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CAS No. : | 188815-32-9 | MDL No. : | MFCD00191851 |
Formula : | C7H4BrIO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MKJBJYCBKXPQSY-UHFFFAOYSA-N |
M.W : | 326.91 | Pubchem ID : | 5182520 |
Synonyms : |
|
Num. heavy atoms : | 11 |
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 : | 53.82 |
TPSA : | 37.3 Ų |
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) : | -6.31 cm/s |
Log Po/w (iLOGP) : | 1.88 |
Log Po/w (XLOGP3) : | 2.79 |
Log Po/w (WLOGP) : | 2.75 |
Log Po/w (MLOGP) : | 3.24 |
Log Po/w (SILICOS-IT) : | 2.86 |
Consensus Log Po/w : | 2.7 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.96 |
Solubility : | 0.0357 mg/ml ; 0.000109 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.23 |
Solubility : | 0.193 mg/ml ; 0.000589 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.55 |
Solubility : | 0.0926 mg/ml ; 0.000283 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.82 |
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: |
* 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 |
---|---|---|
99% | With sodium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 20 h; | (a) 3-Bromo-5-iodobenzoic acid methyl ester; Na2CO3 (9.7 g, 92 mmol) and MeI (5.7 ml_, 92 mmol) was added to a mixture of 3-bromo-5-iodobenzoic acid (15 g, 45.9 mmol), THF (20 mL) and DMF (75 ml.).. The mixture was stirred at rt for 20 h and concentrated. Extractive workup (EtOAc, H2O, NaHCO3 (aq, sat), brine) and concentration gave the sub-title compound. Yield: 15 g (99percent). |
99% | With sodium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 20 h; | (a) 3-Bromo-5-iodobenzoic acid methyl esterNa2CO3 (9.7 g, 92 mmol) and MeI (5.7 mL, 92 mmol) was added to a mixture of 3-bromo-5-iodobenzoic acid (15 g, 45.9 mmol), THF (20 mL) and DMF (75 mL).. The mixture was stirred at rt for 20 h and concentrated. Extractive workup (EtOAc, H2O, NaHCO3 (aq, sat), brine) and concentration gave the sub-title compound. Yield: 15 g (99percent).; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | at 0℃; for 2 h; Heating / reflux | To a solution of 3-bromo-5-iodo-benzoic acid (D7) (14.6 g, 44.7 mmol, 1 equiv) in MEOH (150 ml) at 0 C was added SOCS (3.9 ML, 53.6 mmol, 1.2 equiv). The resulting solution was refluxed for 2 h, cooled to room temperature and concentrated in vacuo. The residue was diluted with AcOEt and washed twice with 2N aqueous NAOH solution then brine, dried over MGS04 and concentrated in vacuo to give 3-bromo-5-iodo-benzoic acid methyl ester (D8a) (14.8 g, 97percent) as a pale brown solid. |
97% | at 0℃; for 2 h; Heating / reflux | To a solution of 3-bromo-5-iodo-benzoic acid (commercially available from Avocado,14.6 g, 44.7 mmol, 1 equiv) in MeOH (150 ml) at 0°C was added SOCI2 (3.9 ml, 53.6mmol, 1.2 equiv). The resulting solution was refluxed for 2 h, cooled to room temperatureand concentrated in vacua. The residue was diluted with AcOEt and washed twice with2N aqueous NaOH solution then brine, dried over MgSO4 and concentrated in vacua togive methyl 3-bromo-5-iodobenzoate (D15) (14.8 g, 97percent) as a pale brown solid whichwas used in the next step without further purification. |
96% | for 15 h; Heating / reflux | A stirred, cloudy solution of 3-bromo-5-iodobenzoic acid (10 g, 30.59 mmol) and concentrated sulfuric acid (0.60 mL) in MeOH (65 mL) was heated under reflux for 15 h. The resulting clear, light yellow solution was then allowed to cool to room temperature and was concentrated under vacuum. The residual yellow solid was dissolved in ethyl acetate (100 mL), washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound (10 g, 96percent yield) as a light yellow solid: 1H NMR (CD3OD, 500 MHz) δ ppm 3.93 (3H, s), 8.12 (1H, m), 8.15 (1H, m), 8.29 (1H, m). HPLC retention time: 2.335 min (method A). MS (ESI) (M+H)+340.00. Step 1: Preparation of methyl 3-bromo-5-iodobenzoate. A solution of 3-bromo-5-iodobenzoic acid (10 g, 30.59 mmol) and concentrated sulfuric acid (0.6 ml) in methanol (65 mL) was heated under reflux for 15 hours under nitrogen atmosphere. The resulting clear, light yellow solution was cooled to room temperature and concentrated under vacuum. The yellow solid residue was then dissolved in ethyl acetate (100 ml) and washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered and concentrated to give the methyl ester as a light yellow solid (10 g, 96 percent yield): HPLC retention time: 2.333 min (method A). MS (ESI) (M+H)+340.86. |
75% | at 0 - 20℃; for 48 h; | Synthesis of 3-bromo-5-iodo-benzoic acid methylesterTo a suspension of 3-bromo-5-iodo-benzoic acid (6.5 g, 20 mmol) in 25 mL of methanol was added SOCl2 (1.14 mL, 40 mmol) dropwise at 0° C. The mixture was then warmed to room temperature and stirred at room temperature for 2 days. The precipitates formed were collected by filtration to afford the desired product as white solid 5.12 g (75percent). LC/MS m/e calcd. for C8H6BrIO2: 341, observed (M+H)+: 342.2. |
75% | at 0 - 20℃; for 48 h; | Example 92 (IS, 2S) and (1R, 2R)-3-(2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-l,3'-indoline]- l'-yl)-5-(2-oxooxazolidin-3-yl)benzoic acidSynthesis of 3-bromo-5-iodo-benzoic acid methylesterTo a suspension of 3-bromo-5-iodo-benzoic acid (6.5 g, 20 mmol) in 25 mL of methanol was added SOCl2 (1.14 mL, 40 mmol) dropwise at 0 °C. The mixture was then warmed to room temperature and stirred at room temperature for 2 days. The precipitates formed were collected by filtration to afford the desired product as white solid 5.12 g (75percent).LC/MS m/e calcd. for C8H6BrI02: 341, observed (M+H)+: 342.2. |
75% | at 0 - 20℃; for 48 h; | Example 92; (IS, 2S) and (IR, 2R)-3-(2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-l,3'-indoline]- 1 '-yl)-5-(2-oxooxazolidin-3-yl)benzoic acid; Synthesis of 3-bromo-5-iodo-benzoic acid methylester; To a suspension of 3-bromo-5-iodo-benzoic acid (6.5 g, 20 mmol) in 25 mL of methanol was added SOCl2 (1.14 mL, 40 mmol) dropwise at 0 °C. The mixture was then warmed to room temperature and stirred at room temperature for 2 days. The precipitates formed were collected by filtration to afford the desired product as white solid 5.12 g (75percent). LC/MS m/e calcd. for C8H6BrI02: 341, observed (M+H)+: 342.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With hydrogenchloride In methanol; diethyl ether; ethyl acetate | 3-Bromo-5-cyanobenzoic Acid A mixture of 3-bromo-5-iodobenzoic acid (9.0 g) in methanol (40 mL) was treated with 1M HCl in diethyl ether (27.5 mL). The reaction was heated overnight at 40° C. The solvent was then removed in vacuo, and the residue dissolved in ethyl acetate. The organic solution was washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and concentrated to afford 8.8 g (94percent) of methyl 3-bromo-5-iodobenzoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium hydroxide In water at 100℃; for 24 h; | Step 1: 3-Bromo-5-hydroxy-benzoic acid To a solution of NaOH (12.2 g; 305.8 mmol) in 300 mL of water was added 3-bromo-5-iodo-benzoic acid (20 g, 61.2 mmol) and Cu2O (866 mg, 6.1 mmol). The reaction mixture was heated at 100° C. for 24 h. After complete consumption of the starting material, the reaction mixture was cooled to room temperature and filtered through Celite.(TM).. The filtrate was then acidified with 10percent aq. HCl and extracted into ethyl acetate. The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound as a tan solid (12.3 g, 93percent yield). HR-ES (-) calcd for C7HSO3Br [M-H]- 214.9349, observed 214.9350 |
93% | Stage #1: With sodium hydroxide In water at 100℃; for 24 h; Stage #2: With hydrogenchloride In waterAcidic aqueous solution |
To a solution of NaOH (12.2 g; 305.8 mmol) in 300 mL of water was added 3-bromo-5-iodo- benzoic acid (2Og, 61.2 mmol) and Cu2O (866 mg, 6.1 mmol). The reaction mixture was heated at 100° C for 24 h. After complete consumption of the starting material, the reaction mixture was cooled to room temperature and filtered through Celite.(TM).. The filtrate was then acidified with 10percent aq. HCl and extracted into ethyl acetate. The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound as a tan solid (12.3g, 93percent yield). HRMS calcd for C7H5O3Br [M-H]" 214.9349, observed 214.9350 |