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CAS No. : | 7745-93-9 | MDL No. : | MFCD00007195 |
Formula : | C7H6BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XFZFJQHXWJIBQV-UHFFFAOYSA-N |
M.W : | 216.03 | Pubchem ID : | 82189 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 47.93 |
TPSA : | 45.82 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.32 cm/s |
Log Po/w (iLOGP) : | 1.87 |
Log Po/w (XLOGP3) : | 3.24 |
Log Po/w (WLOGP) : | 2.67 |
Log Po/w (MLOGP) : | 2.77 |
Log Po/w (SILICOS-IT) : | 0.8 |
Consensus Log Po/w : | 2.27 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.56 |
Solubility : | 0.0597 mg/ml ; 0.000277 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.88 |
Solubility : | 0.0288 mg/ml ; 0.000133 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.02 |
Solubility : | 0.204 mg/ml ; 0.000946 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.9 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
100% | With potassium carbonate In ethanol; ethyl acetate | g. 3-bromo-4-methylaniline. To a solution of 2-bromo-4-nitrotoluene (50 g, 0.231 mol in ethylacetate (330 mL) and Ethanol (150 mL) was added Tin(II)chloride dihydrate (208 g, 0.924 mol) portionwise. The reaction mixture was stirred at room temperature overnight. The solution was then treated with potassium carbonate until pH=7 and filtered over celite. The filtrate was washed with water, aqueous NaHCO3, water and brine, dried (Mg2SO4), filtered and evaporated to give 42.71 g (100percent) of 3-bromo-4-methylaniline. 1H NMR (300 MHz; CDCl3): 2.27 (s, 3 H), 3.57 (br s, 2 H), 6.54 (dd, J=2.7 Hz and 8.1 Hz, 1 H), 6.90 (d, J=2.1 Hz, 1 H), 6.98 (d, J=8.1 Hz, 1 H). |
100% | With potassium carbonate In ethanol; ethyl acetate | g. 3-bromo-4-methylaniline. To a solution of 2-bromo-4-nitrotoluene (50 g, 0.231 mol in ethylacetate (330 mL) and Ethanol (150 mL) was added Tin(II)chloride dihydrate (208 g, 0.924 mol) portionwise. The reaction mixture was stirred at room temperature overnight. The solution was then treated with potassium carbonate until pH=7 and filtered over celite. The filtrate was washed with water, aqueous NaHCO3, water and brine, dried (Mg2SO4), filtered and evaporated to give 42.71 g (100percent) of 3-bromo-4-methylaniline. 1H NMR (300 MHz; CDCl3): 2.27 (s, 3 H), 3.57 (br s, 2 H), 6.54 (dd, J=2.7 Hz and 8.1 Hz, 1 H), 6.90 (d, J=2.1 Hz, 1 H), 6.98 (d, J=8.1 Hz, 1 H). |
100% | With potassium carbonate In ethanol; ethyl acetate | (4) 3-bromo-4-methylaniline. To a solution of 2-bromo-4-nitrotoluene (50 g, 0.231 mol in ethylacetate (330 mL) and Ethanol (150 mL) was added Tin(II)chloride dihydrate (208 g, 0.924 mol) portionwise. The reaction mixture was stirred at room temperature overnight. The solution was then treated with potassium carbonate until pH=7 and filtered over celite. The filtrate was washed with water, aqueous NaHCO3, water and brine, dried (Mg2SO4), filtered and evaporated to give 42.71 g (100percent) of 3-bromo-4-methylaniline. 1H NMR (300 MHz; CDCl3): 2.27 (s, 3 H), 3.57 (br s, 2 H), 6.54 (dd, J=2.7 Hz and 8.1 Hz, 1 H), 6.90 (d, J=2.1 Hz, 1 H), 6.98 (d, J=8.1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | Stage #1: With chromium(VI) oxide; sulfuric acid; acetic anhydride In acetic acid at 5 - 10℃; for 1.5 h; Cooling with ice Stage #2: With sulfuric acid In ethanol; water for 1 h; Reflux |
2-Bromo-1-methyl-4-nitrobenzene (15.0 g, 69.4 mmol) was dissolved inacetic acid (112 mL) and acetic anhydride (105 mL, 1,113 mmol). The mixture was placed in an ice-water bath and concentrated sulfuric acid (15 mL, 281 mmol) was added slowly. Chromium(VI) oxide (34.7 g, 347 mmol) was then added in portionswhile maintaining the temperature of the reaction mixture between 5-10 ° C. The reaction mixture was stirred in an ice-bath for 1.5 h. The internal temperaturehovered between 5-10 °C. It was necessary to monitor the reaction temperature due to a delayed exotherm. At one point it was necessary to place the reaction mixture in an ice-acetone bath for a period of time to keep the temperature from exceeding 10°C. The contents of the flask were then poured into a 2 liter Erlenmeyer flask containing some ice. Cold water was then added to bring the total volume to 1500mL. The solid was collected on a Buchner funnel. The solid was washed with cold water until it was nearly colorless. The solid was suspended in cold 2percent aqueous Na2CO3 solution (100 mL) and was thoroughly stirred. The solid was collected on a filter and was washed with cold water and partially dried on the Buchner funnel to give 8.3 grams of the diacetate intermediate.A mixture of 8.3 g of crude diacetate intermediate, ethanol (16 mL), water (16 mL), and conc. H2S04 (2.4mL) was heated at reflux for 1 h. The mixture was cooled to room temperature and the mixture was transferred to a separatory funnel containing saturated aqueous K2C03 (50 mL) solution. A fluffy solid formed. It was subsequently determined that this solid was not the product. The aqueous layer wasextracted with ethyl acetate (4 x 50 mL). The combined organic layers were washed with brine (25 mL), dried over MgSO4, filtered, and concentrated. The solid was purified by colunm chromatography on silica gel (5percent —* 15percent ethyl acetate in hexanes) to afford 2-bromo-4-nitrobenzaldehyde (1 .41 g, 9percent yield) as a colorless fluffy solid: ‘H NMR (400 MHz, CDC13) ö 10.41 (s, 1 H), 8.51 (d, J=2.0 Hz, 1 H),8.25 (dd, J=8.4, 2.1 Hz, 1 H), 8.06 (d, J8.6 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | at 80℃; for 24 h; | A mixture of compound 1 (250.0 g, 1.16 mol), Zn(CN)2 (135.0 g, 1.16 mol) and Pd(PPh3)4 (25 g, 0.02 mol) in dry DMF (1500 mL) was stirred at 80 °C for 24 hours under N2. TLC (petroleum ether: ethyl acetate = 10:1) showed the reaction was complete, then the mixture was poured into toluene (1500 mL) and washed with 2 N NH3 H2O (800 mLx2). The aqueous layer was extracted with toluene (800 mLx2). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give crude product, which was purified by column chromatography (first petroleum ether, then petroleum ether: ethyl acetate 10:1) to afford compound 2 (25.5 g, yield: 42percent) as a grey solid and recover compound 1 (170 g) as yellow solid.1H NMR (300 MHz, CDCI3): δ 8.46-8.47 (d, J = 3.0 Hz, 1 H), 8.31-8.34 (dd, J = 9.0 Hz, 1 H), 7.53-7.56 (d, J = 9.0 Hz, 1 H), 2.68 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With N-Bromosuccinimide; dibenzoyl peroxide In benzene for 16 h; Reflux | Bromine (2.75 mL, 8.58 g, 53.6 mmol) was added dropwise to a stirred solution of m-anisaldehyde(6.06 g, 44.6 mmol) in AcOH (10 mL) in 3 minutes to bring the solution to gentle reflux. After 24 hours the reaction mixture was poured into water (130 mL). The precipitate was filtered, washed with water and dissolved in EtOAc (60 mL). This solution was washed with water (50 mL), brine (50 mL), dried over Na2SO4 and concentrated on a rotary evaporator. The yellow residue was recrystallized from hexane to give bromobenzaldehyde SI-1c (8.05 g, 37.4 mmol, 84percent) as beige solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.1% | With potassium permanganate In pyridine; water for 5 h; Reflux | To a mixture of 2-bromo-4-nitrotoluene (25g, 116mmol), pyridine (100mL) and water (200mL) was added KMnO4 (102g, 642mmol) in portions. After the mixture was refluxed for 5h, an additional amount of KMnO4 (27.5g, 174mmol) was added. The mixture was refluxed and stirred for overnight, then filtered over celite. The filtrate was acidified with concentrated HCl (110mL), extracted with EtOAc (600mL), dried over anhydrous Na2SO4, and evaporated under vacuum to give compound 19 as a solid (19.4g, 68.1percent yield). 1H NMR (400MHz, CD3OD): δ 8.43 (d, J=2.1Hz, 1H), 8.18 (dd, J=8.5, 2.1Hz, 1H) and 7.86 (d, J=8.5Hz, 1H) ppm; mp: 153–155°C. |
66% | With pyridine; potassium permanganate In water at 70℃; for 8 h; Heating / reflux | (a) Synthesis of 2-bromo-4-nitrobenzoic acid Water (40 ml) was added to a solution of 2-bromo-4-nitrotoluene (4.41 g, 20.0 mmol) in pyridine (20 ml), and the resulting mixture was heated at 70°C. Potassium permanganate (19.0 g, 120 mmol) was added thereto over a period of 40 minutes and the resulting mixture was refluxed for 8 hours. After completion of the reaction, the suspension thus obtained was filtered. The filtrate was acidified with 6N-hydrochloric acid under ice-cooling. The resulting suspension was filtered to obtain 2-bromo-4-nitrobenzoic acid (1.63 g). Hydrochloric acid was added to the filtrate, followed by extraction with ethyl acetate and chloroform. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated to obtain 2-bromo-4-nitrobenzoic acid (1.61 g, total amount 3.24 g, 66percent). |
28% | With sodium dichromate; sulfuric acid In acetic acid at 75 - 110℃; for 3 h; | Compound 21 used in the preparation of compound 24 was prepared as follows. Sodium dichromate dihydrate (151 gm) was added to glacial acetic acid (575 ml) followed by 2-bromo-4-nitro-toluene (49.7 gm). To this solution was added dropwise sulphuric acid (175 ml) at such a rate to maintain the temperature between 75-85° C. This mixture was heated to 100-110° C. for 3 h cooled to 50° C. and poured onto ice (1 litre). The aqueous phase was extracted with ethyl acetate, the organic layer back extracted with Aqueous sodium hydroxide solution and the resulting basic aqueous layer acidified with concentrated hydrochloric acid. The precipitated solid was filtered, washed with water and air dried to give 15.72 gm (28percent) of 2-bromo-4-nitro-benzoic acid (compound 26) as a white solid. NMR H1NMR (CDCl3) δ: 7.42 (1H, d), 8.08 (1H, q), 8.42 (1H, d) |
51% | With hydrogenchloride In diethyl ether; sulfuric acid; water | 2-bromo-4-nitrobenzoic Acid To a solution of 2-bromo-4-nitrotoluene (7.0 g, 32 mmol) that was dissolved in if sulfuric acid (98percent, 50 mL) and placed in a water bath to maintain ambient temperature was added dropwise a solution of chromium trioxide (7.5 g, 75 mmol) in water (8 mL). Following addition, the mixture was poured onto 200 mL of ice, the precipitate was collected and washed with water (1*100 mL). The crude product was taken up in diethyl ether (50 mL), extracted with aqueous NaHCO3solution (2*25 mL). The combined bicarbonate layers were acidified by the addition of 12M HCl, extracted with diethyl ether (2*25 mL). The second set of diethyl ether layers was washed with brine (1*25 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to provide the titled compound 4.0 g (51percent). 1H NMR (300 MHz, d6-DMSO) δ8.48 (d, 1H, J=2.4), 8.28 (dd, 1H, J=2.0, 8.5), 7.95 (d, 1H, J=8.5); MS (ESI) m/z=244, 246 (M-H). |
72 g | With pyridine; potassium permanganate In water at 80℃; | Intermediate 10A. 2-Bromo-4-nitro-benzoic acid: To a warm (80 °C) solution of pyridine (500 mL) and water (1 L) was added 4-nitro-2-bromo toluene (100 g, 0.46 mol). The resulting suspension was stirred until it became a clear solution. To the above reaction mixture was then added KMn04 (600 g, 3.8 mol) in portions over 1.5 h and stirring was continued overnight. The reaction mixture was then cooled to rt and then 10percent aqueous NaOH (200 mL) was added. After 15 min, the reaction was filtered to remove the solids. The solids were then rinsed with 10percent aqueous NaOH (5x100 mL). The filtrate was extracted with MTBE (3x250 mL). The clear aqueous layer was cooled to 10 °C and then it was acidified with concentrated HC1. The aqueous layer was again extracted with MTBE (4x500 mL). The organic layers were combined, dried over Na2S04, filtered and concentrated to afford 72 g of Intermediate 10A. 1H NMR (400 MHz, DMSO-d6) δ 7.96 (d, J = 8 Hz, 1H), 8.28 - 8.48 (m, 1H), 8.49 (d, J = 2.4 Hz, 1H), 14.1 (br. s, 1H) ppm. |
72 g | With potassium permanganate In pyridine; water | [00355] Intermediate 18 A. 2-Bromo-4-nitro-benzoic acid: To a warm (80 °C) solution of pyridine (500 mL) and water (1 L) was added 4-nitro-2-bromo toluene (100 g, 0.46 mol). The resulting suspension was stirred until it became a clear solution. To the above reaction mixture was then added KMn04 (600 g, 3.8 mol) in portions over 1.5 h and stirring was continued overnight. The reaction mixture was then cooled to rt and then 10percent aqueous NaOH (200 mL) was added. After 15 min, the reaction was filtered and the solid was rinsed with 10percent> aqueous NaOH (5x100 mL). The filtrate was extracted with MTBE (3x250 mL). The clear aqueous layer was cooled to 10 °C and then it was acidified with concentrated HC1. The aqueous layer was again extracted with MTBE (4x500 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford 72 g of Intermediate 18A. 1H NMR (400 MHz, DMSO-d6) δ 7.96 (d, J= 8 Hz, 1H), 8.28 - 8.48 (m, 1H), 8.49 (d, J= 2.4 Hz, 1H), 14.1 (br. s, lH) ppm. |
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