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Chemical Structure| 619-58-9

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Product Details of 4-Iodobenzoic acid

CAS No. :619-58-9
Formula : C7H5IO2
M.W : 248.02
SMILES Code : O=C(O)C1=CC=C(I)C=C1
MDL No. :MFCD00002533
InChI Key :GHICCUXQJBDNRN-UHFFFAOYSA-N
Pubchem ID :12085

Safety of 4-Iodobenzoic acid

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

Application In Synthesis of 4-Iodobenzoic acid

* 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 [ 619-58-9 ]

[ 619-58-9 ] Synthesis Path-Downstream   1~19

  • 2
  • [ 94-26-8 ]
  • [ 619-58-9 ]
  • 4-(n-Butoxycarbonyl)phenyl 4'-iodobenzoate [ No CAS ]
  • 3
  • [ 619-58-9 ]
  • [ 10602-00-3 ]
  • [ 16819-43-5 ]
  • [ 116075-75-3 ]
  • 4
  • [ 619-58-9 ]
  • [ 7697-37-2 ]
  • [ 35674-27-2 ]
  • 5
  • [ 20651-67-6 ]
  • [ 64-19-7 ]
  • chromium trioxide [ No CAS ]
  • [ 619-58-9 ]
  • 6
  • [ 619-58-9 ]
  • [ 1692-15-5 ]
  • [ 4385-76-6 ]
  • 7
  • [ 619-58-9 ]
  • [ 5720-07-0 ]
  • [ 725-14-4 ]
YieldReaction ConditionsOperation in experiment
95% With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃; for 6h;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) and evaporated under reduced pressure to yield a combined 1.5O g (95%). 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 1h; 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 %) 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.
  • 8
  • [ 67-56-1 ]
  • [ 619-58-9 ]
  • [ 14047-29-1 ]
  • [ 792-74-5 ]
  • 9
  • [ 158937-25-8 ]
  • [ 619-58-9 ]
  • [ 158938-08-0 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 18h;Heating / reflux; 25 g (0,088 mol) 4'-n-Pentoxy[1,1']biphenyl-4-boronsaeure und 21,8 g (0,088 mol) 4-lodbenzoesaeure werden unter Inertgasatmosphaere in einer Mischung aus 270 ml Ethanol, 750 ml Toluol und 132 ml einer 2M Sodaloesung suspendiert, mit 5,08 g (4,4 mmol) Tetrakis(triphenylphosphin)palladium versetzt und im Anschluss daran 18 Stunden unter Rueckfluss erhitzt. Die grau-braune Mischung wird abgekuehlt, angesaeuert und mit Ethylacetat extrahiert. Die organische Phase wird mit Wasser und gesaettigter Kochsalzloesung gewaschen, getrocknet (Natriumsulfat) und ueber Celite filtriert. Nach Entfernen der Loesungsmittel erhaelt man 1,2 g eines Feststoffes, der nach HPLC-Analyse (Vergleich mit Referenzsubstanz) jedoch keinerlei 4"-n-Pentoxy[1,1':4',1"]terphenyl-4-carbonsaeure enthaelt. Eine Bildung von 4-n-Pentoxy[1,1':4',1"]terphenyl-4-carbonsaeure hat auf dem in WO 94/25050 angegebenen Syntheseweg offensichtlich nicht stattgefunden.
  • 10
  • [ 619-58-9 ]
  • [ 175883-62-2 ]
  • [ 71-36-3 ]
  • [ 885965-61-7 ]
YieldReaction ConditionsOperation in experiment
30% With caesium carbonate;tetrakis(triphenylphosphine)palladium (0); In water; ethyl acetate; toluene; Step 1: 3-Methyl-4-methoxyphenylboronic acid (542 mg) was combined with 4-iodobenzoic acid (810 mg), cesium carbonate (5.32 g), toluene (16 mL), water (8 mL) and n-butanol (4 mL). The mixture was degassed under vacuum with argon purging after which, tetrakis-triphenylphosphine palladium (38 mg) was added. The reaction was heated to 80 C. for 20 hours after which, it was cooled to room temperature and diluted with ethyl acetate (16 mL). The layers were separated and the organics were concentrated to dryness. The residue was purified on silica gel (50% to 100% ethyl acetate/hexane over 40 minutes) giving 3'-methyl-4'-methoxy-4-biphenylcarboxylic acid (240 mg). Yield=30%
  • 11
  • [ 619-58-9 ]
  • [ 126617-98-9 ]
  • 2'-methoxymethyl-biphenyl-4-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); at 90℃; for 19h; Example 61 10-[2'-(METHOXYMETHYL)-1,1'-BIPHENYL-4-YL]CARBONYL}-N-(PYRIDIN-3-YLMETHYL)-10,11-DIHYDRO-5H-PYRROLO[2,1-C][1,4]BENZODIAZEPINE-3-CARBOXAMIDE Step A. 2'-Methoxymethyl-biphenyl-4-carboxylic acid; To a suspension of 4-iodobenzoic acid (0.82 g, 3.31 mmol) and <strong>[126617-98-9]2-methoxymethylphenylboronic acid</strong> (0.55 g, 3.31 mmol) in dry acetonitrile (30 mL) was added a 0.4 M aqueous sodium carbonate solution (30 mL) and the reaction mixture purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (90 mg, 0.078 mmol) was then added and the reaction mixture heated to 90 C. for 19 hours. The hot reaction mixture was filtered through celite, concentrated in vacuo to remove acetonitrile and the resulting aqueous suspension washed with ethyl acetate (2×30 mL). The aqueous phase was acidified to pH 1 by the addition of concentrated hydrochloric acid, the resulting white suspension cooled to 4 C. for 1 hour and the solid product filtered. Recrystallization from dichloroethane gave the title compound (0.469 g, 59%) as a white solid, m.p. 164.5-165.5 C. MS [(-)ESI, m/z]: 241 [M-H]-
  • 12
  • [ 619-58-9 ]
  • [ 39987-25-2 ]
  • [ 876587-82-5 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 45℃; Iminodiacetic dimethyl ester hydrochloride (624 mg, 3.24 mmol) was suspended in 5 mL of anhydrous DMF under nitrogen, and N-methylmorpholine (360 muL, 3.27 mmol) was added. After 5 minutes, 4-iodobenzoic acid (805 mg, 3.25 mmol) was added, followed by HOBt (450 mg, 3.33 mmol) and EDC (1.0 g, 5.28 mmol). The reaction was stirred overnight at 45 0C. The solvent was removed and the residue was dissolved in EtOAc (20 mL) and washed with 0.5 M HCl, sat. NaHCO3 and water. The organic phase was collected, the solvent removed and the mixture purified by column chromatography (silica; hexanes : EtOAc 90:10 - 65:45), yielding the product as a white solid. MS(ES+): Cal'd. 392.00 (MH+), exp. 391.98 (MH+).
  • 13
  • [ 619-58-9 ]
  • [ 163520-14-7 ]
  • [ 1059103-86-4 ]
  • 15
  • [ 619-58-9 ]
  • potassium 4-(methoxy)phenyltrifluoroborate [ No CAS ]
  • [ 725-14-4 ]
  • 16
  • [ 619-58-9 ]
  • [ 97963-62-7 ]
  • 4-[5-(difluoromethoxy)-1H-benzimidazol-2-yl]sulfanyl}benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 22h; General procedure: CuI (0.05 equiv), 1,10-phenanthroline (0.1 equiv) and K2CO3 (2 equiv) were placed in an oven-dried screw-capped test tube with Teflon-lined septum that was filled with nitrogen. About 2.5 mL of dry DMF was then added at room temperature. Now the corresponding aryl iodide (1.0 mmol) was added followed by MBI or FMBI (1.0 equiv) and the tube was placed in the preheated oil bath at 140 C and the reaction mixture was magnetically stirred for 22 h. After complete disappearance of iodobenzene (the progress of the reaction was followed by TLC), the reaction mixture was allowed to cool to room temperature. Then water was added and the reaction mixture was extracted with ethyl acetate. After removal of the solvent in vacuum, the crude residue was purified by column chromatography.5- (or 6-) (Difluoromethoxy)-2-(phenylsulfanyl)-1H-benzimidazole (1).
  • 18
  • [ 619-58-9 ]
  • [ 216019-28-2 ]
  • 3'‐iso-propyl‐(1,1'‐biphenyl)‐4‐carboxylic acid [ No CAS ]
  • 19
  • [ 619-58-9 ]
  • [ 116075-75-3 ]
 

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