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CAS No. : | 905710-66-9 | MDL No. : | MFCD11858305 |
Formula : | C8H6BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MKEWOMLQLUYQPK-UHFFFAOYSA-N |
M.W : | 212.04 | Pubchem ID : | 53407897 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 44.98 |
TPSA : | 44.02 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) : | -6.71 cm/s |
Log Po/w (iLOGP) : | 1.69 |
Log Po/w (XLOGP3) : | 1.24 |
Log Po/w (WLOGP) : | 1.66 |
Log Po/w (MLOGP) : | 1.59 |
Log Po/w (SILICOS-IT) : | 2.32 |
Consensus Log Po/w : | 1.7 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.27 |
Solubility : | 1.13 mg/ml ; 0.00533 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.76 |
Solubility : | 3.66 mg/ml ; 0.0173 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.17 |
Solubility : | 0.143 mg/ml ; 0.000673 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.7 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P280-P305+P351+P338-P311 | UN#: | 3439 |
Hazard Statements: | H302+H312-H315-H319-H331-H335 | Packing Group: | Ⅲ |
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 |
---|---|---|
44% | Stage #1: With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 3 h; Heating / reflux Stage #2: With sodium acetate In N,N-dimethyl-formamide at 80℃; |
To a solution of 17 (10.0 g, 49.5 mmol) in carbon tetrachloride (200 mL) were added N-bromosuccinimide (8.81 g, 49.5 mmol) and 2,2'-azobis(isobutyronitrile) (414 mg, 5 mol percent), and the mixture was refluxed for 3 h. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue were added dimethylformamide (150 mL) and sodium acetate (20.5 g, 250 mmol), and the mixture was stirred at 80° C. overnight. Water was added, and the mixture was extracted with ether. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue was added methanol (150 mL) and 1 mol/L sodium hydroxide (50 mL), and the mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated to about a third of volume under reduced pressure. Water and hydrochloric acid were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (3:1 hexane/ethyl acetate) followed by trituration with dichloromethane to give 2-bromo-5-cyanobenzyl alcohol (4.63 g, overall 44percent): 1H NMR (300 MHz, DMSO-d6) δ (ppm) 4.51 (d, J=5.9 hz, 2H), 5.67 (t, J=5.6 Hz, 1H), 7.67 (dd, J=8.2, 2.0 Hz, 1H), 7.80 (s, J=8.2 Hz, 1H), 7.83 (d, J=2.0 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | at 0℃; for 0.5 h; | To a solution of 4-bromo-3-formylbenzonitrile (1 g, 0.0047 mol) in methanol (10 mL) was added sodium borohydride(NaBH4; 0.18 g, 0.0047 mol) in portions, and the resulting mixture was stirred at 0 °C for 30 minutes (min). The reaction was quenched with saturated ammonium chloride (NH4C1) solution, and the mixture was concentrated under vacuum to remove the methanol. The resulting mass was dissolved in EtOAc, and the organic layer was washed with 0 and brine, dried over Na2S04 and concentrated. Trituration of the colorless solid which was obtained with n-hexane provided the title compound as white solid (0.9 g, 90percent): mp: 131-133° C; NMR (400 MHz, CDCb) δ 7.86 (dt, J = 1.8, 0.9 Hz, 1H), 7.67 (d, / = 8.1 Hz, 1H), 7.45 (ddt, / = 8.2, 2.0, 0.7 Hz, 1H), 4.79 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.51 g | With water; sodium hydroxide In methanol for 4 h; | Using a modification of the procedure by Baker and co-workers,refPreviewPlaceHolder12 1,1'-azobis(cyclohexanecarbonitrile) (0.343 g, 1.41 mmol) was added to a solution of 4-bromo-3-methylbenzonitrile (2.75 g, 14.1 mmol) and N-bromosuccinimide (2.75 g, 15.5 mmol) in α,α,α-trifluorotoluene (70 mL). The mixture was heated to reflux for 18 h. Upon cooling to room temperature, H2O (75 mL) was added and the mixture extracted with CH2Cl2 (3.x.50 mL). The combined organic phases were dried (MgSO4) and concentrated in vacuo. NaOAc (5.76 g, 70.0 mmol) was added to a solution of the residue in dimethyl formamide (45 mL) and the mixture was heated to 90 °C for 18 h. Upon cooling to room temperature, H2O (100 mL) was added and the mixture was extracted with EtOAc (3.x.75 mL). The combined organic phases were washed with brine (75 mL), dried (MgSO4) and concentrated in vacuo. Aqueous NaOH (2 M, 7.1 mL, 14.2 mmol) was added to a solution of the residue in MeOH (60 mL) and the mixture was stirred for 4 h. The solution was concentrated to 1/4 of its volume in vacuo and the mixture was extracted with EtOAc (3.x.50 mL). The combined organic phases were washed with brine (50 mL), dried (MgSO4) and concentrated in vacuo. The product was purified by column chromatography (20percent EtOAc/petroleum ether) to give the alcohol 27 (1.51 g, 51percent) as needles (hexane); mp=152-154 °C (hexane); δH (400 MHz, DMSO-d6): 7.83-7.86 (1H, m, ArH); 7.81 (1H, d, J 8.2 Hz, ArH), 7.68 (1H, dd, J 8.2, 2.1 Hz, ArH), 5.69 (1H, t, J 5.6 Hz, OH), 4.53 (2H, d, J 5.6 Hz, CH2); δC (101 MHz, DMSO-d6): 143.1, 133.4, 131.9, 131.0, 126.6, 118.3, 110.6, 62.1. The data were consistent with those reported by Baker and co-workers.refPreviewPlaceHolder12 S.J. Baker, Y.-K. Zhang, T. Akama, A. Lau, H. Zhou, V. Hernandez, W. Mao, M.R.K. Alley, V. Sanders and J.J. Plattner. J. Med. Chem., 49 (2006), pp. 4447-4450. Article | PDF (271 K) | View Record in Scopus| Cited By in Scopus (14) |
14 g | With water; sodium hydroxide In methanol at 20℃; for 2 h; | j0402j A mixture of 2-bromo-5-cyanobenzyl acetate (crude product, 13.5 g, 54.6 mmol, 1.0 eq), NaOH (2.55 g, 63.9 mmol, 1.2 eq) in methanol (150 ml) and water (50 mL) was stirred at room temperature for 2h. The water (150 ml) was added to mixture. Then the mixture was extracted with EA (3 x 6OmL) and the organic phase was washed by brine, dried with Na2SO4, concentrated in vacuum to give 4-bromo-3-(hydroxymethyl)benzonitrile (14.0 g) as brown solid. |
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