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CAS No. : | 5228-61-5 | MDL No. : | MFCD09056836 |
Formula : | C6H5BrN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RMIFLIVHJLREFJ-UHFFFAOYSA-N |
M.W : | 217.02 | Pubchem ID : | 5314766 |
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 : | 47.37 |
TPSA : | 71.84 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.27 cm/s |
Log Po/w (iLOGP) : | 1.42 |
Log Po/w (XLOGP3) : | 1.9 |
Log Po/w (WLOGP) : | 1.95 |
Log Po/w (MLOGP) : | 1.05 |
Log Po/w (SILICOS-IT) : | -0.33 |
Consensus Log Po/w : | 1.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.72 |
Solubility : | 0.413 mg/ml ; 0.0019 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.03 |
Solubility : | 0.202 mg/ml ; 0.00093 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.28 |
Solubility : | 1.14 mg/ml ; 0.00527 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.19 |
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 |
---|---|---|
84% | With O-Methylhydroxylamin; potassium <i>tert</i>-butylate In 1,2-dimethoxyethane; N,N-dimethyl-formamide at 0 - 20℃; for 4.83333 h; | Example 14a; 7V-(2-Amino-5-(lH-pyrrol-2-yl)phenyl)-4-methoxybenzamide (147); Scheme 14;;Example 14a; ;<n="111"/>Step 1 : 5-Bromo-2-nitrobenzenamine (142); [0745] To a solution of potassium tert-butoxide (21.92 g, 195 mmol) and copper (I) chloride(2.36 g, 23.8 mmol) in ethyleneglycol dimethylether (170 mL), stirred at 0 0C under nitrogen, a solution of l-bromo-4-nitrobenzene (141, 8.69 g, 43.0 mmol) in DMF (45 mL) was added drop wise over 50 min. After complete addition the cooling bath was removed and the mixture was allowed to stir at room temperature for 4 h, diluted with DCM, washed with aqueous NH4Cl, dried over MgSO4, filtered and concentrated to give compound 142 (7.85 g, 84percent yield).[0746] 1H NMR (CDC13) δ (ppm): 7.98 (d, J= 9.2 Hz, IH), 7.02 (d, J= 2.0 Hz, IH), 6.82 (dd,J= 9.2, 2.0 Hz, IH), 6.12 (bs, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With ammonium hydroxide In dimethyl sulfoxide at 100℃; for 20 h; Autoclave | 13.53 g of 2,4-dibromonitrobenzene (2) dissolved in 20 mL of DMSO is put in a steal autoclave. 51 mL of an aqueous ammonium hydroxide solution (32 percent) is added, the autoclave is equipped with a magnetic stir bar, sealed and heated to 100 °C for 20 hours. After cooling to room temperature the reaction mixture is given into water, the precipitate is sucked off, washed several times with water and recrystallised from a mixture of DIPE/MeOH (1:1) to give 9.87 g (45.5 mmol) of the desired product as orange crystals (94 percent). Melting point: 148-150 °C. 1H-NMR (200 MHz, DMSO-d6): 7.89 (d, 3J = 9.2 Hz, 1H), 7.53 (s, 2H), 7.25 (d, 4J = 2.0 Hz, 1H), 6.76 (dd, 4J = 2.0 Hz, 3J = 9.2 Hz, 1H). |
92% | With ammonia In water; dimethyl sulfoxide at 100℃; for 18 h; | In a sealed reaction tube, add cautiously 6 [ML] of an aqueous solution of ammonia [(32percent)] to a solution of 2,4-dibromonitrobenzene (1,6 g) in 2 [ML] of DMSO. Stir for 18 hours at [100°C] and cool to room temperature. Pour the heterogeneous mixture into water and filter the title compound (1.1 [G,, 92percent)] as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With ammonia In methanol at 20℃; for 18 h; | 5-Bromo-2-nitro aniline 2-Fluoro-4-bromo-1-nitrobenzene (0.5 g, 2.2 mmol) was added to methanolic ammonia (10 mL) and stirred at r.t. for 18 h. The reaction mixture was then concentrated in vacuo and the residue was triturated with isohexane, yielding the title compound (0.48 g, 97percent) as a yellow solid. δH (d6-DMSO) 7.88 (d, J 8.8 Hz, 1H), 7.53 (br s, 2H), 7.25 (d, J 3.0 Hz, 1H), 6.75 (dd, J 9.2, 2.0 Hz, 1H). |
91% | With ammonia In methanol at 0 - 20℃; for 12 h; Sealed tube | To a solution of 4-bromo-2-fluoro-1-nitrobenzene (5 g, 22.7 mmol) in MeOH (5 mL), maintained at 0°C in a sealed tube, was added methanolic ammonia (15 mL). The reaction mixture was stirred at room temperature for 12 h, then concentrated. The crude residue was triturated with pentane and Et20 to afford the title compound (4.5 g, 91percent), which was used for the next step without any further purification. H (400 MHz, CD3OD) 7.93 (d,J9.1 Hz, 1H), 7.18 (d,J2.1 Hz, 1H), 6.74 (dd,J9.2, 2.1 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium <i>tert</i>-butylate; copper(l) chloride In DMF (N,N-dimethyl-formamide); 1,2-dimethoxyethane at 0 - 20℃; for 4.71667 h; | Step 1. 5-BromO-2-nitro-phenylamine (2); [0176] To a solution of potassium tert-butoxide (14.5 g; 129.2 MMOL) and copper (L) chloride (301 mg ; 3.04 MMOL) in ETHYLENEGLYCOL DIMETHYLETHER (120 mL), stirred at 0°C under nitrogen, a solution of 1-bromo-4-nitro-benzene (1,6. 141 g; 30.4 MMOL) and 0-methyl-hydroxylamine hydrochloride (3.174 g; 38 MMOL) in N, NDIMETHYLFORMAMIDE (65 mL) was added drop wise over 103 min, the cooling bath was removed and the mixture was allowed to react at room temperature for 3h, diluted with ethyl acetate (600 mL) and washed with saturated aqueous ammonium chloride. The organic layer was dried (MGS04), filtered and concentrated. After purification by flash chromatography (eluent 25percent ethyl acetate in hexane), 4.96 g (75percent yield) of compound 2 were obtained. [0177] H NMR: (400.2 MHz, CDCI3) 8 (ppm): 7.98 (d, J=9.24, 1H); 7.02 (d, J=1. 98,1H) ; 6.82 (dd, J=1.98 and 9.24, 1H); 6.12 (bs, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Stage #1: at 20℃; for 0.75 h; Stage #2: at 90℃; for 18 h; |
Step 1: 3-Amino-4-nitrobenzonitrile (274) [0431] A suspension of bromoarene 2 (801mg; 3.7 MMOL) and zinc cyanide (570mg; 4. 85MMOL ; 1. 3eq. ) in degassed DIMETHYLFORMAMIDE (15 mL) was stirred at room temperature under nitrogen in the dark for 45 min and then treated with tetrakis (TRIPHENYLPHOSPHINE) PALLADIUM (O) (310mg, 1. 6MMOL). The mixture was stirred at 90°C for 18h; filtered through a celite pad, concentrated under reduced pressure and purified by flash chromatography on silica gel, eluent EtOAc-hexane (1 : 1) to afford the title compound 274 (380 mg, 63percent YIELD). H NMR: (400.2 MHz, CDCI3) 8 (ppm): 8.22 (d, J=8.6 Hz; 1H); 7.19 (d, J=1.8 Hz; 1H) ; 6.95 (dd, J=1.8, 8.6 Hz; 1H) ; 6.27 (bs; 2H). MS: CALC : 163.1 ; found: 164.1 (M+H) |
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