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CAS No. : | 90484-53-0 | MDL No. : | MFCD16036864 |
Formula : | C9H7BrO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OILDTPUIIUEPFL-UHFFFAOYSA-N |
M.W : | 243.05 | Pubchem ID : | 53419620 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 50.81 |
TPSA : | 43.37 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.0 cm/s |
Log Po/w (iLOGP) : | 2.03 |
Log Po/w (XLOGP3) : | 2.51 |
Log Po/w (WLOGP) : | 2.05 |
Log Po/w (MLOGP) : | 2.0 |
Log Po/w (SILICOS-IT) : | 2.54 |
Consensus Log Po/w : | 2.23 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.07 |
Solubility : | 0.206 mg/ml ; 0.000848 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.07 |
Solubility : | 0.208 mg/ml ; 0.000858 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.28 |
Solubility : | 0.127 mg/ml ; 0.000524 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.64 |
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% | With silver nitrate In water; acetone at 20℃; for 1 h; Darkness | To a solution of methyl 3-bromo-4-(dibromomethyl)benzoate (32.0 g, 65.3 mmol) in acetone (400 ml) was added silver nitrate (33.3 g, 196 mmol) and water (100 mL). The suspension was stirred at ambient temperature in the dark for 1 h. The silver salts were removed by filtration and thefiltrate diluted with EtOAc, washed with brine, saturated sodium bicarbonate and water. The organiclayer was dried (Na2504), concentrated and purified on silica (EtOAc/hexanes, 0-20percent) to obtainmethyl 3-bromo-4-formylbenzoate (12.9 g, 52.0 mmol, 80percent yield) as a white solid. 1H NMR(400MHz, DMSO-d6) 6 ppm 10.26 (s, 1H), 8.23 (s, 1H), 8.08 (d, J=8.1 Hz, 1H), 7.97 (d, J=8.0 Hz, 1H),3.91 (s, 3H); LC/MS (m/z) ES : 243 (M÷1) |
58% | Stage #1: With water; silver nitrate In ethanol for 1.5 h; Darkness; Reflux Stage #2: With hydrogenchloride In water; acetonitrile at 70℃; for 2 h; Reflux |
To a solution of methyl 3-bromo-4-(dibromometyl)benzoate (60)[14] (42.5 g, 110 mmol) in ethanol (500 mL) was added a solution of silver nitrate (112.0 g, 659 mmol) in water (150 mL). The reaction mixture was protected from light and refluxed for 90 min. After cooling to room temperature, a concentrated hydrochloric acid solution (37percent, w/w) was added until pH ≤ 1. The formed precipitate was then filtered and the filtrate was concentrated to remove ethanol. After extraction with dichloromethane (3 x 150 mL), the combined organic layers were dried over magnesium sulfate, filtered and evaporated under reduced pressure to give a mixture of the corresponding diethyl acetal and aldehyde. This mixture was diluted with an acetonitrile/water solution (3/1 v/v, 420 mL) in the presence of a catalytic amount of concentrated hydrochloric acid solution (37percent, w/w) and then refluxed at 70 °C for 2 h. After cooling to room temperature, sodium carbonate was added portionwise until the formation of two phases. After decantation the aqueous layer was extracted with dichloromethane (3 x 200 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated under reduced pressure to give methyl 3-bromo-4-formylbenzoate (61) (15.5 g, 64 mmol) as a yellow solid. Yield 58percent; Rf (Al2O3, cyclohexane/ethyl acetate, 9/1, v/v) 0.60; mp 79-81°C (litt.[15]: 334-335 °C); IR (KBr) ν 1281, 1379, 1437, 1697, 1736, 2958, 3070 cm-1; 1H NMR (200 MHz, CDCl3) δ 3.95 (s, 3H, CH3), 7.94 (d, 1H, J = 8.0 Hz, H-5), 8.05 (dd, 1H, J = 8.0, 1.4 Hz (H-6), 8.29 (d, 1H, J = 1.4 Hz (H-2), 10.39 (s, 1H, CHO); 13C NMR (50 MHz, CDCl3) δ 52.9 (CH3), 126.7 (C-3), 128.8 (C-6), 129.8 (C-5), 135.1 (C-2), 136.1 (C-4 or C-1), 136.3 (C-4 or C-1), 164.9 (CO2), 191.3 (CHO). |
43% | With silver nitrate In water; acetonitrile for 0.333333 h; Reflux | Method 1 : To a solution of methyl 3-bromo-4-(dibromomethyl)benzoate (intermediate compound 21 ) (056 mmol, 220 mg) in acetonitrile (1 ml_) was added a solution of AgN03 (1 .68 mmol, 285 mg) in water (0.5 mL), and the mixture was heated for 20 min under reflux. After the solution was allowed to cool, AgBr was filtered off and washed with DCM, the combined filtrate was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by flash chromatography on silica gel using an elution of 4percent ethylacetate in hexanes afforded methyl 3-bromo-4- formylbenzoate 23 (59 mg. Yield: 43percent). |
43% | With silver nitrate In water; acetonitrile for 0.333333 h; Reflux | full text is not avalable from article |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With trimethylamine-N-oxide In dichloromethane; dimethyl sulfoxide at 0 - 28℃; for 8 h; | Method 2: To a solution of methyl 3-bromo-4-(bromomethyl)benzoate (intermediate compound 22) (1 .43 mmol, 442 mg) in dichloromethane at 05C was added a DMSO solution (3.2 mL) of trimethylamine oxide (5.72 mmol, 430 mg). The reaction mixture was warmed at 285C for 8 h. To this mixture was added Na2C03 solution, and the organic layer was extracted with DCM, and washed with brine, dried over MgS04 and concentrated to give methyl 3-bromo-4- formylbenzoate 23 (173 mg. Yield:49percent). 1 H NMR (400 MHz, CDCI3) δ 10.41 (1 H, s), 8.32 (1 H, s), 8.07 (1 H, d, J = 8Hz), 7.96 (1 H, d, J = 8Hz), 3.97 (3H, s). LC-MS: tR = 3.25 [M+H]+ = not ion (method 3). |
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