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CAS No. : | 6627-51-6 | MDL No. : | MFCD00045161 |
Formula : | C7H6BrCl | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SDTULEXOSNNGAW-UHFFFAOYSA-N |
M.W : | 205.48 | Pubchem ID : | 138789 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 44.12 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.71 cm/s |
Log Po/w (iLOGP) : | 2.43 |
Log Po/w (XLOGP3) : | 4.01 |
Log Po/w (WLOGP) : | 3.41 |
Log Po/w (MLOGP) : | 3.95 |
Log Po/w (SILICOS-IT) : | 3.62 |
Consensus Log Po/w : | 3.49 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.13 |
Solubility : | 0.0151 mg/ml ; 0.0000735 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.71 |
Solubility : | 0.0398 mg/ml ; 0.000194 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.26 |
Solubility : | 0.0113 mg/ml ; 0.0000552 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.28 |
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 |
---|---|---|
94% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -88℃; for 1.5 h; Inert atmosphere; Schlenk technique; Glovebox Stage #2: at 20℃; Inert atmosphere; Schlenk technique; Glovebox |
165 ml (413 mmol) of 2.5 M nBuLi in hexanes was added dropwise over 1 h to a solution of 82.2 g (400 mmol) of 4-bromo-3-chlorotoluene in 400 ml of THF cooled to -88 °C. The resulting mixture was stirred for 30 min at this temperature, and then 44.0 g (602 mmol) of DMF was added dropwise by vigorous stirring for 10 min. The reaction mixture was stirred overnight at room temperature, and then 100 ml of water and 400 ml of 3 N HC1 were added at 0 °C. The organic layer was separated, the aqueous layer was extracted with 2 x 125 ml of dichloromethane. The combined organic extract was dried over K2CO3 and then passed through a short layer of silica gel 60 (40-63 μιη). The silica gel layer was additionally washed by 50 ml of dichloromethane. The combined organic eluate was evaporated to dryness to give a slightly orange liquid which was then distilled under vacuum to give 58.0 g (94percent) of the title product (b.p. 99-102 °C/11 mm Hg,) as a colorless liquid crystallized overnight at room temperature. |
94% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -88℃; for 1.5 h; Stage #2: at 20℃; |
165 ml ( 413 mmol) of 2.5 M nBuLi in hexanes was added dropwise over 1 hto a solution of 82.2 g ( 400 mmol) of 3-chloro-4-bromo-toluene in 400 ml of THFcooled to -88°C. The resulting mixture was stirred for 30 min at this temperature,and then 44.0 g (602 mmol) ofDMF was added dropwise over 10 min by vigorousstirring. The reaction mixture was stirred overnight at room temperature, then cooled to ooc in an ice bath and then 100 ml of water and 400 ml of 3N HCl were added.The organic layer was separated and the aqueous layer was extracted with 2x 125 mlof dichloromethane. The combined organic extract was dried over K2C03 and thenpassed through a short layer of silica gel 60 ( 40-63 )liD). The silica gel layer wasadditionally washed with 50 ml of dichloromethane. The combined organic elute was evaporated to dryness to give a slightly orange liquid which was then distilled invacuum to give 58.0 g (94percent) ofthe title product (b.p. 99-102°C/11 mm Hg,) as acolorless liquid that crystallized overnight at room temperature. Anal. calc. for C8H7Cl0: C, 62.15; H, 4.56. Found: C, 62.24; H, 4.45.1H NMR (CDCh): b 10.4 (s, 1H, CHO), 7.80 (d, J= 7.8 Hz, 1H, 6-H), 7.25(s, 1H, 3-H), 7.17 (d, J = 7.8 Hz, 1H, 5-H), 2.40 (s, 3H, 4-Me). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | at -20℃; for 0.0833333 h; | Con. HNO3 (15 mL) was added to the solution of 1-bromo-2-chloro-4-methylbenzene (20 g, 100 mmol) in con.H2S04 (65 mL) at -20 °C slowly. The reaction was stirred for 5 mins andthen poured into ice-water (500 g). Then, the mixture was filtered and the solid was washed by water and dried to give the crude product as a yellow solid. (23 g, 95percent yield).D533 1H NMR (400 MHz, CDCI3) 58.27 (s, 1H), 7.46 (s, IH), 2.56 (s, 3H). |
62% | With sulfuric acid; nitric acid In water at -20 - 25℃; | In a 50-mL round-bottomed flask was placed l-bromo-2-chloro-4-methylbenzene (2 g, 9.7 mmol) and concentrated H2SO4 (6.5 mL). The mixture was cooled to -20 0C and HNO3 (1.5mL) was added slowly over 5 min. To the reaction mixture was added ice water (15 g) after the addition OfHNO3. After allowing to warm to RT, the reaction mixture was extracted with EtOAc (2 X 10 mL). After drying (Na2SO4) the combined organic layers were concentrated in vacuo and the crude product was purified by ISCO MPLC (petroleum ether) to afford the title compound (1.3 g) in 62percent yield. 1H NMR (CDCl3) δ 2.56 (s, 3 H), 7.44 (s, 1 H), 8.28 (s, 1 H). |
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