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CAS No. : | 2674-34-2 | MDL No. : | MFCD00025694 |
Formula : | C8H8Br2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CHCLRVOURKGRSW-UHFFFAOYSA-N |
M.W : | 295.96 | Pubchem ID : | 231240 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 54.83 |
TPSA : | 18.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.8 cm/s |
Log Po/w (iLOGP) : | 2.82 |
Log Po/w (XLOGP3) : | 3.25 |
Log Po/w (WLOGP) : | 3.23 |
Log Po/w (MLOGP) : | 2.93 |
Log Po/w (SILICOS-IT) : | 3.17 |
Consensus Log Po/w : | 3.08 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.96 |
Solubility : | 0.0324 mg/ml ; 0.00011 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.31 |
Solubility : | 0.144 mg/ml ; 0.000488 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.35 |
Solubility : | 0.0133 mg/ml ; 0.0000449 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.81 |
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 |
---|---|---|
30% | Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 2 h; Stage #2: at -78 - 20℃; for 15 h; |
1,4-Dibromo-2,5-dimethoxybenzene (2.0 g, 6.76 mmol) was added dissolved in THF 35 mL, it was added dropwise a 1.6 M BuLi slowly at -78 . After stirring the reaction solution for 2 hours at -78 , it was added dropwise to DMF (2.8 mL, 33.7 mmol). The reaction solution is stirred at room temperature for 15 hours (20 ). 2 N HCl in a 20 mL reaction mixture was stirred slowly dropping off. The resulting solid was then filtered under reduced pressure, dried to obtain a 2,5-dimethoxyterephthalaldehyde 267 mg (30percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With bromine In chloroform at 0℃; for 3 h; | Example 2: Preparation of 2,5-dibromo-1 ,4-dimethoxybenzene (2); [00103] In a one liter round-bottom flask, a solution of bromine (35.2 g, 220 mmol) in chloroform (50 ml) was added dropwise to a solution of 1 ,4- dimethoxybenzene (13.8 g, 100 mmol) in chloroform (400 ml) under 00C. After stirring for 3 hours, 100 ml of saturated Na2CO3 solution was added. The organic layer was washed with water, brine, and dried over sodium sulfate. The solvent was removed on a rotary evaporator and the residue was performed recrystallization from ethanol to afford pure 2,5-dibromo-1 ,4- dimethoxybenzene (25.8 g, 85percent). 1HNMR (CDCI3) 57.128 (s, 2 H), 3.873 (s, 6 H). |
83.6% | at 20℃; for 4 h; Sonication | In a 250 ml reaction flask, 20.0 g (0.145 mol, 1.0 eq) of hydroquinone dimethyl ether and 55 ml of glacial acetic acid were added and dissolved by ultrasonic; A solution of 15 ml of Br2 (0.290 mol, 2.0 eq) and 15 ml of glacial acetic acid was added dropwise at room temperature. After 1.5 hours, the mixture was stirred at room temperature for 2.5 h. Placed in the upper refrigerator to 10 below the temperature (not to acetic acid curing) filter; and petroleum ether washing filter cake to give a white solid, vacuum drying and then weight 35.6g, the yield of 83.6percent. |
68% | for 16 h; Cooling with ice | 1,4-dimethoxybenzene (1.66 g, 12.0 mmol) was dissolved in 25 mL glacial acetic acid and cooled in an ice bath. Bromine (1.3 mL, 25 mmol) was carefully added. The cooling bath was removed and the reaction was stirred for 16 h and then poured over ice. The reaction mixture was extracted 3 x with 100 mL of CHCl3. The combined organics were dried over MgSO4, filtered, and the solvents were removed under vacuum. The product was isolated via recrystallization in absolute ethanol to yield white needles (2.40 g, 68percent), mp 140-142 C (lit.5 mp 144-145 C). 1H NMR (CDCl3): δ 7.12 (s, 2H), 3.86 (s, 6H). The 1H NMR matches the known spectrum.5 |
63% | With bromine In acetic acid at 20℃; for 2 h; | To a solution of 1,4- dimethoxybenzene Q-8 (7.5 g, 53.57 mmol) in acetic acid (25 mL) was added a solution of bromine (17.4 g, 108.9 mmol) in acetic acid (5 mL) at room temperature. After stirring for 2h, the solution was cooled to 10 0C. The resulting fine precipitate was filtered, washed with water (20 mL), and dried under vacuum to obtain compound Q-9 (1Og, 63percent) as a white solid. TLC Rf = 0.5 (petroleum ether - EtOAc, 9.9:0.1); 1H NMR (CDCl3) δ 7.10 (s, 2H), 3.84 (s, 6H). |
61% | With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 20 - 80℃; for 6 h; | General procedure: To a stirred solution of starting compound (0.5–1.2 mmol) in DMF–H2O (95:5, v/v, 8–12 mL) mixture was added NBS (4.0–4.2 mmol) at room temperature. The contents were stirred at room temperature about 10 min and then heated for appropriate duration mentioned in Table 2. Progress of the reaction in every case was monitored by TLC analysis. After completion of the reaction, the reaction mixture was cooled to room temperature and quenched with aqueous NaHCO3 (20percent, 20–30 mL) solution. The insoluble precipitate was isolated by filtration and dried in vacuo. It was further purified by either recrystallization with ethyl acetate/n-hexane mixture or short pad silica gel column chromatography led to pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With boron tribromide In dichloromethane for 24 h; Reflux | In a 100 ml single-necked flask, 7.1 g (24.2 mmol, 1.0 eq) of 1,4-dibromo-2,5-dimethoxybenzene and 30 ml of dichloromethane were added. After the addition of the addition of BBr3 4.6ml (49.6mmol, 2.05eq), reflux reaction 24h. The methylene chloride was distilled off, and 50 ml of water was added with stirring. The filter cake was washed with water and washed with water. And dried in vacuo to give 5.08 g of a white solid in 79percent yield. |
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