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CAS No. : | 872422-15-6 | MDL No. : | MFCD12405622 |
Formula : | C10H8BrFO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UPADMCJEKQAEKT-UHFFFAOYSA-N |
M.W : | 259.07 | Pubchem ID : | 66662682 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 53.03 |
TPSA : | 37.3 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) : | -6.09 cm/s |
Log Po/w (iLOGP) : | 2.06 |
Log Po/w (XLOGP3) : | 2.52 |
Log Po/w (WLOGP) : | 3.06 |
Log Po/w (MLOGP) : | 3.0 |
Log Po/w (SILICOS-IT) : | 3.31 |
Consensus Log Po/w : | 2.79 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.22 |
Solubility : | 0.156 mg/ml ; 0.000604 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.95 |
Solubility : | 0.291 mg/ml ; 0.00112 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.72 |
Solubility : | 0.0489 mg/ml ; 0.000189 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.73 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
70% | Stage #1: With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water at 50℃; for 10 h; Stage #2: With sodium hydroxide In water; ethylene glycol at 100℃; |
Step 1. 1-(4-Bromo-2-fluorophenyl)cyclopropanecarboxylic acid Sodium hydroxide, 50percent aqueous solution (5.71 mL, 0.149 mol), was added to a mixture of (4-bromo-2-fluorophenyl)acetonitrile (3.16 g, 0.0145 mol), benzyltriethylammonium chloride (0.26 g, 0.0011 mol), and 1-bromo-2-chloro-ethane (2.51 mL, 0.0302 mol) at 50° C. for 10 h. The mixture was poured into ice-water (50 mL) and was extracted with ethyl ether (2*50 mL). The combined organic phase was washed with brine (30 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give 2.88 g of brown solid. 1H-NMR confirmed that desired nitrile intermediate was isolated. To the resulting residue was added 50percent NaOH aqueous solution (3.8 mL) and ethylene glycol (20 mL) and the solution was heated to 100° C. and stirred overnight. The reaction mixture was poured into 50 mL of water and washed with ether (2*50 mL). The aqueous layer was cooled with an ice bath and then acidified by the slow addition of 6 N HCl. to pH=2. The product was extracted with EtOAc (2*100 mL), dried over MgSO4 and concentrated to give 1.634 g. (70percent) of the desired product. 1H NMR confirmed that the desired product was isolated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With water; potassium hydroxide In ethanol for 7 h; Reflux | A solution of the compound (24.6 g, 102 mmol) obtained in Example 14-2) and potassium hydroxide (46 g, 820 mmol) in ethanol (200 ml) and water (40 ml) was heated to reflux for 7 h. The reaction mixture was cooled to room temperature, and then 5 N hydrochloric acid was added until the reaction mixture was rendered acidic. The deposited solid was collected by filtration, washed with water, and then dried to obtain the title compound (28.7 g, quant.) as a colorless solid. 1H-NMR (400 Hz, CDCl3) δ: 1.23 (2H, m), 1.72 (2H, m), 7.10-7.15 (1H, m), 7.22-7.25 (2H, m) |
10.87 g | at 100℃; | In a 1 L round-bottomed flask, l-(4-bromo-2-fluorophenyl)cyclopropanecarbonitrile (1 1.2 g, 46.7 mmol) and LiOH (58 g, 1.38 mol) were combined with water (230 mL) to give a yellow suspension. The mixture was heated in an oil bath at 100 °C overnight. The mixture was diluted to 1 L with water and ice and extracted with ethyl ether (3 x 300 mL). There was some white insoluble material between phases that was not included in aqueous layer. The aqueous layer was acidified with concentrated HC1 (ca. 1 10 mL) slowly with addition of ice. A very fine precipitate formed and the milky solution was not filtered but extracted with DCM (4 x 250 ml). The organic layers were combined, dried over MgS04, filtered, and concentrated yielding l-(4-bromo-2-fluorophenyl)cyclopropanecarboxylic acid (10.87 g, 89.9percent yield) as a yellow solid. LC/MS calcd. for Ci0H8BrFO2 (m/e) 258/260, obsd. 259/261 (M+H, ES+). |
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