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CAS No. : | 426219-35-4 | MDL No. : | MFCD14708203 |
Formula : | C12H10BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HPUCFMPIKISIIO-UHFFFAOYSA-N |
M.W : | 264.12 | Pubchem ID : | 21879628 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.08 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 64.64 |
TPSA : | 29.1 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.68 cm/s |
Log Po/w (iLOGP) : | 2.34 |
Log Po/w (XLOGP3) : | 3.14 |
Log Po/w (WLOGP) : | 2.96 |
Log Po/w (MLOGP) : | 3.18 |
Log Po/w (SILICOS-IT) : | 3.18 |
Consensus Log Po/w : | 2.96 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.82 |
Solubility : | 0.0402 mg/ml ; 0.000152 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.42 |
Solubility : | 0.1 mg/ml ; 0.00038 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.32 |
Solubility : | 0.00128 mg/ml ; 0.00000484 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.06 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
89% | Stage #1: With thionyl chloride; N,N-dimethyl-formamide In toluene at 45 - 50℃; for 1 h; Stage #2: With triethylamine In methanol; toluene at 10 - 25℃; for 1 h; |
Reference Example 76-Bromo-2-naphthoic acid (10.1 g, 40.1 mmol) and N,N- dimethylformamide (4.75 g, 65.0 mmol) were added to toluene (80 mL) . To the reaction mixture was added dropwise thionyl chloride (5.7 g, 48.2 mmol) at 45 to 50°C, and the mixture was stirred for 1 hr, and allowed to cool to room temperature. The reaction mixture was added dropwise at 10 to 25°C to a solution prepared by adding triethylamine (11.4 g, 112.4 mmol) and 40percent methylamine methanol solution (8.1 g, 104.4 mmol) to toluene (80 rnL) , and the mixture was stirred at room temperature for 1 hr.. To the reaction mixture was added dropwise water (50 mL) , and the mixture was stirred at room temperature. The crystals were collected by filtration, and washed with a mixed solvent (25 mL) of methanol/water (2:8) to give wet crystals. The total amount of the wet crystals was added to N,N- dimethylacetamide (70 mL) , and dissolved with heating to 60°C. The reaction mixture was allowed to cool to room temperature, and water (140 mL) was added dropwise thereto. The crystals were collected by filtration, and washed with water (80 mL) to give wet crystals. The total amount of the wet crystals was suspended in ethyl acetate -(25 mL) with stirring at roomtemperature. The crystals were collected by filtration, and washed with ethyl acetate (5 mL) . The obtained wet crystals were dried under reduced pressure to give 6-bromo-N-methyl-2- naphthamide (9.4 g, 35.6 mmol). yield 89percent.3/4 NMR (500 MHz, DMSO-d6) δ 2.84 (d, J = 4.4 Hz, 3H) , 7.71 (dd, J = 8.8, 2.2 Hz, 1H) , 7.93 - 8.03 (m, 3H) , 8.28 (d, J = 1.9 Hz, 1H), 8.44 (s, 1H) , 8.62 (d, J = 4.1 Hz, 1H) ; HRMS (ESI) m/z Calcd for a Ci2HuNOBr [M+H]+: 264.0024, Found: 264.0019; Anal. Calcd for a Ci2Hi0NOBr: C, 54.57; H, 3.82; N, 5.30; Br, 30.25. Found: C, 54.56; H, 3.70; N, 5.34; Br, 30.23. |
82% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 18 h; Inert atmosphere | Under an argon atmosphere, to a cooled (0 °C) solution of 8 (60.26 g, 240 mmol), EDCI*HCl (55.21 g, 288 mmol), HOBt*H2O (44.1 g, 288 mmol) and N,N-diisopropylethylamine ((i-Pr)2NEt) (37.23 g, 288 mmol) in anhydrous N,N-dimethylformamide (DMF) (960 mL) was added dropwise to a solution of MeNH2 (2 M solution in THF; 192 mL, 384 mmol) and the whole was stirred at room temperature for 18 h. After dilution with water, the precipitate was filtered off, washed with H2O and i-Pr2O and dried under the reduced pressure to give 9a (60.6 g, 82percent) as a colorless powder. 1H NMR (CDCl3 + CD3OD) δ: 3.04 (3H, s), 7.60 (1H, dd, J = 1.8 Hz, 8.6 Hz), 7.78 (2H, d, J = 8.6 Hz), 7.85 (1H, dd, J = 1.8 Hz, 8.6 Hz), 8.03 (1H, d, J = 1.8 Hz), 8.25 (1H, s). IR (KBr): 3274, 1638, 1622, 1559, 1495, 1408, 1316, 1159 cm-1. Anal. Calcd for C12H10NOBr.0.1H2O: C, 54.20; H, 3.87; N, 5.27; Br, 30.25. Found: C, 54.03; H, 3.72; N, 5.24. |
80% | Stage #1: With thionyl chloride In DMF (N,N-dimethyl-formamide); ethyl acetate at 30 - 65℃; for 0.5 h; Stage #2: With triethylamine In methanol; DMF (N,N-dimethyl-formamide); water; ethyl acetate at 25℃; for 3 h; |
4 Liters of ethyl acetate and 25 ML of DMF were added to 500 g (1.99 mol) of 6-bromo-2-naphthoic acid. 188 ML (2.61 mol, 1.3eq) of thionyl chloride was added dropwise at 30°C or lower.. The mixture was stirred at 65°C for 30 minutes.. After cooled to 25°C, a mixture of 408 ML (3.93 mol, 2eq) of a 40percent solution of methylamine in methanol and 558 ML (4.01 mol, 2eq) of triethylamine was added dropwise at 25°C or lower.. The mixture was stirred at 25°C for 3 hours. 2.5 Liters of water was added dropwise at 25°C or lower.. Crystals were filtered, and washed successively with 1.25 liters of a mixed solution of methanol/water=1/4.. Vacuum drying (50°C) to a constant weight afforded 422 g of 6-bromo-N-methyl-2-naphthamide (yield 80percent).1H NMR (CDCl3+CD3OD): δ 3.04 (3H, s), 7.60 (1H, dd, J=8.6, 1.8 Hz), 7.78 (2H, d, J=8.6 Hz), 7.85 (1H, dd, J=8.6, 1.8 Hz), 8.03 (1H, d, J=1.8 Hz), 8.25 (1H, s). |
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