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CAS No. : | 50672-84-9 | MDL No. : | MFCD11101026 |
Formula : | C11H7BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SESASPRCAIMYLA-UHFFFAOYSA-N |
M.W : | 235.08 | Pubchem ID : | 4640413 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 57.04 |
TPSA : | 17.07 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) : | -5.37 cm/s |
Log Po/w (iLOGP) : | 2.11 |
Log Po/w (XLOGP3) : | 3.33 |
Log Po/w (WLOGP) : | 3.41 |
Log Po/w (MLOGP) : | 3.17 |
Log Po/w (SILICOS-IT) : | 3.79 |
Consensus Log Po/w : | 3.16 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.9 |
Solubility : | 0.0297 mg/ml ; 0.000126 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.37 |
Solubility : | 0.101 mg/ml ; 0.000431 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.88 |
Solubility : | 0.00309 mg/ml ; 0.0000132 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.06 |
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 |
---|---|---|
80.4% | With 1,6-Hexanediamine; acetic acid In water at 100℃; for 3 h; | A 3 L three-necked flask was charged with 318 g of 4-bromo-1-bromomethylnaphthalene (II)371.5 g of hexamethylenediamine,795g glacial acetic acid,795g water,100 ° C reflux reaction 3h,Point plate, the reaction is completed,Rapid dropwise addition of 636 g concentrated hydrochloric acid,Drop back 0.5h.Cooling to room temperature,Add 4L of water,Stir for 3 h.filter,Filter cake and then 2L water beating 2h,Filter,Filter cake washed twice with water,Drained,40 ° C drying.Adding 318 g of ethanol to recrystallize,Dried to give 200.4 g of 4-bromo-1-naphthaldehyde (III)Yield 80.4percent.Wherein the molar ratio of 4-bromo-1-bromomethylnaphthalene (II) to hexamethylenetetramine is 1: 2.5, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: With n-butyllithium In diethyl ether; hexane at 0℃; for 0.333333 h; Stage #2: at 0 - 20℃; for 1 h; |
To a 150 ml flask was added 1,4-dibromonaphthalene (2.0 g, 7.0 mmol) and anhydrous ether (50 ml). After cooling to 0 °C n-BuLi (3.1 ml of 2.5 M in hexanes, 7.7 mmol) was added dropwise and stirred for 20 minutes after which anhydrous DMF (1.62 ml, 21 mmol) was added. The reaction was then warmed to ambient temperature and after 1 h the reaction was quenched with water (10 ml), stirred for 10 minutes, and extracted with ether (3x). The ether layer was dried over anhydrous NA2S04, passed through a silica plug, and concentrated to afford 1.02 g (62percent) of product as a pure off- white solid : LH NMR (300 MHz, DMSO-D6) : 8 7.80-7. 85 (2H, m), 8.10 (1H, d, J = 7.7 Hz), 8.20 (1H, d, J = 7.7 Hz), 8. 32 (1H, m). 9.24 (1H, m), 10.42 (1H, s). Anal. for CIIH7BRO : Calc'd: C: 56.20 H: 3.00 Found: C: 56.13 H: 2.98 |
62% | Stage #1: With n-butyllithium In diethyl ether; hexane at 0℃; for 0.333333 h; Stage #2: at 20℃; for 1 h; |
Step 1: 4-Bromo-1 -naphthaldehyde (P20a)To a solution of 1,4-dibromonaphthalene (2.0 g, 7.0 mmol) in dry Et20 (50 mL) was added n5 BuLi (2.5M in hexanes, 3.1 mL, 7.7 mmol) at 0°C and the solution was stirred for 20 mm. ThenDMF (1.62 mL, 21 mmol) was added and the solution was warmed to rt and stirred at this temperature for 1 h, quenched with water and extracted with Et20 (3x). The combined organic layers were washed with brine, dried over Na2504, filtered, concentrated and purified by CC (PE/EA = 50/1) to give compound P20a (1.02 g, 62percent) as an off- white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With silica gel; pyridinium chlorochromate In dichloromethane at 20 - 25℃; for 2 h; | Step 2. 4-bromonaphthalene-1-carbaldehyde Into a 250-mL round-bottom flask, was placed dichloromethane (150 mL), (4-bromonaphthalen-1-yl)methanol (6.3 g, 26.57 mmol, 1.00 equiv), PCC (11.4 g, 183.72 mmol, 2.00 equiv) and 20 g Silicon dioxide. The resulting solution was stirred for 2 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and washed with ethyl acetate/petroleum ether (1/10-1/5). This resulted in 5.3 g (85percent) of 4-bromonaphthalene-1-carbaldehyde as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | at 80℃; for 4 h; | 1-Bromo-4-methylnaphthalene (1.06 g, 4.79 mmol) was dissolved in a 50percent acetic acid aqueous solution (100 ml). Diammonium cerium nitrate (7.61 g, 13.9 mmol) was added, and the mixture was stirred at 80°C for four hours. The reaction solution was cooled to room temperature and then water (300 mL) was added, followed by extraction with ethyl acetate (300 mL). The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate = 10/1) to give the target compound (173 mg, yield: 15percent) as a light yellow solid. 1H-NMR (CDCl3, 400MHz):δ ppm: 7.69-7.78 (2H, m), 7.82 (1H, d, J=7.8Hz), 7.99 (1H,d,J=7.8Hz),8.38(1H,d,J=8.4Hz),9.29(1H,d,J=8.4Hz),10.38(1H,s). MS (EI) m/z: 233.9679 (M+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With n-butyllithium In tetrahydrofuran; <i>N</i>-methyl-acetamide; water | Example 39 Preparation of 5,6-dichloro-2-[4-[(2,4-dioxothiazolidin-5-ylidene)methyl]naphth-1-yl]benzimidazole To a solution of 1,4-dibromonaphthalene (1.00 g, 3.50 mmol) in tetrahydrofuran (15 mL) were added n-butyllithium (1.6 mol/L; 3.1 mL) and dimethylformamide (0.54 mL, 7.0 mmol) sequentially at =78° C. under nitrogen atmosphere, and the mixture was stirred for 15 min. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was combined, washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (8:1 hexane/ethyl acetate) to afford 4-bromo-1-naphthalenecarboxaldehyde (458 mg, 56percent). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.6-7.8 (m, 2H), 7.78 (d, J=7.8 Hz, 1H), 7.94 (d, J=7.8 Hz, 1H), 8.34 (dd, J=8.2, 1.6 Hz, 1H), 9.25 (dd, J=8.2,1.6 Hz, 1H), 10.3 (s, 1H) |
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