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CAS No. : | 7499-66-3 | MDL No. : | MFCD01026466 |
Formula : | C10H8BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UBLKHAWYJFEPDX-UHFFFAOYSA-N |
M.W : | 222.08 | Pubchem ID : | 348404 |
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) : | -5.55 cm/s |
Log Po/w (iLOGP) : | 2.01 |
Log Po/w (XLOGP3) : | 2.97 |
Log Po/w (WLOGP) : | 3.19 |
Log Po/w (MLOGP) : | 3.24 |
Log Po/w (SILICOS-IT) : | 2.92 |
Consensus Log Po/w : | 2.87 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.7 |
Solubility : | 0.0438 mg/ml ; 0.000197 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.18 |
Solubility : | 0.147 mg/ml ; 0.000661 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 : | 1.16 |
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 |
---|---|---|
100% | Stage #1: With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide at 20℃; for 3 h; Stage #2: With water In N,N-dimethyl-formamide at 100℃; for 1 h; |
Part B. Preparation of 6-bromonaphthalen-2 -amine.; [00748] A solution of the product Part A (5.07g, 20.19mmol) and triethylamine (4.22mL, 3.07g, 30.3mmol) in dry DMF (155mL) was treated with the diphenylphosphoroyl azide (6.55mL, 8.34g, 30.3mmol) followed by stirring at room temperature for 3h. The solution was then treated with water (2OmL) followed by warming at 1000C for Ih. The solution was cooled and the flask fitted with a short- path distillation head and the DMF removed by distillation under high vacuum. The solid residue was dissolved in EtOAc and washed with saturated sodium bicarbonate solution. Filtered through celite and the filtrate was washed with water (3x) and then with brine. Dried over Na2SC^, filtered and concentrated under vacuum to give the title compound as a beige solid (4.48g, 100 percent). |
100% | Stage #1: With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide at 20℃; for 3 h; Stage #2: With water In N,N-dimethyl-formamide at 100℃; for 1 h; |
[00490] Part B. Preparation of 6-bromonaphthalen-2-amine.; [00491] A solution of the product Part A (5.07g, 20.19mmol) and triethylamine (4.22mL, 3.07g, 30.3mmol) in dry DMF (155mL) was treated with the diphenylphosphoroyl azide (6.55mL, 8.34g, 30.3mmol) followed by stirring at room temperature for 3h. The solution was then treated with water (2OmL) followed by warming at 1000C for Ih. The solution was cooled and the flask fitted with a short- path distillation head and the DMF removed by distillation under high vacuum. The solid residue was dissolved in EtOAc and washed with saturated sodium bicarbonate solution. Filtered through celite and the filtrate was washed with water (3x) and then with brine. Dried over Na2SO4, filtered and concentrated under vacuum to give the title compound as a beige solid (4.48g, 100 percent). |
100% | Stage #1: With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide at 20℃; for 3 h; Stage #2: With water In N,N-dimethyl-formamide at 100℃; for 1 h; |
Part 1. Preparation of 6-bromonaphthalen-2 -amine.[00328| A solution of the product Part H (5.07 g, 20.19 mmol) and triethylamine (4.22 mL, 3.07 g,30.3 mmol) in dry N.N-dimethylformamide (155mL) was treated with the diphenylphosphoroyl azide(6.55 mL, 8.34 g, 30.3 mmol) followed by stirring at room temperature for 3 hours. The solution was then treated with water (20 mL) followed by warming at 100 0C for 1 hour. The solution was cooled and the flask fitted with a short-path distillation head and the NN-dimethylformamide was removed by distillation under high vacuum. The solid residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic layer was filtered through diatomaceous earth, and the filtrate was washed with water (3*) and then with brine. The organic layer was dried overNa2SO4, filtered and concentrated under vacuum to give the title compound as a beige solid (4.48 g,100 percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | at 150℃; for 48 h; | 6-bromonaphthalen-2-amine (15)6-Bromonaphthalen-2-ol (1.5 g, 6.7 mmol) was heated with ammonium hydroxide (10ml) and ammonium sulfite (3.5 g, 26 mmol) in a seal tube at 150 0C for 48 h. After cooling to room temperature, ethyl acetate was added and organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and evaporated to obtain crude product 15 (1.4 g, Y; 94 percent), which was pure enough and can be used directly for next step without further purification. 1H NMR (CDCl3): δ 7.84 (IH, br), 7.56 (IH, d, J= 9.6 Hz), 7.43 (2H, m), 6.95 (2H, m), 3.87 (2H, b). Leigh C. Anderson and Donald G. Thomas: Quinoidation of Triaryl Compounds - Hydroxynaphthyldiphenylcarbinols J. Am. Chem. Soc; 65; 1943; 239, 241. |
33% | With ammonium bisulfite; ammonia In water at 190℃; for 24 h; | Preparation of 6-Bromonaphthalen-2-amine (9) 6-Bromo-2-naphthol (2.0 g, 9 mmol), ammonium sulfite (10.4 g, 90 mmol) and 10 mL of ammonia solution were sealed in a tube. The reaction mixture was heated at 190° C. for 24 hrs and allowed to cool to room temperature, the reaction mixture was extracted with EtOAc. HCl (10percent) was added to the organic layer to give a precipitate. After filtration, the solid was dissolved in 10percent of Na2CO3 and extracted with EtOAc, the organic layer was dried over Na2SO4. The solvent was removed under reduced pressure to give the product as yellow solid (0.67 g, 33percent). MS [M++43]=265, LC-MS: tR=20.14 min. |
21% | With ammonium hydroxide; ammonium sulfite monohydrate In water at 120℃; for 17 h; | General procedure: Ammonium hydroxide aqueous solution ( 841mg, 27.8 mmol, 2 equiv.) was added to a freshly prepared aqueous solution of ammonium sulfite monohydrate (3.2 g, 27.8 mmol, 2 equiv.) in a 35 ml high pressure reaction vessel. Appropriate 2-naphthol analog (1a or 1b) (13.9 mmol, 1 equiv.) was added, and the mixture was stirred for 17 h at 120 °C. The reaction mixture was filtered and the precipitate was washed with cold 5percent aq. NaOH and then dissolved in DCM. The organic layer was again washed with 5percent aq. NaOH (3×30 mL) and dried over anh. sodium sulfate to afford 2-naphthylamines after the removal of solvent in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With hydrogenchloride In methanol at 20℃; for 4 h; | General Procedure VII-SA flask was charged with VII-IB (5.5 g, 17.1 mmol) and HCl/MeOH (4M, 170 mL) was stirred at room temperature for 4 hrs. After the completion of reaction, the mixture was concentrated to afford 6-bromonaphthalen-2-amine (VII-Vd) (2.5 g, yield 66percent). |
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