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Product Details of [ 619-58-9 ]

CAS No. :619-58-9 MDL No. :MFCD00002533
Formula : C7H5IO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GHICCUXQJBDNRN-UHFFFAOYSA-N
M.W :248.02 Pubchem ID :12085
Synonyms :

Calculated chemistry of [ 619-58-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.12
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.52
Log Po/w (XLOGP3) : 3.02
Log Po/w (WLOGP) : 1.99
Log Po/w (MLOGP) : 2.52
Log Po/w (SILICOS-IT) : 2.18
Consensus Log Po/w : 2.25

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.66
Solubility : 0.0545 mg/ml ; 0.00022 mol/l
Class : Soluble
Log S (Ali) : -3.47
Solubility : 0.0844 mg/ml ; 0.00034 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.73
Solubility : 0.465 mg/ml ; 0.00187 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.57

Safety of [ 619-58-9 ]

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 [ 619-58-9 ]

* 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.

  • Upstream synthesis route of [ 619-58-9 ]
  • Downstream synthetic route of [ 619-58-9 ]

[ 619-58-9 ] Synthesis Path-Upstream   1~42

  • 1
  • [ 619-58-9 ]
  • [ 1692-15-5 ]
  • [ 4385-76-6 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 27, p. 5095 - 5098
  • 2
  • [ 186581-53-3 ]
  • [ 619-58-9 ]
  • [ 31827-94-8 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 13, p. 5191 - 5193
  • 3
  • [ 64-18-6 ]
  • [ 591-50-4 ]
  • [ 619-58-9 ]
  • [ 88-67-5 ]
  • [ 618-51-9 ]
Reference: [1] Organic Letters, 2004, vol. 6, # 14, p. 2437 - 2439
  • 4
  • [ 619-58-9 ]
  • [ 5713-61-1 ]
  • [ 29886-62-2 ]
Reference: [1] Journal of Organometallic Chemistry, 1990, vol. 390, # 3, p. 389 - 398
  • 5
  • [ 6165-68-0 ]
  • [ 619-58-9 ]
  • [ 29886-62-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 24, p. 10994 - 11005
[2] Journal of Organic Chemistry, 1996, vol. 61, # 15, p. 5169 - 5171
  • 6
  • [ 619-58-9 ]
  • [ 54663-78-4 ]
  • [ 29886-62-2 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 24, p. 4175 - 4178
  • 7
  • [ 619-58-9 ]
  • [ 35674-27-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 9, p. 1896 - 1904
[2] Dalton Transactions, 2015, vol. 44, # 5, p. 2047 - 2051
[3] Chemical Communications, 2017, vol. 53, # 55, p. 7808 - 7811
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 1865 - 1877
[5] Chemische Berichte, 1875, vol. 8, p. 562
  • 8
  • [ 619-58-9 ]
  • [ 7697-37-2 ]
  • [ 35674-27-2 ]
Reference: [1] Chemische Berichte, 1875, vol. 8, p. 562
  • 9
  • [ 619-58-9 ]
  • [ 71441-28-6 ]
Reference: [1] Patent: US8293803, 2012, B2,
  • 10
  • [ 619-58-9 ]
  • [ 402-43-7 ]
  • [ 1891-90-3 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 7, p. 1197 - 1200
  • 11
  • [ 619-58-9 ]
  • [ 214360-73-3 ]
  • [ 5730-78-9 ]
Reference: [1] Patent: US2003/153556, 2003, A1,
  • 12
  • [ 619-58-9 ]
  • [ 10602-00-3 ]
  • [ 16819-43-5 ]
  • [ 116075-75-3 ]
Reference: [1] Tetrahedron, 1995, vol. 51, # 8, p. 2325 - 2330
  • 13
  • [ 64-17-5 ]
  • [ 619-58-9 ]
  • [ 51934-41-9 ]
YieldReaction ConditionsOperation in experiment
96.1% With hydrogenchloride In water for 2 h; Reflux Synthesis of ethyl 4-iodobenzoate
A mixture of 4-iodobenzoic acid, 25 ml ethyl alcohol and 20 ml solution of dry HCl in ethyl alcohol was refluxed for 2 hours.
The solid was dissolved after 1 hour of boiling.
The reaction solution was cooled to room temperature and evaporated under vacuum to a volume of 10 ml.
A lower organic layer formed with the chemical conversion of the acid to the ester.
The resulting mixture was cooled in an ice bath.
To this mixture 80 ml of diethyl ether, dry sodium hydrogen carbonate (I gram) and 50 grams of ice were added.
This solution was stirred, washed by dissolution of a saturated solution of sodium bicarbonate in 50 ml water and water, dried over sodium sulfate, and evaporated under vacuum, yielding ethyl 4-iodobenzoate as a liquid oil product (5.43 gram, 96.1percent yield) [1H-NMR (CDCl3): d7.8 (s, 1H), d7.79 (s, 1H), 7.6 (s, 1H), d4.4 (d, 2H, J=7.1 Hz), d1.4 (s, 3H)].
95.5% for 5.5 h; Reflux In a 250 mL three-necked flask,Iodobenzoic acid (20.0 g, 80.6 mmol) was dissolved in ethanol (100.0 mL)98percent concentrated sulfuric acid (8.7 g, 88.7 mmol) was slowly added,The reaction was refluxed for 5.5 h.The reaction is completed,The mixture was evaporated to dryness under reduced pressure and the residue was washed with water (20 mL × 2)Vacuum dried to give 4-iodobenzoate 21.3g,Yield 95.5percent.
85% at 100℃; for 24 h; General procedure: A mixture of acid (0.2 mmol), alcohol (0.6 mmol) and GO (50 wtpercent, calculated with the mass of acid) in ethyl alcohol or DCE (1 mL) was placed in a test tube equipped with a magnetic stirring bar. The mixture was stirred at 100 °C for 24 h. After the reaction was finished, filtered the GO, solvent was removed, and the residue was separated by column chromatography to give the pure sample.
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 10, p. 2278 - 2288
[2] Patent: US2016/97037, 2016, A1, . Location in patent: Paragraph 0438
[3] Dalton Transactions, 2015, vol. 44, # 19, p. 9269 - 9280
[4] Patent: CN106565761, 2017, A, . Location in patent: Paragraph 0029; 0030; 0053; 0054; 0069; 0070
[5] Synthesis, 2008, # 4, p. 605 - 609
[6] Synlett, 2017, vol. 28, # 8, p. 981 - 985
[7] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 11, p. 2663 - 2673
[8] Monatshefte fuer Chemie, 1946, vol. 76, p. 29
[9] Justus Liebigs Annalen der Chemie, 1881, vol. 207, p. 327
[10] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 12, p. 5044 - 5047
[11] Journal of Medicinal Chemistry, 2004, vol. 47, # 24, p. 5937 - 5944
[12] Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 9, p. 2079 - 2087
[13] Patent: US6344463, 2002, B1, . Location in patent: Page column 18
[14] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 6014 - 6024
[15] Transition Metal Chemistry, 2015, vol. 40, # 6, p. 665 - 671
[16] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 355 - 360
[17] RSC Advances, 2018, vol. 8, # 12, p. 6306 - 6314
  • 14
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  • [ 51934-41-9 ]
Reference: [1] Patent: US5877207, 1999, A,
[2] Patent: US5958954, 1999, A,
[3] Patent: US5919970, 1999, A,
[4] Patent: US6025388, 2000, A,
[5] Patent: US6037488, 2000, A,
[6] Patent: US5202471, 1993, A,
[7] Patent: US5489584, 1996, A,
[8] Patent: US5534641, 1996, A,
[9] Patent: US5616712, 1997, A,
[10] Patent: US5399561, 1995, A,
[11] Patent: US5688957, 1997, A,
[12] Patent: US4980369, 1990, A,
[13] Patent: US4739098, 1988, A,
[14] Patent: US4810804, 1989, A,
[15] Patent: EP290130, 1991, B1,
[16] Patent: US2004/102360, 2004, A1,
[17] Patent: US3957871, 1976, A,
  • 15
  • [ 619-58-9 ]
  • [ 485817-30-9 ]
  • [ 51934-41-9 ]
Reference: [1] Organometallics, 2016, vol. 35, # 19, p. 3406 - 3412
  • 16
  • [ 619-58-9 ]
  • [ 485817-30-9 ]
  • [ 51934-41-9 ]
Reference: [1] Organometallics, 2016, vol. 35, # 19, p. 3406 - 3412
  • 17
  • [ 619-58-9 ]
  • [ 75-03-6 ]
  • [ 51934-41-9 ]
Reference: [1] European Journal of Organic Chemistry, 2013, # 26, p. 5886 - 5892
  • 18
  • [ 619-58-9 ]
  • [ 16004-15-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 9, p. 3187 - 3200
  • 19
  • [ 619-58-9 ]
  • [ 10602-00-3 ]
Reference: [1] Chemical Communications, 2006, # 13, p. 1430 - 1432
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9562 - 9575
  • 20
  • [ 619-58-9 ]
  • [ 5720-07-0 ]
  • [ 725-14-4 ]
YieldReaction ConditionsOperation in experiment
95% With caesium carbonate In 1,2-dimethoxyethane; water at 80℃; for 6 h; Inert atmosphere Method B.A solution of 4-methoxyphenyl boronic acid (1 g, 6.58 mmol), 4-iodobenzoic acid (1.63 g, 6.58 mmol) and cesium carbonate (5.36 g, 16.45 mmol) in 3:1 1,2- dimethoxyethane/water was deoxygenated with nitrogen for 15 minutes. Pd(PPtLs)4 (380 mg, 0.329 mmol) was then added and the solution was heated to 80° C for 6h. The reaction was allowed to cool and acidified with 2M HCl which caused a precipitate to form. The precipitate was filtered and the filtrate was extracted twice with dichloromethane. The organic layer was then dried over magnesium sulfate, filtered through diatomaceous earth filter aid (CELITE.(R).) and evaporated under reduced pressure to yield a combined 1.5O g (95percent). 1HNMR (DMSO): δ 7.99 (d, J=8.4 Hz, 2H), 7.74 (d, J=8.4 Hz, 2H), 7.69 (d, J=8.7 Hz, 2H), 7.04 (d, J=8.7 Hz, 2H), 3.80 (s, 3H). 13CNMR (DMSO): δ 167.17, 159.49, 143.90, 131.16, 129.91, 128.77, 128.09, 126.08, 114.45, 55.17.
89% With Pd/C; potassium carbonate In water at 110℃; for 1 h; General procedure: The Ni and Pd carbon aerogels were always sinked in water 24 h before their use as catalysts and kept in the same solvent.Catalytic reactions: In a 100 mL three necked round-bottom flask, arylboronic acid (15 mmol), aryl halide (10 mmol) and K2CO3 (2.76 g, 20 mmol) were dissolved in 20 mL of H2O. Then, Ni or Pd carbon aerogel (0.1 mmol, 1 mol percent) was added to the mixture and the reaction was carried out under reflux (110 °C), in the presence of air and mechanical stirring. Periodic sampling of the reaction media was made to analyze the reaction evolution by GC and 1H NMR measurements. The liquid phase was decanted and the carbon aerogel was washed with water. This water extracts and the reactive solution were mixed together and acidified until pH 1 to cause the precipitation of the final product. The solid was filtrated, washed with water and dried. The pieces of aerogel were washed with AcOEt, with water and were kept submerged in this solvent before reused.
Reference: [1] Russian Chemical Bulletin, 2007, vol. 56, # 2, p. 369 - 370
[2] Green Chemistry, 2010, vol. 12, # 1, p. 150 - 158
[3] Patent: WO2009/146013, 2009, A1, . Location in patent: Page/Page column 52
[4] Green Chemistry, 2009, vol. 11, # 12, p. 1929 - 1932
[5] Tetrahedron, 2012, vol. 68, # 32, p. 6517 - 6520
[6] Green Chemistry, 2013, vol. 15, # 12, p. 3468 - 3473
[7] Tetrahedron Letters, 2006, vol. 47, # 25, p. 4225 - 4229
  • 21
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  • [ 725-14-4 ]
Reference: [1] Green Chemistry, 2010, vol. 12, # 1, p. 150 - 158
  • 22
  • [ 619-58-9 ]
  • [ 79-10-7 ]
  • [ 19675-63-9 ]
YieldReaction ConditionsOperation in experiment
73% With tributyl-amine; potassium carbonate In N,N-dimethyl-formamideGreen chemistry General procedure: In a typical reaction, aryl halides (9 mmol), phenylethylene (15 mmol) (or acrylic acid), tributylamine (30 mmol) and DMF (10 mL) were placed in a round-bottomed flask with 1.47 molpercent AOFs–Ni(0) as catalyst. The reaction was carried out in a temperature controlled oil bath. After completion of the reaction, the mixture was cooled to room temperature. Then the AOFs–Ni(0) was separated from the mixture by filtration and washed sequentially with hot ethanol and reused in thenext reaction. The filtrate was extracted with ethyl acetate (30 mL) and washed with distilled water (3 × 15 mL). The solvent was then removed by rotary evaporation to give a crude product. The crude product was purified by column chromatography on H 60-silica powder using mixed solvent (petroleum ether/ethyl acetate = 3/1). The pure products were characterised by melting point, 1H NMR, HRMS and GC-MS spectroscopy.#10;#10;
Reference: [1] RSC Advances, 2016, vol. 6, # 20, p. 16115 - 16121
[2] Applied Organometallic Chemistry, 2012, vol. 26, # 1, p. 16 - 20
[3] Journal of Chemical Research, 2016, vol. 40, # 3, p. 164 - 166
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  • [ 89976-27-2 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 5, p. 427 - 432
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 1865 - 1877
[3] Dalton Transactions, 2015, vol. 44, # 5, p. 2047 - 2051
[4] Patent: US2016/333004, 2016, A1,
[5] Chemical Communications, 2017, vol. 53, # 55, p. 7808 - 7811
  • 24
  • [ 619-58-9 ]
  • [ 39959-59-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 9, p. 3187 - 3200
  • 25
  • [ 619-58-9 ]
  • [ 4334-88-7 ]
Reference: [1] Patent: CN106565761, 2017, A,
[2] Patent: CN106565761, 2017, A,
  • 26
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  • [ 249647-25-4 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 47, p. 15467 - 15472
  • 27
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  • [ 865-47-4 ]
  • [ 120363-13-5 ]
YieldReaction ConditionsOperation in experiment
99.9%
Stage #1: at 75℃; for 1 h; Inert atmosphere
Stage #2: at 0℃; for 0.5 h;
Thionyl chloride (2.30 ml, 32.30 mmol) and N,N-dimethylformamide (DMF) (0.02 ml, 0.20 mmol) were added to 4-iodobenzoic acid (1.00 g, 4.00 mmol), and then the reaction system was substituted with nitrogen, heated to 75 °C, refluxed, and then stirred for 1 hour. The reaction solution was concentrated under reduced pressure, the obtained residue was dissolved in tetrahydrofuran (5 ml), and then a potassium tert-butoxide 1M solution in THF (4.5 ml) was slowly added at a sub-zero temperature, and stirred for 30 minutes. The reaction solution was concentrated under reduced pressure, and the obtained residue was diluted with ethyl acetate and washed with water and brine. An organic solvent layer was collected, dehydrated with anhydrous magnesium sulfate (MgSO4), filtered, and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (Hex:EA=9:1), thereby obtaining 2-(trimethylsilyl)ethyl 4-iodobenzoate (14.00 g, 99.9percent yield). 1H NMR (CDCl3, 400 MHz) δ 7.77 (2H, d, J = 7.5 Hz, aromatic), 7.69 (2H, d, J = 8.0 Hz, aromatic), 1.59 (9H, s, (CH3)3).
Reference: [1] Patent: EP3327000, 2018, A1, . Location in patent: Paragraph 0116
[2] Bioconjugate Chemistry, 2015, vol. 26, # 2, p. 197 - 200
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  • [ 115-11-7 ]
  • [ 120363-13-5 ]
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 24, p. 7947 - 7952
[2] Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 7952 - 7966
[3] Patent: US2001/44535, 2001, A1,
  • 29
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  • [ 36805-97-7 ]
  • [ 120363-13-5 ]
Reference: [1] Patent: WO2007/128817, 2007, A2, . Location in patent: Page/Page column 90
  • 30
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  • [ 75-65-0 ]
  • [ 120363-13-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 415 - 420
  • 31
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  • [ 120363-13-5 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 10, p. 3585 - 3591
[2] Patent: JP2015/848, 2015, A,
  • 32
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  • [ 111291-97-5 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 10, p. 3585 - 3591
  • 33
  • [ 619-58-9 ]
  • [ 100-39-0 ]
  • [ 136618-42-3 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide for 0.166667 h;
Stage #2: at 20℃; for 6.25 h;
To 4-iodobenzoic acid (15.62g, 63mmol, 1.05eq) in dry DMF (6vol, 90ml) was added potassium carbonate (8.7g, 63mmol, 1.05eq) and the suspension was stirred for 10min. Benzyl bromide (10.25g, 7.13ml, 60mmol, 1 eq) was then added over ca. 1 min. and the resulting suspension was stirred at room temperature under nitrogen for 6.25hr. The mixture was partitioned between ether (200ml) and water (200ml). The aqueous phase was extracted with more ether, then the combined organics were washed with water, aqueous lithium chloride, brine, dried and then evaporated to give the title compound as a white crystalline solid after leaving under vacuum (18.38g, 86percent). LCMS; tRET = 3.81 min, 70percent ES +ve 376, 356 (+ artefact 1.48min. 28percent). <n="61"/>1H NMR (400 MHz, DMSOd6) δppm 7.92 (d, 2H) 7.74 (d, 2H) 7.46 (d, 2H) 7.35 - 7.42 (m, 3H) 5.34 (s, 2H).
Reference: [1] Patent: WO2009/74590, 2009, A1, . Location in patent: Page/Page column 59-60
[2] Patent: WO2009/50220, 2009, A1, . Location in patent: Page/Page column 42
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  • [ 7285-83-8 ]
  • [ 136618-42-3 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 36, p. 7997 - 8002
  • 35
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  • [ 100-51-6 ]
  • [ 136618-42-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 18, p. 2443 - 2446
  • 36
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  • [ 158938-08-0 ]
Reference: [1] Patent: EP1156997, 2004, B1, . Location in patent: Page 3; 12
  • 37
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  • [ 89878-14-8 ]
  • [ 4385-75-5 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 15, p. 5169 - 5171
  • 38
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  • [ 25015-63-8 ]
  • [ 180516-87-4 ]
Reference: [1] Patent: US6680401, 2004, B1, . Location in patent: Page column 21
  • 39
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  • [ 180516-87-4 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
  • 40
  • [ 619-58-9 ]
  • [ 128796-39-4 ]
  • [ 195457-71-7 ]
YieldReaction ConditionsOperation in experiment
86% With Pd/C; potassium carbonate In water at 110℃; for 48 h; General procedure: The Ni and Pd carbon aerogels were always sinked in water 24 h before their use as catalysts and kept in the same solvent.Catalytic reactions: In a 100 mL three necked round-bottom flask, arylboronic acid (15 mmol), aryl halide (10 mmol) and K2CO3 (2.76 g, 20 mmol) were dissolved in 20 mL of H2O. Then, Ni or Pd carbon aerogel (0.1 mmol, 1 mol percent) was added to the mixture and the reaction was carried out under reflux (110 °C), in the presence of air and mechanical stirring. Periodic sampling of the reaction media was made to analyze the reaction evolution by GC and 1H NMR measurements. The liquid phase was decanted and the carbon aerogel was washed with water. This water extracts and the reactive solution were mixed together and acidified until pH 1 to cause the precipitation of the final product. The solid was filtrated, washed with water and dried. The pieces of aerogel were washed with AcOEt, with water and were kept submerged in this solvent before reused.
Reference: [1] Green Chemistry, 2010, vol. 12, # 1, p. 150 - 158
[2] Tetrahedron, 2012, vol. 68, # 32, p. 6517 - 6520
[3] Patent: WO2004/81005, 2004, A1, . Location in patent: Page 135-136
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  • [ 1423-26-3 ]
  • [ 195457-70-6 ]
Reference: [1] Patent: US2006/183754, 2006, A1, . Location in patent: Page/Page column 25
  • 42
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  • [ 99768-12-4 ]
Reference: [1] Patent: CN106565761, 2017, A,
[2] Patent: CN106565761, 2017, A,
[3] Patent: CN106565761, 2017, A,
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