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[ CAS No. 529-28-2 ]

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Chemical Structure| 529-28-2
Chemical Structure| 529-28-2
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Product Details of [ 529-28-2 ]

CAS No. :529-28-2 MDL No. :MFCD00001039
Formula : C7H7IO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :234.03 g/mol Pubchem ID :68257
Synonyms :

Safety of [ 529-28-2 ]

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 [ 529-28-2 ]

  • Upstream synthesis route of [ 529-28-2 ]
  • Downstream synthetic route of [ 529-28-2 ]

[ 529-28-2 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 288-13-1 ]
  • [ 529-28-2 ]
  • [ 102908-37-2 ]
YieldReaction ConditionsOperation in experiment
82% With (N,N'-bis(salicylidenate)cyclohexane-1,2-diamine)copper(II); sodium hydroxide In dimethyl sulfoxide at 100℃; for 12 h; Sealed tube General procedure: Complex 2 (0.05 mmol) was added to a 5 mL of a sealed tube containing the aryl iodide or bromide (0.5 mmol), 1H-pyrazole (0.75 mmol), NaOH (1 mmol), and DMSO (1 mL). The mixture was stirred at 100 °C for 12 h. After being cooled to room temperature, the mixture was quenched with 10 mL H2O and extracted with EtOAc(3 × 20 mL). The combined EtOAc extracts were dried with anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure.The residue was purified by flash column chromatography on silicagel with PE/EtOAc (from 10:1 to 5:1) as the eluent to afford the pure products. All N-aryl pyrazoles reported here are known products and were characterised by 1H NMR, and GC-MS.
68% With bis(1-dodecylimidazole)cupronium dichlorocuprate; tetrabutylammomium bromide; potassium carbonate In water at 80℃; for 15 h; Green chemistry General procedure: At first [Cu(Im12)2]CuCl2 (0.5 mmol, 0.305 g) was added to a 25 mL round bottom flask containing water (4 mL), indole (0.117 g, 1 mmol) and iodobenzene (0.203 g, 1 mmol).K2CO3 (0.276 g, 2 mmol) and TBAB (0.322 g, 1 mmol) was added and the reaction stirred at 80 °C for 12 h. The reaction progress was monitored by TLC(EtOAc/n-hexane; 1:3 v/v) and after completion, the organic phase was extracted from the ionic liquid with EtOAc (2 8 mL) and concentrated in vacuo. The promoter was used directly for the next run. The product was purified by silica gel column chromatography (EtOAc/n-hexane; 1:3 v/v). The isolated product was dried under vacuum overnight to give a yield of 92percent. All products are known in the literature and were identified by comparison of their FT-IR, 1H, and 13C NMR spectra with the literature data.
54% With copper diacetate; sodium hydroxide; 3-(diphenylphosphino)propionic acid In 1,4-dioxane at 100℃; for 24 h; Sealed tube General procedure: Cu(OAc)2 (0.03mmol), L2 (0.06mmol), aryl idione or bromide (0.5mmol), 1H-pyrazole (0.75mmol), NaOH (1mmol), and 1,4-dioxane (1mL) was added into a 5mL tube, then sealed. The mixture was stirred at 100°C for certain time. After cooling to room temperature, the mixture was quenched with 10mL H2O and extracted with EtOAc (3×20mL). The combined EtOAc extracts were dried with anhydrous Na2SO4 and filtrated and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE/EtOAc, as the eluent, to afford the desired products.
30% With copper(l) iodide; manganese(II) fluoride; (1R,2R)-1,2-diaminocyclohexane; potassium hydroxide In water at 60℃; for 24 h; General procedure: The N-nucleophile (1.47 mmol), CuI (Sigma-Aldrich, 99.999percent purity, 0.147 mmol), MnF2 (Sigma-Aldrich, 98percent purity, 0.441 mmol), KOH (2.94 mmol), the aryl halide (2.21 mmol), trans-1,2-diaminocyclohexane (0.294 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 60C for 24 h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of known products was confirmed by 1H and 13C NMR spectroscopic analysis.

Reference: [1] Advanced Synthesis and Catalysis, 2007, vol. 349, # 17-18, p. 2673 - 2676
[2] Journal of Chemical Research, 2013, vol. 37, # 10, p. 636 - 637
[3] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6360 - 6363
[4] Chinese Chemical Letters, 2014, vol. 25, # 5, p. 775 - 778
[5] Advanced Synthesis and Catalysis, 2009, vol. 351, # 5, p. 720 - 724
[6] Advanced Synthesis and Catalysis, 2010, vol. 352, # 18, p. 3241 - 3245
[7] Angewandte Chemie - International Edition, 2007, vol. 46, # 46, p. 8862 - 8865
[8] Journal of Organic Chemistry, 2009, vol. 74, # 19, p. 7514 - 7517
[9] Chemistry - A European Journal, 2009, vol. 15, # 13, p. 3072 - 3075
[10] Tetrahedron Letters, 2011, vol. 52, # 52, p. 7171 - 7174
[11] Chemical Communications, 2009, # 41, p. 6258 - 6260
  • 2
  • [ 529-28-2 ]
  • [ 4897-68-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2008, vol. 47, # 27, p. 5063 - 5066
  • 3
  • [ 1663-39-4 ]
  • [ 529-28-2 ]
  • [ 443777-09-1 ]
  • [ 121-71-1 ]
  • [ 94113-07-2 ]
  • [ 474097-69-3 ]
Reference: [1] Organic Letters, 2003, vol. 5, # 13, p. 2231 - 2234
  • 4
  • [ 579-75-9 ]
  • [ 529-28-2 ]
  • [ 2786-00-7 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 33, p. 11527 - 11536
  • 5
  • [ 529-28-2 ]
  • [ 79-10-7 ]
  • [ 6099-03-2 ]
Reference: [1] Applied Organometallic Chemistry, 2012, vol. 26, # 1, p. 16 - 20
  • 6
  • [ 529-28-2 ]
  • [ 107-18-6 ]
  • [ 33538-83-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 6, p. 941 - 946
[2] Chemical Communications, 2016, vol. 52, # 17, p. 3532 - 3535
  • 7
  • [ 529-28-2 ]
  • [ 64-19-7 ]
  • [ 5399-03-1 ]
YieldReaction ConditionsOperation in experiment
56% at 0 - 50℃; for 1 h; Inert atmosphere 2-Iodo-l-methoxy-4-nitrobenzene (45). To a stirred solution of commercially available iodoanisole (1 mL, 7.7 mmol) in AcOH (2 mL) was added fuming nitric acid (0.8 mL, 17 mmol) dropwise at 0°C. The mixture was let to warm up to rt and then heated up to 50°C and stirred for lh under a N2 atmosphere when the color of the mixture became dark red/orange. Solid precipitate formed on cooling which was collected by filtration. Solid was washed with a 4:1 mixture of EtOH:H20 (10 mL) and dried on high vacuum to give 45 (1.2g, 56percent) as a light orange solid. ]H NMR (400 MHz, CDC13) δ 8.66 (s, 1H), 8.24 (d, J = 8.88 Hz, 1H), 6.85 (d, J = 8.88 Hz, 1H), 3.98 (s, 3H); 13C NMR (100 MHz, CDC13) δ 163.01, 141.88, 135.10, 125.69, 109.56, 85.13, 57.13; ESI MS: m/z 279.8 (M+H)+
Reference: [1] Patent: WO2013/52943, 2013, A2, . Location in patent: Page/Page column 110
  • 8
  • [ 529-28-2 ]
  • [ 5399-03-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4111 - 4133
[2] Chemische Berichte, 1896, vol. 29, p. 1000,2595[3] Bulletin de la Societe Chimique de France, 1896, vol. <3> 15, p. 641
[4] Chemische Berichte, 1896, vol. 29, p. 1000,2595[5] Bulletin de la Societe Chimique de France, 1896, vol. <3> 15, p. 641
[6] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 10, p. 2639 - 2646
  • 9
  • [ 529-28-2 ]
  • [ 7697-37-2 ]
  • [ 64-19-7 ]
  • [ 5399-03-1 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 1000,2595[2] Bulletin de la Societe Chimique de France, 1896, vol. <3> 15, p. 641
  • 10
  • [ 529-28-2 ]
  • [ 74-89-5 ]
  • [ 10541-78-3 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 4, p. 1180 - 1183
  • 11
  • [ 529-28-2 ]
  • [ 74587-12-5 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 13, p. 5000 - 5003
[2] Chemische Berichte, 1896, vol. 29, p. 1000,2595[3] Bulletin de la Societe Chimique de France, 1896, vol. <3> 15, p. 641
  • 12
  • [ 529-28-2 ]
  • [ 98273-59-7 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 1410
  • 13
  • [ 67-66-3 ]
  • [ 529-28-2 ]
  • [ 7726-95-6 ]
  • [ 98273-59-7 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 1410
  • 14
  • [ 529-28-2 ]
  • [ 28896-47-1 ]
  • [ 755027-21-5 ]
Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 21, p. 6233 - 6244
  • 15
  • [ 529-28-2 ]
  • [ 5397-34-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1942, vol. <2> 160, p. 41,63
  • 16
  • [ 110-00-9 ]
  • [ 529-28-2 ]
  • [ 38527-59-2 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 12, p. 2501 - 2504
  • 17
  • [ 529-28-2 ]
  • [ 667-27-6 ]
  • [ 1150164-80-9 ]
YieldReaction ConditionsOperation in experiment
96% With copper In dimethyl sulfoxide at 60℃; for 12 h; Inert atmosphere General procedure: To a suspension of activated Cu powder (2.6 eq.) in DMSO (0.38 M) was added the appropriate aryl iodide (1.0 eq.) and ethyl bromodifluoroacetate (1.0 eq.) or ethyl bromofluoroacetate (1.0 eq.) under nitrogen atmosphere. The reaction mixture was stirred at 60°C for 12 h. The reaction mixture was filtered through a pad of Celite® and washed with Et2O. The mixture was washed with aq. NH4Cl (sat., 2x) and brine (2x), then dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography.
Reference: [1] Synlett, 2016, vol. 27, # 1, p. 25 - 28
[2] Organic Letters, 2013, vol. 15, # 11, p. 2648 - 2651
[3] European Journal of Organic Chemistry, 2016, vol. 2016, # 33, p. 5529 - 5538
[4] European Journal of Organic Chemistry, 2017, vol. 2017, # 40, p. 6052 - 6059
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