Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 5344-78-5 | MDL No. : | MFCD00051511 |
Formula : | C7H6BrNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KCOBIBRGPCFIGF-UHFFFAOYSA-N |
M.W : | 232.03 | Pubchem ID : | 79288 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 49.46 |
TPSA : | 55.05 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) : | -5.81 cm/s |
Log Po/w (iLOGP) : | 1.7 |
Log Po/w (XLOGP3) : | 2.68 |
Log Po/w (WLOGP) : | 2.37 |
Log Po/w (MLOGP) : | 2.18 |
Log Po/w (SILICOS-IT) : | 0.35 |
Consensus Log Po/w : | 1.86 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.2 |
Solubility : | 0.145 mg/ml ; 0.000624 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.49 |
Solubility : | 0.0754 mg/ml ; 0.000325 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.77 |
Solubility : | 0.399 mg/ml ; 0.00172 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.15 |
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 |
---|---|---|
75% | at 160℃; for 2 h; | 3-Nitro-4-bromoan-isole (5.00 g, 21.54 mmol) was dissolved in anhydrous DMF and CuCN (2.89 g, 32.32 mmol) was added. The mixture was heated at 160 °C for 2 h. After cooling it was poured into crushed ice and a precipitate was formed, which was filtered and dried under vacuum. The greenish solid obtained was dissolved in CHCl3 and the solution was filtered. The solvent removal of the filtrate gave a yellow solid (2.88 g, 75percent); mp 129-130 °C (lit. [9] : 129-131 °C); IR (KBr) νmax (cm-1): 3103, 2230 (CN), 1616, 1529, 1500, 1443, 1348, 1311, 1285, 1248, 1188, 1067, 1020, 899, 840, 808; 1H NMR (300 MHz, CDCl3): δ 7.84-7.79 (m, 2H, H-3 and H-6), 7.28 (dd, 1H, J1 = 2.4 Hz, J2 = 9.0 Hz, H-5), 3.99 (s, 3H, OCH3); 13C NMR (75 MHz, CDCl3): δ 163.2, 150.1, 136.6, 119.9, 115.2, 111.1, 99.4, 56.5; MS (ESI) m/z (percent): 179.1 (100) [M + H]+. Anal. calcd for C8H6N2O3: C, 53.94; H, 3.39; N, 15.73. Found: C, 54.11; H, 3.40; N, 15.75. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: With hydrogen bromide; sodium nitrite In water at 0 - 10℃; for 1.16667 h; Stage #2: With copper(I) bromide In water at 0 - 60℃; for 3 h; Heating / reflux |
A solution of sodium nitrite (11.8 g) in water (28 mL) was added dropwise over 0.5 h to a solution of the nitroaniline (125 mmol) in 40percent. hydrobromic acid (110 g) at 10° C. The reaction mixture was maintained for 40 min at 0-10° C. and was filtered. The filtrate was added dropwise over 1 h to a 0° C., purple solution of copper (I) bromide (209 mmol) in hydrobromic acid (74 mL). The reaction mixture was allowed to warm to and maintained at rt for 30 min, was maintained at 60° C. for 0.5 h, and was heated at reflux for 1 h. The reaction mixture was partitioned between water (2.0 L) and dichloromethane (600 mL) and the aqueous layer was further extracted with dichloromethane (300 mL). The combined organic layers were washed with 10percent sodium hydroxide (200 mL), water (600 mL), 10percent hydrochloric acid (300 mL), and water (600 mL), dried (magnesium sulfate) and concentrated to provide the nitrobromide in 83percent yield as a yellow oil. |
83% | With tert.-butylnitrite; tetrabutylammomium bromide; copper(I) bromide; camphorsulfonic acid In acetonitrile at 20℃; for 24 h; | General procedure: Catalytic amounts of copper bromide (1 mol percent) were added to a solution of aniline (2.5 mmol) in acetonitrile (30 ml), camphorsulfonic acid (3.0 mmol), sodium nitrite or tert-butyl nitrite (3.0 mmol), and tetrabutylammonium bromide (5.0 mmol). The reaction mixture was stirred at 60 °C for 24 h (Tables 1 and 2). The evolution of N2 was immediately observed. The solvent was removed by a rotary evaporator after completion of the reaction (confirmed by β-naphthol test and TLC). The solid was washed with water and extracted with CH2Cl2. The resulting solution was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The pure product was then collected by column chromatography using hexane/dichloromethane as eluting solvents. Physical and 1H NMR data were identical to those of a commercially available sample of analytical purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium bromide In dimethyl sulfoxide at 160℃; for 24 h; Schlenk technique | Silak reaction tube equipped with a magnetic stirrer was charged with 6.2 mg of silver sulfate,36.3 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline,39.4 mg of 2-nitro-4-methoxybenzoic acid and 30.9 mg of sodium bromide4 mL of dimethyl sulfoxide. Heat 160 ° C in the presence of oxygenReaction for 24 hours. After the reaction was completed, distilled water was added to quench the reaction,Extraction with ethyl acetate 3 times, each time 10mL,The combined organic phases are concentrated,31.1 mg of 2-nitro-4-methoxybromobenzene was obtained in a yield of 67percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With iron; ammonium chloride In ethanol; water for 2 h; Reflux | 1-Bromo-4-methoxy-2-nitrobenzene (1.71g, 7.2 mmol, 1 equiv.) was dissolved in EtOH (7 mL) and H2O (5 mL). Iron powder (2.00 g,35.7 mmol, 5 equiv.) and NH4Cl (1.53 g, 28.6 mmol, 4 equiv.) were added to the solution. The solution was heated to reflux for 2 h. The black organic phase was washed with diethyl ether(4 x 100 mL). This yielded 2-bromo-5-methoxyaniline (95percent) as a green substance, with data as reported.7 At 0 °C a solution of the crude 2-bromo-5-methoxyaniline (1.50 g, 7.4 mmol, 1equiv.) in conc. HCl (7 mL) was treated dropwise with aq. NaNO2 (0.5 g, 7.2 mmol, 1 equiv.)in deionized H2O (5 mL). Stirring was continued at 0 °C for 5 h resulting in the formation ofthe diazonium salt. In a separate flask, at 0 °C, H2O (8 mL) was treated with thionyl chloride(2.2 mL, 30.3 mmol, 4 equiv.). Stirring continued at 0 °C for 1 h. The aqueous phase was washed with ethylacetate (6 x 50 mL). The combined phases were dried over MgSO4. Solvent removal followed by column chromatography (c-Hex-EtOAc; 5:1) yielded S5 (1.50 g, 46percent) asa yellow oil. Rf = 0.3 (c-Hex-EtOAc; 5:1) with data as reported.8 |
91% | at 50℃; for 3.5 h; | Step i :To a 1 L flask equipped with a mechanical stirrer is added 55a (30 g, 129 mmo.) in acetic acid (300 ml_). To this mixture is added iron powder (14.4 g, 258 mmol) slowly in aliquots. The mixture is heated at 500C for 2 h before an additional 7.2 g (129 mmol) of iron powder is slowly added. After 1.5 h at 500C, the conversion to the aniline is complete. The solution is cooled to RT and diluted with 500 ml_ of EtOAc before being filtered through Celite. The filtrate is concentrated and the crude product is partitioned between EtOAc (1 L) and 200 mL of water. The mixture is vigorously shaken and the organic phase is washed with 200 mL of brine, dried over MgSO4, filtered and concentrated to give aniline 55b (23.7 g, 91 percent) as a brown oil which is used directly in the next step. |
86% | With hydrogen In ethanol at 20℃; for 4 h; | A mixture of 1-bromo-4-methoxy-2-nitro-benzene (10 g, 43 mmol) and Raney Ni (5 g) in ethanol (100 mL) was stirred under H2 (1 atm) for 4 h at room temperature. Raney Ni was filtered off and the filtrate was concentrated under reduced pressure. The resulting solid was purified by column chromatography to give 2-bromo-5-methoxy-phenylamine (7.5 g, 86percent). |
86% | With hydrogen In ethanol at 20℃; for 4 h; | A mixture of 1-bromo-4-methoxy-2-nitro-benzene (10 g, 43 mmol) and Raney Ni (5 g) in ethanol (100 mL) was stirred under H2 atm) for 4 h at room temperature. Raney Ni was filtered off and the filtrate was concentrated under reduced pressure. The resulting solid was purified by column chromatography to give 2-bromo-5-methoxy-phenylamine (7.5 g, 86percent). |
52% | Stage #1: at 20℃; for 2 h; Stage #2: With potassium carbonate In water |
Example I-XIPreparation of Compound 314General Procedure I-CSA mixture of 4-bromo-3-nitroanisole (5 g, 21.6 mmol) and Fe (9.7 g, 0.17 mol) in 30 mL of acetic acid was stirred at r.t for 2 h. After removal of the solvent under reduced pressure, the brown residue was taken up in 100 mL of water and treated with 10percent of aq. K2CO3 until pH 10. The mixture was extracted with EtOAc (150 mL.x.2) and the combined organic extracts were separated, dried over MgSO4, and concentrated to afford compound I-XIa (3 g, yield: 52percent). MS (ESI) m/z (M+H)+ 203. |
48% | With acetic acid; zinc In ethanol at 20℃; | To a suspension of Zn (3.92 g, 60.3 mmol) in EtOH (80 mL) was added HOAc (3 mL), followed by solution of compound 5-1 (2.0 g, 8.6 mmol) in EtOH (20 mL) at rt. After stirring at rt overnight, the reaction mixture was filtered. The filtrate was concentrated and the residue was diluted with EtOAc (150 mL). The mixture was washed with water (200 mL) and brine (100 mL) and dried with anhydrous Na2S04. The solvent was removed and the residue was purified by silica gel column chromatography (Petroleum ether /EtOAc = 19/1 (v/v)) to give compound 5-2 (1.15 g, 48percent yield) as a yellow oil. LC-MS (ESI): mlz 202 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With acetic acid In water | (i) Preparation of 2-bromo-5-methoxyaniline 4-Bromo-3-nitroanisole (10 g, 43 mmol) and iron powder (21.72 g, 385 mmol) were stirred in a mixture of water (10 mL) and acetic acid (100 mL) for 1.5 h. The solvent was removed in vacuo, the brown residue was taken up in water (200 mL) and treated with 10percent aq K2CO3 until pH 10. The mixture was extracted with EtOAc (4*150 mL) and the combined organic extracts were dried (MgSO4) and evaporated to give the desired aniline (5.0 g, 57percent) as a brown oil; δH (CDCl3, 400 MHz) 3.72 (3H, s), 4.05 (2H, br), 6.22 (1H, dd), 6.32 (1H, d), 7.26 (1H, d); MS m/z (TS+) 202, 204 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With boron tribromide In dichloromethane; ethyl acetate | Example 48 2-Bromo-3-isopropoxynitrobenzene BBr3 (1 M in CH2 Cl2, 77 mL, 77 mmol) was added dropwise, over 1 h, to a stirred solution of 4-bromo-3-nitroanisole (5.0 g, 22 mmol) in 30 mL CH2 Cl2 at -70° C. under nitrogen. The resulting deep burgundy-colored reaction was stirred overnight (23 h) and then poured onto 300 g crushed ice. EtOAc (250 mL) was added and the organic fraction washed with brine (250 mL), dried (MgSO4) and concentrated in vacuo to 5.06 g of a yellow-brown solid. Purification by column chromatography (EtOAc/hexane, gradient elution 5:95 to 15:85) afforded 3.77 g (79percent) of 2-bromo-3-nitrophenol as a yellow solid: TLC (EtOAc/hesane 20:80) Rf =0.12; HPLC (Tr =12.2); 1 H-NMR (CDCl3) δ 5.57 (s, 1H, --OH), δ 6.95 (dd, J=8 Hz, J=3 Hz, 1H), δ 7.36 (d, J=3 Hz, 1H), δ 7.58 (d, J=8 Hz, 1H); MS m/z (relative intensity) 218 (MH+, 100), 220 (MH+ +2.56). Anal. Calcd. for C6 H4 BrNO3: C, 33.06; H, 1.85; N, 6.42; Br, 36.65 Found: C, 33.14; H, 1.86; N, 6.38; Br, 36.57. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: With boron tribromide In dichloromethane at -78 - 20℃; for 31 h; Stage #2: With water In dichloromethane at 0℃; |
A solution of boron tribromide (250 mmol) in dichloromethane (200 mL) was added drop wise over 1 h to a solution of the nitrobromide (100 mmol) in dichloromethane (250 mL) at -78° C. The reaction mixture was allowed to warm to rt and was maintained for 30 h. The reaction mixture was cooled to 0° C., quenched with water (300 mL) and the aqueous layer was extracted with ethyl acetate (2*300 mL). The combined organic layers were washed with saturated sodium bicarbonate (2*300 mL), dried (magnesium sulfate), and concentrated to provide the nitrophenol in 87percent yield as a brown crystalline solid. |
87% | Stage #1: With boron tribromide In dichloromethane at -78 - 20℃; for 31 h; Stage #2: With water In dichloromethane at 0℃; |
A solution of boron tribromide (250 mmol) in dichloromethane (200 mL) was added drop wise over 1 h to a solution of the nitrobromide (100 mmol) in dichloromethane (250 mL) at -78 0C. The reaction mixture was allowed to warm to rt and was maintained for 30 h. The reaction mixture was cooled to 0 0C, quenched with <n="79"/>>yater (300 mL) and the aqueous layer was extracted with ethyl acetate (2 x 300 mL). The combined organic layers were washed with saturated sodium bicarbonate (2 x 300 mL), dried (magnesium sulfate), and concentrated to provide the nitrophenol in 87percent yield as a brown crystalline solid. |
79% | Stage #1: With boron tribromide In dichloromethane at -78 - 20℃; for 50 h; Inert atmosphere Stage #2: With water In dichloromethane at 20℃; for 3 h; |
Step 1 . Synthesis of 4-bromo-3-nitrophenol (C3). 1 -Bromo-4-nnethoxy- 2-nitrobenzene (170 g, 0.73 mol) was dissolved in dichloromethane (1 .5 L) in a 5-liter, 3-necked flat-bottomed flask equipped with a thermometer, pressure-equalizing dropping funnel and exhaust gas scrubber (1 M aqueous sodium hydroxide). The solution was cooled to -78 °C under argon. Boron tribromide (176 ml_, 1 .86 mol) was dissolved in cold dichloromethane (1 .6 L, 0 °C); this was added to the cooled reaction via the dropping funnel over 2 hours. An exotherm brought the temperature to -55 °C. At the completion of the addition, the cooling bath was removed and the reaction was allowed to warm to RT and stir for 48 hours.The reaction mixture was added to cold water (2.0 L, ice/water bath) over 4 hours via a dropping funnel, maintaining the internal temperature below 20 °C. A scrubber (1 M aqueous sodium hydroxide) was used to prevent release of the HBr gas that was formed. The quenched mixture was stirred at RT for an additional hour, at which time the phases were separated and the aqueous layer was extracted with EtOAc (2.0 L); the combined organic layers (dichloromethane and EtOAc) were washed with saturated aqueous sodium bicarbonate solution (2 x 1 .2 L; lower phase was the organic layer), then with brine (1 L, lower phase was the aqueous layer), dried over magnesium sulfate and concentrated in vacuo. The residue was suspended in dichloromethane (320 ml_) and slurried overnight, and the solid was collected by filtration. The solid was dissolved in aqueous sodium hydroxide solution (2.0 M, 500 mL) and extracted with dichloromethane (500 mL). The dichloromethane layer was then extracted with aqueous sodium hydroxide solution (250 mL), and the combined aqueous layers were acidified to pH 2 with aqueous HCI (1 .0 M, 790 mL). The precipitated phenol was filtered and dried under vacuum at 40 °C for 18 hours to provide C3 as a solid. Yield: 125.5 g, 0.5757 mol, 79percent. 1H NMR (400 MHz, CD3OD) δ 6.95 (dd, J=8.8, 2.9 Hz, 1 H), 7.24 (d, J=2.9 Hz, 1 H), 7.57 (d, J=8.8 Hz, 1 H). |
31% | With boron tribromide In dichloromethaneReflux | To a solution of 1-bromo-4-methoxy-2-nitrobenzene (20 g, 82 mmol) in DCM (800 mL) was added dropwise BBr3 (19 mL, 207 mmol) in DCM (120 mL). The resulting mixture was heated to reflux overnight. The mixture was cooled in ice-water and was diluted by addition of water. Then the mixture was washed with saturated NaHCO3 and brine. The organic phase was dried over Na2SO4, concentrated under reduced pressure to give a residue, which was purified by column chromatography on silica gel to provide 4-bromo-3-nitrophenol (6 g, 31percent) as a solid: ‘H NMR (CDC13): 3 7.57 (d, J = 8.8 Hz, 1H), 7.35 (d, J= 2.6 Hz, 1H), 6.94 (dd, J= 2.9, 8.6 Hz, 1H), 5.90 (br., 1H). |
[ 10172-35-7 ]
2-Bromo-4-methoxy-6-nitroaniline
Similarity: 0.91
[ 16618-67-0 ]
1-Bromo-3-methoxy-5-nitrobenzene
Similarity: 0.90
[ 33696-00-3 ]
4-Bromo-1-methoxy-2-nitrobenzene
Similarity: 0.89
[ 5197-28-4 ]
2-Bromo-1-methoxy-4-nitrobenzene
Similarity: 0.88
[ 10172-35-7 ]
2-Bromo-4-methoxy-6-nitroaniline
Similarity: 0.91
[ 16618-67-0 ]
1-Bromo-3-methoxy-5-nitrobenzene
Similarity: 0.90
[ 33696-00-3 ]
4-Bromo-1-methoxy-2-nitrobenzene
Similarity: 0.89
[ 5197-28-4 ]
2-Bromo-1-methoxy-4-nitrobenzene
Similarity: 0.88
[ 10172-35-7 ]
2-Bromo-4-methoxy-6-nitroaniline
Similarity: 0.91
[ 16618-67-0 ]
1-Bromo-3-methoxy-5-nitrobenzene
Similarity: 0.90
[ 33696-00-3 ]
4-Bromo-1-methoxy-2-nitrobenzene
Similarity: 0.89
[ 5197-28-4 ]
2-Bromo-1-methoxy-4-nitrobenzene
Similarity: 0.88
[ 500298-30-6 ]
1-Bromo-3-methoxy-2-nitrobenzene
Similarity: 0.87
[ 10172-35-7 ]
2-Bromo-4-methoxy-6-nitroaniline
Similarity: 0.91
[ 16618-67-0 ]
1-Bromo-3-methoxy-5-nitrobenzene
Similarity: 0.90
[ 33696-00-3 ]
4-Bromo-1-methoxy-2-nitrobenzene
Similarity: 0.89
[ 5197-28-4 ]
2-Bromo-1-methoxy-4-nitrobenzene
Similarity: 0.88