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CAS No. : | 131001-86-0 | MDL No. : | MFCD00144762 |
Formula : | C9H9BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QAOFGUXVDAZKBW-UHFFFAOYSA-N |
M.W : | 229.07 | Pubchem ID : | 10823279 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 50.39 |
TPSA : | 26.3 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) : | -5.69 cm/s |
Log Po/w (iLOGP) : | 2.39 |
Log Po/w (XLOGP3) : | 2.83 |
Log Po/w (WLOGP) : | 2.54 |
Log Po/w (MLOGP) : | 2.97 |
Log Po/w (SILICOS-IT) : | 2.84 |
Consensus Log Po/w : | 2.71 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.28 |
Solubility : | 0.12 mg/ml ; 0.000523 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.04 |
Solubility : | 0.209 mg/ml ; 0.000912 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.72 |
Solubility : | 0.0436 mg/ml ; 0.000191 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.6 |
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 |
---|---|---|
43% | With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; Inert atmosphere | Intermediate 8: 2-(Bromomethyl)-6-methyl-benzonitrile Step 1 : Methyl 2-cyano-3-methylbenzoate A solution of methyl 2-bromo-3-methyl-benzoate (5 g, 21.8 mmol), Zn(CN)2 (10.26 g, 87.3 mmol) and Pd(PPh3)4 (1.51 g, 1.3 mmol) in DMF (60 mL) was stirred at 80 °C under N2 overnight. The solvent was removed in vacuo. The residue was dissolved in DCM (100 mL) and washed with H20 (50 mL). The organic layer was dried over Na2S04, filtered and concentrated to give the crude product, which was purified by column (eluting with 10percent EtOAc in PE) to give methyl 2-cyano-3-methyl-benzoate (1.6 g, yield 43percent) as a white solid: 1H NMR (400 MHz, CD3OD) δ 7.97-7.95 (m, 1H), 7.68-7.62 (m, 2H), 3.96 (s, 3H), 2.60 (s, 3H); ES-LCMS m/z: 176.1 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.5% | for 3 h; Reflux | General procedure: To a solution of 21 (150 g, 697.5 mmol) in MeOH (1350 mL) was added SOCl2 (165.0 g, 2.0 equiv) dropwise at 5-10 °C. The mixture was refluxed for 3 h and then MeOH was removed. EA was added to extract the product and the EA layer was washed by water, Na2CO3/H2O, separated and concentrated to give the methyl ester as orange oil (158.7 g, yield 99.5percent). HPLC purity is 96percent. To a 2 L 3-necked flask were added the methyl ester obtained (158.7 g), CCl4 (1440 mL), NBS (128.7 g, 1.05 equiv) and BPO (8.4 g, 0.05 equiv). The mixture was heated to 80-85 °C, stirred for 5 h, cooled to rt and filtrated. After removal of solvent, EA was added into the residue, washed with 2 N Na2S2O3, concentrated to give 67 as orange oil (229.5 g, yield 100percent). CaCO3 (166.3 g, 2.4 equiv) was added into the solution of 67 (229.5 g) in a mixed solvent of THF (1380 mL) and H2O (1380 mL). The mixture was stirred at 100 °C for 5.0 h, cooled to rt, filtered, extracted with EA, concentrated to give the crude 68 as orange oil (199.0 g) that was purified by a short silica gel column to give 68 with 100percent HPLC purity as yellow solid (89.4 g, yield 52.6percent). Silica gel (152.5 g) was added into the solution of 68 (152.5 g) in DCM (2280 mL). PCC (201.0 g, 1.5 equiv) was added in portions at 0-10 °C and the mixture was stirred for 3 h. The solvent was removed to give the crude 69 (163.0 g) that was purified by a short silica gel column to give 69 as black oil (142.7 g, yield 94.4percent). Pyridinium p-toluenesulfonate (PPTS, 14.7 g, 0.1 equiv) was added into the solution of 69 (142.7 g) in toluene (2.8 L) and ethylene glycol (72.9 g, 2.0 equiv). The mixture was stirred at 130 °C for 5.0 h, cooled to 40 °C and concentrated. The residue was purified by a short silica gel column to give 70 as yellow oil (160.1 g, yield 95.0percent). To a solution of 70 (5 g, 17.48 mmol) in dry THF (90 mL) was added CH3MgI (25 mL, 4 mol/L) dropwise at -10 °C. The mixture was stirred overnight warming to rt, quenched by NaHCO3 and extracted with EA. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (PE/EA = 4:1) to give 71 (4.2 g, yield 84percent) as a solid. 1H NMR (300 MHz, CDCl3): δ 7.72 (d, 1H), 7.53 (d, 1H), 7.33 (t, 1H), 6.23 (s, 1H), 4.18-4.05 (m, 4H), 2.81 (s, 1H), 1.78 (s, 6H). MS:m/z = 287 and 289 (M+1, ESI+). To a solution of 71 (4.2 g, 14.634 mmol) in dry THF (70 mL) was added n-BuLi (12.3 mL, 2.5 M, 2.1 equiv) dropwise at -78 °C under N2 and stirred for 30 min. Trimethyl borate (3.2 mL, 2 equiv) was added at -78 °C. The mixture was stirred overnight warming to rt, quenched with water and acidified with 1 NHCl to pH 2-3. The reaction mixture was stirred for 1 h and extracted with EA. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (PE/EA = 3:1) to give 72 (176 mg, yield 6.8percent) as a solid. 1HNMR(300 MHz, DMSO-d6): δ 10.36 (s, 1H), 9.08 (s, 1H), 7.78-7.86 (m, 2H), 7.68 (t, 1H), 1.51 (s, 6H) ppm. MS: m/z = 191 (M+H). A mixture of 72 (176 mg, 0.9263 mmol), 2,2-dimethyl-1,3-dioxane-4,6- dione (147 mg, 1.019 mmol, 1.1 equiv) in HCOOH/TEA (1.9 mL, v/v = 5:2) was heated to 110 °C for 12 h. The mixture was cooled to rt and powered into ice water. The mixed solution was acidified with 1 N HCl to pH 1 and extracted with EA. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by preparative TLC (PE/EA = 2:1) to give 20 (23.5 mg, yield 10.8percent) as a white solid. |
89% | Heating / reflux | 25.0 g (11.6 mmol ; 1.0 eq) of 2-bromo-3-methylbenzoic acid and 22.0 g (11.6 MMOL) of para-toluenesulfonic acid are dissolved in 580 ml of methanol and refluxed overnight. After cooling, the reaction medium is concentrated under reduced pressure. The residue is dissolved in ether and then washed twice with saturated aqueous sodium hydrogen carbonate solution and then with water and with solution saline. The organic phase is then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The expected product is obtained in the form of a pale yellow oil (23.6 g; 89percent) and is then used without further purification. |
83% | for 20 h; Reflux | A mixture of 2-bromo-3-methylbenzoic acid (5 g, 23.2 mmol) and sulfuric acid (0.5 mL) in anhydrous methanol (100 mL) was refluxed for 20 hours then concentrated in vacuo. The residue was dissolved in dichloromethane (50 mL), washed with a saturated solution of sodium hydrogenacarbonate (30 mL), dried over sodium sulfate and concentrated in vacuo to provide methyl 2-bromo-3-methylbenzoate (28a) (4.43 g, 19.3 mmol, 83percent).1 H NMR (400 MHz, CDCI3) 2.46 (s, 3H), 3.93 (s, 3H), 7.24 (t, J = 8.0 Hz, 1 H), 7.34 (dd, J = 1 .0 Hz, J= 8.0 Hz, 1 H), 7.46 (dd, J = 1 .0 Hz, J= 8.0 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With hydrogenchloride In methanolReflux | A solution of 2-bromo-3-methylbenzoic acid (3.7g, 17.2mmol, 1equiv), 2,2-dimethoxypropane (9g, 86.3mmol, 5equiv), and hydrochloric acid (12M, 2.9mL, 34.4mmol, 2equiv) in methanol (44mL) was refluxed overnight. After cooling, the solvent was removed in vacuo. The residue was dissolved in Et2O and washed with water. Organic extract was dried over Na2SO4, filtered, and concentrated in vacuo. Crude product was purified by flash column chromatography over silica gel (heptane/Et2O 97:3) to give the methyl 2-bromo-3-methylbenzoate (3.3g, 96percent) as a colorless oil. Rf=0.37 (Pentane/Et2O 95:5). 1H NMR (400MHz, CDCl3) δ (ppm)=7.47–7.45 (m, 1H, H-6), 7.34 (ddd, 3J=7.6Hz, 4J=2Hz, 5J=0.8Hz, 1H, H-4), 7.24 (br t, 3J=7.6Hz, 1H, H-5), 3.93 (s, 3H, H-9), 2.46 (s, 3H, H-7). 13C NMR (100MHz, CDCl3) δ (ppm)=167.9 (C-8), 139.9 (C-3), 134.2 (C-1), 133.2 (C-4), 128.0 (C-6), 127.0 (C-5), 123.2 (C-2), 52.6 (C-9), 24.0 (C-7). IR (CDCl3) ν (cm−1)=2951, 1729, 1433, 1293, 1193, 1142, 1029, 973, 874, 789, 752, 701, 573. MS (GC EI, 70eV) 227.79 ([M+·], 38percent), 196.79 (100percent), 168.81 (23percent), 88.92 (43percent). |
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