos; Jovanovic, Predrag; Jovanovic, Milos; Tasic, Gordana; Besu, Irina; Zizak, Zeljko; Aleksic, Ivana; Nikodinovic-Runic, Jasmina; Savic, Vladimir [Archiv der Pharmazie, 2021, vol. 354, # 11]
  • 6
  • [ 1953-54-4 ]
  • [ 938-40-9 ]
  • 4-(5-hydroxy-1H-indol-1-yl)-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
67.8% With palladium diacetate; Cs2CO3; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 130℃; for 2h; Inert atmosphere; 5.7. Synthesis of compounds 15a-15f General procedure: Intermediate 14 (1.0 mmol, 1.0 eq), Pd(OAc)2 (0.1 mmol, 0.1 eq),Xantphos (0.1 mmol, 0.1 eq), and Cs2CO3 (0.1 mmol, 0.1 eq) were addedinto 10 mL of 1,4-dioxane and then stirred at 130 C for 2 h under N2condition. Then, the mixture were concentrated under reduced pressureto give crude products, which were then purified by silica gel columnchromatography using PE/EA (3/1, v/v) as eluents to get intermediate16a-16f.
Reference： [1]Song, Jian; Guan, Yong-Feng; Liu, Wen-Bo; Song, Chun-Hong; Tian, Xin-Yi; Zhu, Ting; Fu, Xiang-Jing; Qi, Ying-Qiu; Zhang, Sai-Yang [European Journal of Medicinal Chemistry, 2022, vol. 238]

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