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Chemical Structure| 94569-84-3 Chemical Structure| 94569-84-3

Structure of 94569-84-3

Chemical Structure| 94569-84-3

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Product Details of [ 94569-84-3 ]

CAS No. :94569-84-3
Formula : C7H4BrFO
M.W : 203.01
SMILES Code : C1=C(C(=CC=C1F)Br)C=O
MDL No. :MFCD00142872
InChI Key :CJUCIKJLMFVWIS-UHFFFAOYSA-N
Pubchem ID :2773321

Safety of [ 94569-84-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 94569-84-3 ]

* 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 [ 94569-84-3 ]

[ 94569-84-3 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 94569-84-3 ]
  • [ 536-74-3 ]
  • [ 943835-77-6 ]
YieldReaction ConditionsOperation in experiment
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine; In tetrahydrofuran; at 50℃; for 4h;Inert atmosphere; General procedure: A two-necked dry flask was charged with the ortho-bromobenzaldehyde (10 mmol), the ethynylbenzene (1.22 g, 12 mmol), and freshly distilled THF 20 mL. Then Et3N (2.8 mL, 20 mmol, 2.0 equiv), PdCl2(PPh3)2 (210 mg, 0.36 mmol, 0.03 equiv), and CuI (95.2 mg, 0.6 mmol, 0.05 equiv) were added. The mixture was heated at 50 C for 4 h. After the reaction was complete (monitored by TLC), the solvents were evaporated under reduced pressure. The crude product was purified by column chromatography (SiO2, ethyl acetate/petroleum ether = 100: 1) to afford the ortho-alkynylbenzaldehyde.
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine; at 55℃;Inert atmosphere; General procedure: To a solution of 2-bromobenzaldehyde (1.85 g, 10.0 mmol) and ethynylbenzene (1.124g,11.0 mmol) in Et3N (20.0 mL) was added Pd(PPh3)2Cl2 (140 mg, 2.0% mol) and CuI (20 mg,1.0% mol). The mixture was stirred at 55 oC for overnight. It was then quenched with water andwashed with ethyl acetate. After removal of solvent, the crude residue was purified by flashchromatography on silica gel (petroleum ether/ethyl acetate = 100:1, v/v) to afford the desiredproduct 2-(phenylethynyl)benzaldehyde (2.02 g, 98% yield).
References: [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1755 - 1761.
[2]Advanced Synthesis and Catalysis,2016,vol. 358,p. 2684 - 2691.
[3]Chemical Communications,2012,vol. 48,p. 7634 - 7636.
[4]Journal of Organic Chemistry,2008,vol. 73,p. 5135 - 5138.
[5]Angewandte Chemie - International Edition,2017,vol. 56,p. 10928 - 10932.
    Angew. Chem.,2017,vol. 129,p. 11068 - 11072.
[6]Chemistry - A European Journal,2014,vol. 20,p. 3917 - 3921.
[7]ACS Combinatorial Science,2011,vol. 13,p. 265 - 271.
[8]Organic Letters,2011,vol. 13,p. 2228 - 2231.
[9]Synthesis,2013,vol. 45,p. 1553 - 1563.
[10]Tetrahedron Letters,2009,vol. 50,p. 4167 - 4169.
[11]Organic Letters,2014,vol. 16,p. 5926 - 5929.
[12]Chemistry - A European Journal,2015,vol. 21,p. 14401 - 14409.
[13]Chemistry - A European Journal,2019,vol. 25,p. 9385 - 9389.
[14]Chemistry - A European Journal,2015,vol. 21,p. 18122 - 18127.
[15]Organic Letters,2016,vol. 18,p. 5150 - 5153.
[16]Organic Letters,2016,vol. 18,p. 5612 - 5615.
[17]Advanced Synthesis and Catalysis,2011,vol. 353,p. 392 - 400.
[18]Chemistry - A European Journal,2011,vol. 17,p. 13409 - 13414.
[19]Journal of Organic Chemistry,2007,vol. 72,p. 4462 - 4468.
[20]Angewandte Chemie - International Edition,2010,vol. 49,p. 4633 - 4637.
[21]Chemical Communications,2010,vol. 46,p. 7427 - 7429.
[22]Organic Letters,2011,vol. 13,p. 640 - 643.
[23]Chemistry - A European Journal,2011,vol. 17,p. 4981 - 4985.
[24]Tetrahedron,2012,vol. 68,p. 5263 - 5268.
[25]Angewandte Chemie - International Edition,2012,vol. 51,p. 10861 - 10865.
    Angew. Chem.,2012,vol. 124,p. 11019 - 11023.
[26]Molecules,2013,vol. 18,p. 814 - 831.
[27]Chemistry - A European Journal,2013,vol. 19,p. 4695 - 4700.
[28]Advanced Synthesis and Catalysis,2013,vol. 355,p. 559 - 568.
[29]Journal of the American Chemical Society,2015,vol. 137,p. 1165 - 1180.
[30]Journal of Organic Chemistry,2015,vol. 80,p. 7635 - 7641.
[31]Advanced Synthesis and Catalysis,2015,vol. 357,p. 3255 - 3261.
[32]Journal of Organic Chemistry,2014,vol. 79,p. 10674 - 10681.
[33]Chemistry - A European Journal,2016,vol. 22,p. 9125 - 9129.
[34]Angewandte Chemie - International Edition,2016,vol. 55,p. 11882 - 11886.
    Angew. Chem.,2016,vol. 128,p. 12061 - 12065.
[35]Organic Letters,2017,vol. 19,p. 5070 - 5073.
[36]Organic Letters,2017,vol. 19,p. 5856 - 5859.
[37]Organic and Biomolecular Chemistry,2018,vol. 16,p. 9147 - 9151.
[38]Advanced Synthesis and Catalysis,2019.
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[40]Organic Letters,2019,vol. 21,p. 3696 - 3700.
[41]Organic Letters,2020,vol. 22,p. 3890 - 3894.
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[43]Journal of Organic Chemistry,2021,vol. 86,p. 333 - 351.
[44]Journal of Organic Chemistry,2021,vol. 86,p. 3758 - 3767.
[45]Advanced Synthesis and Catalysis,2021,vol. 363,p. 2664 - 2669.
[46]Advanced Synthesis and Catalysis,2021,vol. 363,p. 2834 - 2842.
[47]Organic and Biomolecular Chemistry,2021,vol. 19,p. 6657 - 6664.
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[49]Chinese Chemical Letters,2022.
  • 3
  • [ 20197-92-6 ]
  • [ 94569-84-3 ]
  • [ 107-11-9 ]
  • C19H15FN2O3 [ No CAS ]
  • 4
  • [ 3325-11-9 ]
  • [ 126-81-8 ]
  • [ 94569-84-3 ]
  • 2-fluoro-12,12-dimethyl-12,13-dihydroquinolino[4,3,2-mn][1,2,3]triazolo[4,5,1-de]acridin-14(11H)-one [ No CAS ]
  • 5
  • [ 4341-24-6 ]
  • [ 3325-11-9 ]
  • [ 94569-84-3 ]
  • 2-fluoro-12-methyl-12,13-dihydroquinolino[4,3,2-mn][1,2,3]triazolo[4,5,1-de]acridin-14(11H)-one [ No CAS ]
  • 6
  • [ 3325-11-9 ]
  • [ 504-02-9 ]
  • [ 94569-84-3 ]
  • 2-fluoro-12,13-dihydroquinolino[4,3,2-mn][1,2,3]triazolo[4,5,1-de]acridin-14(11H)-one [ No CAS ]
  • 7
  • [ 94569-84-3 ]
  • [ 13214-64-7 ]
  • 4-(2-bromo-5-fluorobenzylidene)-2-(4-methoxyphenyl)-1,3-oxazol-5(4H)-one [ No CAS ]
  • 8
  • [ 94569-84-3 ]
  • [ 747392-34-3 ]
  • 9
  • [ 57134-53-9 ]
  • [ 94569-84-3 ]
  • [ 943835-77-6 ]
  • 10
  • [ 32566-01-1 ]
  • [ 94569-84-3 ]
  • C21H14BrFN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide; at 70℃; for 10h;Inert atmosphere; Schlenk technique; General procedure: To a schlenk tube (15 mL) containing a solution of <strong>[32566-01-1]2-(1H-indol-2-yl)aniline</strong> 3a (0.4 mmol) in DMSO (2 mL) was added 2-bromobenzaldehyde 4 (0.44 mmol) under nitrogen atmosphere.Then, the reaction mixture was stirred at 70C for 10 h until <strong>[32566-01-1]2-(1H-indol-2-yl)aniline</strong> 3a was consumed completely. Next, Pd(PPh3)2Cl2(0.02 mmol), [(t-Bu)3PH]BF4 (0.06 mmol) and Et3N (1.2 mmol) wereadded into the above reaction system under CO (1 atm) atmo-sphere. After being stirred at 120C for 5 h, the resulting mixturewas quenched with NH4Cl and extracted with ethyl acetate. Thecombined organic layer was washed with H2O and brine, and thendried over anhydrous Na2SO4. The solvent was removed underreduced pressure and the residue was puried by column chro-matography on silica gel (petroleum ether/ethyl acetate 5:1) toafford the corresponding indolo[1,2-c]isoindolo[2,1-a]quinazolin-5(16aH)-one 2.
  • 11
  • [ 15666-97-4 ]
  • [ 94569-84-3 ]
  • octyl 3-amino-4-cyano-7-fluoro-2-naphthoate [ No CAS ]
  • 12
  • [ 16155-03-6 ]
  • [ 94569-84-3 ]
  • 2-(2-bromo-5-fluorobenzyl)-4-methyl-1-(4-nitrophenyl)piperazine [ No CAS ]
 

Historical Records

Technical Information

• Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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