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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: 2-Iodobenzoic acid
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Batch number can be found on the product's label following the word 'Batch'.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 88-67-5 |
Formula : | C7H5IO2 |
M.W : | 248.02 |
SMILES Code : | O=C(O)C1=CC=CC=C1I |
Synonyms : |
2-Iodobenzoic acid
|
MDL No. : | MFCD00002419 |
InChI Key : | CJNZAXGUTKBIHP-UHFFFAOYSA-N |
Pubchem ID : | 6941 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With sulfuric acid; nitric acid; at 135℃; for 1h; | During this preparation up to 25 mmol I2 are formed. Therefore, the synthesis has to be conducted in a well-ventilated fume cupboard. Prepared according to literature procedure [10]. 2-Iodobenzoic acid (4, 10 g, 40.3 mmol, 1 equiv) was added to a mixture of HNO3 (35 mL, 65%) and H2SO4 (85 mL, 95%). The solution was heated to 135 C and stirred for 1 h. Subsequently, the resulting brown slurry was poured onto ice and the grey precipitate was filtered off and washed with copious amounts of water. Then, the filtrate was suspended in water (100 mL), heated to 100 C and treated with a solution of KI (8.5 g, 51.2 mmol, 1.3 equiv) and H2SO4 (5 drops) in water (10 mL) over the course of 1 h. Finally, the brown suspension was filtered hot and washed with water to afford the pure product (5 g, 42%) as a brown solid. If impure product is obtained, boiling with water followed by hot filtration can be applied. |
With nitric acid; In sulfuric acid; | EXAMPLE 1 2-Iodo-5-Nitrobenzoic Acid 2-Iodobenzoic acid (100 g) was dissolved in 400 mL of concentrated sulphuric acid and placed in a 2 liter 3 necked flask. The flask was fitted with reflux condenser, a thermometer and an addition funnel. Fuming nitric acid (400 ml) was added drop by drop. The addition was adjusted in such a way that the temperature was allowed to raise to 80 C. over a period of 2 hours. During the addition, the reaction mixture was stirred vigorously and maintained the temperature at 80 C. for an additional 2 hours. After the completion of the reaction, the reaction mixture was poured slowly into crushed ice (3 Kg). The contents were allowed to settle and were filtered. The yellow precipitate was collected and dried at 30 C. The yield was 90 grams. | |
With sulfuric acid; nitric acid; at 0 - 130℃; for 1.75h; | Prepared according to literature procedure. The 2-iodobenzoic acid (1,000 mg, 4.03 mmol) was pre-cooled at 0 C and then a solution of Conc. HNO3 (1.50 mL) and Conc. H2SO4 (4.50 mL) was added slowly. The mixture was allowed to stir at 0 C for 15 minutes, ice bath was moved, stirred at room temperature for 30 minutes, and followed by to stir the mixture at 130 C for 1 hour. The mixture was yellow, cooled with ice bath, then filtered with suction flask and Buchner funnel. The light yellow solid was obtain. 1H NMR (300 MHz, CDCl3) delta 8.12 (d, J = 2.3 Hz, 1H), 7.90 (d, J = 8.4 Hz, 1H), 7.33 (dd, J = 8.4, 2.3 Hz, 1H). Other data was identical to the literature values. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With copper (I) iodide; copper atom; potassium carbonate; In N,N-dimethyl-formamide; for 2.0h;Inert atmosphere; | To a solution of 7 (1.00 g, 4.03 mmol) in DMF (15 mL) was added K2CO3 (1.11 g, 8.08 mmol), CuI (38 mg, 0.02 mmol), Cu (26 mg, 0.04 mmol) and 8a (974 mg, 0.61 mmol). The resulting solution was heated to 130 C under N2 for 2 h. After filtration through celite, the filtrate was diluted with EtOAc (150mL × 1) and washed with distd H2O (450 mL × 5). The organic layer was dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was purified by silica gel chromatography (MeOH: CH2Cl2 = 0:100 - 2: 98) to give 9a (766 mg, 83%) as a solid. Mp 186-189 C. IR (KBr) 3335, 3052, 2868, 1652, 1578, 1509, 1258, 763 cm-1. 1H NMR (300 MHz, DMSO-d6) δ 13.04 (s, 1H), 9.53 (s, 1H), 7.89 (dd, J = 1.7, 7.9 Hz, 1H), 7.37 (td, J = 1.7, 7.8 Hz, 1H), 7.28 (m, 2H), 7.19 (m, 2H), 7.06 (dd, J = 0.9, 8.6 Hz, 1H), 6.76 (td, J = 0.9, 7.8 Hz, 1H). ESI-MS m/z: 230.1 (M-H)-. |
With copper atom; potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 20.0h;Schlenk technique; Inert atmosphere; | General procedure: A mixture of K2CO3 (1.0mmol, 1.0 eq), amine (1.2mmol, 1.2 eq), ortho-iodo benzoic acid (1.0mmol, 1.0 eq) and DMF (2.0mL) and copper powder (0.001mmol, 0.1% eq) were stirred in the schlenk tube for 12h at 100C under argon condition, and stopped heat and cooled to 25C. The solid (bottle green) was diluted with water, acidified with 2.0N HCl until pH 2 was adjusted. The black solid was precipitated and filtered. The filter cake was washed with an excess of water to remove the excess amine, dissolved in dichloromethane. The dichloromethan was concentrated by rotary evaporation under reduced pressure and dried over Na2SO4. The crude compounds, o-aminobenzoic acid derivatives, were obtained. Then o-aminobenzoic acid derivatives (1.0 eq), tryptamine (1.0 eq), EDCI·HCl (1.2 eq), HOBT (1.1 eq) were dissolved in dichloromethane (3mL), and Et3N (2.5 eq) was added at room temperature and stirred for 8h. After completion of the reaction detected by TLC, the reaction liquid was concentrated by rotary evaporation under reduced pressure. Then the resulting residue was purified by silica gel flash column chromatography to afford the desired product as a solid and the total yield was 49-95%. | |
With copper atom; potassium carbonate; In N,N-dimethyl-formamide;Heating; Inert atmosphere; | General procedure: A mixture of 2-iodobenzoic acid 1 (1.0 mmol), anilines(1 mmol) 2, K2CO3 (2.0 mmol), and Cu powder (0.1 mmol) in DMF(3 mL) were added in a pressure vessel and stirred at 110 C for 12 hunder nitrogen. Then added 30 mL water to the cooled reactionmixture and filtrated through Celite. The filtrate was acidified withHCl (2 M), and precipitation can be observed. Then the insoluble crude product is obtained by filtration and purified by rinsing with5% aqueous Na2CO3 to afford the product 3 |
With copper atom; potassium carbonate; In N,N-dimethyl-formamide;Heating; Inert atmosphere; | General procedure: A mixture of 2-iodobenzoic acid 1 (1.0 mmol), anilines(1 mmol) 2, K2CO3 (2.0 mmol), and Cu powder (0.1 mmol) in DMF(3 mL) were added in a pressure vessel and stirred at 110 C for 12 hunder nitrogen. Then added 30 mL water to the cooled reactionmixture and filtrated through Celite. The filtrate was acidified withHCl (2 M), and precipitation can be observed. Then the insoluble crude product is obtained by filtration and purified by rinsing with5% aqueous Na2CO3 to afford the product 3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.6 g (69.4%) | With potassium carbonate; | EXAMPLE 11 5-Amino-2-methyl-6H-pyrazolo[4,5,1-d,e]acridin-6-one (Compound 11): 3-Methyl-6-nitroindazole (64.5 g), 46.0 g of 2-iodobenzoic acid, 40.8 g of potassium carbonate and 1.89 g of copper(II) oxide were subjected to reaction in the same manner as in Example 1 to obtain 53.6 g (69.4percent) of 1-(2-carboxyphenyl)-<strong>[6494-19-5]3-methyl-6-nitroindazole</strong>. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With copper(l) iodide; TPGS-450-M; caesium carbonate; In water; at 20℃; for 12h;Inert atmosphere; Green chemistry; | General procedure: A two-neck round bottom flask was charged with a magnetic stirrer, evacuated and backfilled with nitrogen. Substituted 2-halobenzoic acid (1, 0.5 mmol) and amidine hydrochloride (2, 0.75 mmol) or bis(guanidine) sulphate (2, 0.38 mmol) in 2 wt percent TPGS-750-M (3 mL) were added under nitrogen atmosphere. After a 10-min stirring, Cs2CO3 (1 mmol, 326 mg) was added to the flask. 15 min later, CuI (0.1 mmol, 19 mg) was added to the flask. The mixture was allowed to stir under nitrogen atmosphere at the shown temperature for 12 h (see Table 3 in text). After completion of the reaction, the mixture was extracted with EtOAc (1 mL), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (3:1 to 1:1) as eluent to provide the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 24h; | 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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Synthesized according to a slight modification of two previously reported procedures.18 Neat2-iodobenzoic acid (3.00 g, 12.1 mmol) was cooled down to 0 C, to which was added a mixture offuming HNO3 (3.0 mL) and concentrated H2SO4 (13.5 mL). This mixture was then stirred at 0 C for 1 h,then at rt for 30 min, and finally at 135 C for 2 h, before being cooled back down to rt. The resultingsolution was poured into plenty of ice water and filtered. The solid was transferred to an Erlenmeyer flaskand suspended in water (300 mL), then heated to a boil. A solution of KI (2.41 g, 14.5 mmol) in water (15mL) acidified to pH 3 with a few drops of concentrated H2SO4 was added portion-wise to this boiling suspension (I2 vapors were generated with each portion). Omitting this step as in Subramanian?s reportyields the iodoso analog. The solution was filtered while still boiling, then the filtrate was stored at 4 Cfor 18 h after which time the desired compound precipitated. 2-Iodo-5-nitrobenzoic acid was thencollected by filtration while still cold to afford 1.73 g (49%) as a 13:2 mixture with the undesired2-iodo-3-nitrobenzoic acid isomer. The inseparable mixture was used as is in the next step.Characterization matches the data previously reported in the literature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | Following a reported procedure,19 trifluoromethanesulfonic acid (TfOH, 0.533 mL, 6.00 mmol, 1.00equiv.) was added dropwise to a stirred solution of 2-iodobenzoic acid (60) (1.49 g, 6.00 mmol, 1.00equiv.) and meta-chloroperoxybenzoic acid (mCPBA-77%, 1.48 g, 6.60 mmol, 1.10 equiv.) indichloromethane (37.5 mL) at 0 C. After 15 minutes stirring at room temperature, <strong>[57002-01-4](E)-(2-cyclohexylvinyl)boronic acid</strong> (70) (1.85 g, 12.0 mmol, 2.00 equiv.) was added in one portion at 0 C. Thereaction mixture was stirred for an additional 1 hour at room temperature, then the resulting mixture wasconcentrated in vacuo. Diethyl ether (300 mL) was added and the resulting mixture was vigorouslystirred over 30 minutes. The solid was filtered off and washed with portions of diethyl ether (5 x 50 mL).The resulting solid was dissolved in dichloromethane (50 mL) and treated with a solution of saturatedaqueous sodium bicarbonate (50 mL). The mixture was vigorously stirred for 1 hour, then the organiclayer was diluted with dichloromethane (100 mL) and the two layers were separated. The aqueous layerwas extracted with additional portions of dichloromethane (3 x 50 mL) and the combined organic layerswere washed with water (50 mL) and brine (50 mL), then dried over magnesium sulfate and filtered. Thevolatiles were removed to afford pure (E)-1-(2-cyclohexylvinyl)-1,2-benziodoxol-3(1H)-one (1n) (0.654g, 1.84 mmol, 31% yield) as a beige solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With potassium acetate; copper diacetate; copper; at 120℃;Inert atmosphere; | A mixture of a (7.9 g, 38 mmol, 1.2 eq), h (8.0 g, 32 mmol, 1.0 eq), Cu powder (0.61 g, 9.6 mmol, 0.3 eq), Cu(OAc)2 (1.7 g, 9.6 mmol, 0.3 eq), and KOAc (9.4 g, 96 mmol, 3.0 eq) in 2-pentanol (200 mL) was stirred at 120 C overnight under N2 atmosphere, and cooled to room temperature and filtered through celite. The filtrate was concentrated in vacuo Tire residue was dissolved in H2O (100 mL), acidified to pi 1 5 with 1 N HC1, and extracted with EtOAc (100 mL x 2). The organic layer was washed with brine, dried over anhydrous NacSQy and concentrated to afford the crude which was triturated with acetonitrile (30 mL), filtered to afford c (4.2 g, 40%) as a yellow solid. LC/MS: 326.0 [M+H]+. |
Tags: o-Iodobenzoic acid | 2-Iodobenzoic acid | Benzene Compounds | Iodides | Carboxylic Acids | Aryls | Fluorinated Building Blocks | Organic Building Blocks | 88-67-5
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Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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The concentration of the dissolution solution you need to prepare is mg/mL