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CAS No. : | 4766-33-0 | MDL No. : | MFCD07369883 |
Formula : | C10H8BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VNPCNUAYDOLBDR-UHFFFAOYSA-N |
M.W : | 222.08 | Pubchem ID : | 19044893 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 56.05 |
TPSA : | 26.02 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.05 cm/s |
Log Po/w (iLOGP) : | 1.99 |
Log Po/w (XLOGP3) : | 2.26 |
Log Po/w (WLOGP) : | 3.19 |
Log Po/w (MLOGP) : | 3.24 |
Log Po/w (SILICOS-IT) : | 2.92 |
Consensus Log Po/w : | 2.72 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.26 |
Solubility : | 0.123 mg/ml ; 0.000553 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.44 |
Solubility : | 0.801 mg/ml ; 0.00361 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.57 |
Solubility : | 0.00594 mg/ml ; 0.0000267 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.24 |
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 |
---|---|---|
97% | With hydrogenchloride In 1,4-dioxane; ethanol; water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetic acid | 5-Amino-1-bromonaphthalene (B). To the solution of 5-nitro-1-bromonaphthalene (A) (2.5 g, 10 mmol) in EtOH/AcOH /Dioxane/H2O (2:2:2:1) (30 mL) was added Fe (5.6 g, 100 mmol) and 2 drops of 2 N HCl. The reaction mixture was stirred at 100° C. for 2 hrs. After evaporation of solvent, the residue was dissolved in 100 mL DCM and washed with 5percent NaHCO3 (3*30 mL) and dried over Na2SO4. After evaporation of solvent, the crude mixture was purified on a silica gel column, eluding with DCM/hexanes (1:1), to give compound B as a white powder (3.0 g, 97percent). mp 65-66° C.; 1H NMR (400 MHz, CDCl3) δ 7.79 (d, J=8.8 Hz, 1H), 7.76 (d, J=8.0, 1H), 7.71 (d, J=8.4 Hz, 1H), 7.39 (t, J=7.6 Hz, 1H), 7.28 (t, J=7.2 Hz, 1H), 6.83 (d, J=7.2 Hz, 1 H), 4.18 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 142.5, 133.0, 130.4, 128.0, 125.1, 125.0, 123.9, 121.0, 118.4, 110.9; ESI-MS (m/z) calcd. for C10H9BrN222.0 (M+H)+, found 222.1. Anal. Calcd for C10H8BrN: C, 54.08; H, 3.63; N, 6.31. Found: C, 53.81; H, 3.46; N, 6.11. |
84% | With iron; ammonium chloride In ethanol; water at 75℃; | To a suspension of 1-bromo-5-nitronaphthalene (2 g, 7.94 mmol) in EtOH (50 mL), a solution of NH4Cl (2.2 g, 41.1 mmol) in water (20 mL) was added, followed by iron powder (1.33 g, 23.82 mmol). The resulting mixture was stirred at 75° C. (bath temperature) for 1.5 h. Celite (3 g) was added, and the mixture was allowed to cool down to rt, diluted with CH2Cl2 (100 mL), filtered through a plug of Celite, washing with CH2Cl2 (150 mL). The filtrate was washed with brine and dried over Na2SO4. Upon evaporation of the filtrate, the crude material was redissolved in CH2Cl2 (20 mL), transferred on top of a 80 g SiO2 column, and ran with 20percent to 80percent EtOAc/hexane gradient. The fractions containing the product were evaporated to viscous light brown oil that quickly crystallized. Yield of 5-bromo-1-aminonaphthalene [West, R. W. J. Chem. Soc. 1925, 127, 494] 1.48 g (84percent). 5-Bromo-1-aminonaphthalene (1.37 g, 6.17 mmol) was dissolved in trimethyl phosphate (760 μL, 6.5 mmol) in a 50 mL round-bottom flask, equipped with an air condenser and a CaCl2 drying tube, the apparatus was flushed with nitrogen, and the mixture was heated at 200° C. (bath temperature) for 1.5 h. The flask was then allowed to cool below 100° C., 1 N NaOH (20 mL) was added, the resulting suspension was sonicated briefly and stirred at rt overnight. The mixture was diluted with brine, extracted with CH2Cl2 (3×50 mL), the combined extracts were dried over Na2SO4. The product was isolated by column chromatography (100 g of SiO2, gradient 10percent to 50percent CH2Cl2/hexane) to yield 1-bromo-5-(dimethylamino)naphthalene 28a [West, R. W. J. Chem. Soc. 1925, 127, 494] as a light-orange viscous oil (1.29 g, 84percent). 1H NMR (301 MHz, CDCl3): δ 8.26 (dt, J=8.6, 1.0 Hz, 1H), 7.95 (dt, J=8.6, 0.9 Hz, 1H), 7.78 (dt, J=7.4, 1.0 Hz, 1H), 7.51 (ddd, J=8.5, 7.5, 0.7 Hz, 1H), 7.32 (ddd, J=8.4, 7.3, 0.7 Hz, 1H), 7.14 (dd, J=7.6, 1.0 Hz, 1H), 2.90 (s, 6H) ppm. 13C NMR (76 MHz, CDCl3): δ 151.3, 133.4, 130.4, 130.1, 127.3, 125.4, 124.3, 123.3, 122.0, 115.0, 45.5. |
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