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CAS No. : | 84102-69-2 | MDL No. : | MFCD02667598 |
Formula : | C11H9BrO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XLJWAHXKBCDQNP-UHFFFAOYSA-N |
M.W : | 269.09 | Pubchem ID : | 735184 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.18 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 60.0 |
TPSA : | 39.44 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) : | -5.29 cm/s |
Log Po/w (iLOGP) : | 2.98 |
Log Po/w (XLOGP3) : | 3.74 |
Log Po/w (WLOGP) : | 3.37 |
Log Po/w (MLOGP) : | 2.36 |
Log Po/w (SILICOS-IT) : | 3.24 |
Consensus Log Po/w : | 3.14 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.11 |
Solubility : | 0.0209 mg/ml ; 0.0000775 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.26 |
Solubility : | 0.0148 mg/ml ; 0.0000549 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.62 |
Solubility : | 0.00644 mg/ml ; 0.0000239 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.57 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H312-H315-H319-H332-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 |
---|---|---|
60% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In DMF (N,N-dimethyl-formamide) at 140℃; for 2 h; | To a solution of 5-bromo-2-hydroxy-benzaldehyde (50.9 g, 253. 2 mmol) and ethyl bromoacetate (46.5 g, 278.5 mmol) in acetone (300 mL) is added K2CO3 (45.4 g, 329 mmol). The suspension is stirred for 16 h at RT, and the solid is filtered. The filtrate is concentrated to a residue and dissolved in DMF (100 mL), DBU (38.5 g, 253 mmol) is added and the solution is heated to 140 °C for 2 h. The reaction mixture is cooled down and poured into water (500 mL) and extracted with EtOAc (300 mL, 100 mL). The organic layer is dried over Na2S04, concentrated, purified on column chromatography (10percent EtOAc/Hex), to give the title compound as an oil (41.6 g, 60percent) H-NMR (ppm, CDC13) 8 : 7.81 (1 H, d, J=1. 8 Hz), 7.54 (1 H, dd, J=1.8, 8.8 Hz), 7.47 (1 H, d, J=9. 2 Hz), 7.44 (1 H, s), 4.47 (2 H, q, J=7. 0 Hz), 1. 44 (3 H, t, J=7. 0 Hz). |
27% | Stage #1: With sodium ethanolate In ethanolHeating / reflux Stage #2: With sulfuric acid In ethanol for 2 h; Heating / reflux |
EXAMPLE 2 Preparation of ethyl 5-bromo-1-benzofuran-2-carboxylate; [0081] EMI299.0[0082] The compound was prepared according to a literature procedure.(Yoo et al., Bioorg. Med. Chem. 5:445, 1997). To ethyl (4-bromo-2-formylphenoxy)acetate (Example 1, 14.3 g, 49.7 mmol) was added, under Ar, 115 mL absolute EtOH. To this mixture was added 5.28 g (77.7 mmol) sodium ethoxide and the reaction allowed to reflux overnight. Sulfuric acid (conc., 2 mL) was then added, and the reaction allowed to reflux an additional 2 hours. The mixture was then cooled to rt, 50 mL water was added and the pH adjusted to neutrality with 1 N NaOH. The mixture was then extracted with 150 mL EtOAc, and the combined organic phase was washed with brine (2*150 mL), dried over Na2SO4, and filtered. The solvent was removed in vacuo. Purification by Biotage(R) separation using 5percent EtOAc/hexanes provided 3.62 g (27percent) of the desired compound. <1>H-NMR (CDCl3, [delta]): 1.43 (t, 3H), 4.45 (q, 2H), 7.46-7.57 (m, 3H), 7.82 (s, 1H); LRMS (GC/MS/ED) 268 [M]<+>. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 5 h; | Add to a 250 mL two-necked flask5-bromo-2-hydroxybenzaldehyde (15 g, 74.63 mmol)Ethyl bromoacetate (18.7g, 111.9mmol),Potassium carbonate (31 g, 223.9 mmol)And anhydrous DMF (80 mL),The reaction mixture was heated to 130 ° C for 5 hours to complete the reaction.Filtration, the filtrate is concentrated under reduced pressure,The residue was dissolved in ethyl acetate (100 mL)Washed with saturated brine (50 mL x 3)Dried over anhydrous sodium sulfate.Filtration, evaporation of the solvent under reduced pressure,The crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 20, V / V)A pale yellow solid of 16.6 g,Yield 83percent. |
59.7% | With caesium carbonate In N,N-dimethyl-formamide at 20 - 120℃; for 2.5 h; | 5-bromosalicylaldehyde (0504-89) (5 g, 25 mmol, 1.0 eq.)And cesium carbonate (8.2 g, 25 mmol, 1.0 eq.)Mix in 80 ml DMF,Ethyl bromoacetate (8.3 g, 50 mmol, 2.0 eq.) was added dropwise.After the addition was completed, the reaction was performed at room temperature for half an hour.Warm up to 120°C for two hoursAfter the liquid detection reactionAll, cool to room temperature, pour it into ice water and stir for half an hour. Filter, filter cake washed with water,Drying gave a yellow powdered solid product, ethyl 5-bromobenzofuran-2-carboxylate (4 g, 59.7percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With sodium hexamethyldisilazane In tetrahydrofuran at -40℃; for 10 h; | Compound 1 (1.0 mmol) and dibromoacetylene (1.2 mmol) were dissolved in THF at -40 °C.NaHMDS (2.0 mmol) was added, and the reaction was kept at -40 ° C for 10 hours (the compound 1 disappeared completely by TLC).After quenching the reaction with saturated ammonium chloride, the THF was evaporated under reduced pressure.After washing with saturated sodium chloride, the combined organic phases were dried over anhydrous sodium sulfateCompound 2 (226 mg, yield 84.0percent,The HPLC purity was 97.8percent and 1H NMR was consistent with known reports). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sulfuric acid In ethanol | 5C Ethyl 5-bromo-2-benzofurancarboxylate A solution of 5-bromo-2-benzofurancarboxylic acid (5.01 g, 20.8 mmol) in absolute ethanol (150 ml) was added with concentrated sulfuric acid (15 ml) and the mixture was refluxed under stirring for 2 h. After this time, the volatiles were evaporated off under reduced pressure and the resulting residue was neutralized with a sodium bicarbonate saturated solution and extracted with ethyl ether (4*100 ml). The mixture was dried and the solvent was evaporated off under reduced pressure, to obtain 5.19 g of the title compound as a white solid with melting point 58-60° C. (93percent yield). 1 H N.M.R. (300 MHz, CDCl3) δ ppm: 1.34 (t, 3H); 4.35 (q, 2H); 7.39 (m, 3H); 7.71 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With potassium carbonate In butanone for 72 h; Heating / reflux | A solution of 5-bromo-salicylaldehyde (5.0 g, 25 mmol) and bromo diethylmalonate (8.9 g, 37 mmol) in methyl ethyl ketone (50 ml) is treated with potassium carbonate (6.8 g, 50 mmol) and heated to reflux. The reaction is stirred over 3 days at reflux. The reaction is then concentrated to a crude solid that is purified by silica gel column chromatography (9:1 hexane / EtOAc) to afford 5.2 g (78 percent) of the desired product. 1H NMR (CDCl3) 7.81 (d, 1H), 7.26-7.55 (m, 3H), 4.44 (q, 2H), 1.42 (t, 3H) |
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