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CAS No. : | 16588-34-4 | MDL No. : | MFCD00007078 |
Formula : | C7H4ClNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HETBKLHJEWXWBM-UHFFFAOYSA-N |
M.W : | 185.57 | Pubchem ID : | 85505 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 45.66 |
TPSA : | 62.89 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) : | -6.07 cm/s |
Log Po/w (iLOGP) : | 0.89 |
Log Po/w (XLOGP3) : | 1.92 |
Log Po/w (WLOGP) : | 2.06 |
Log Po/w (MLOGP) : | 0.86 |
Log Po/w (SILICOS-IT) : | 0.48 |
Consensus Log Po/w : | 1.24 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.44 |
Solubility : | 0.677 mg/ml ; 0.00365 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.86 |
Solubility : | 0.254 mg/ml ; 0.00137 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.34 |
Solubility : | 0.84 mg/ml ; 0.00453 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.6 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H317-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 |
---|---|---|
97% | for 2 h; Cooling | To the mixture of nitrosonitric acid (55 mL) and sulfuric acid (55 mL) was added 4-chlorobenzaldehyde (70 g, 0.5 mol) in batches at 5 °C and stirred for 2 h. Then the mixture was poured slowly to ice water (1 L) while stirring constantly. The resulting precipitate was filtered and recrystallized from ethanol/water to give product 13 (90 g, 97percent) as white acicular crystal. Mp: 62-63 °C |
94% | at 0 - 20℃; for 0.5 h; Inert atmosphere | General procedure: 10 mmol of the desired p-substituted benzaldehyde was dissolved in 5 mL of conc. sulfuric acid, and cooled to 0 °C, and then 1.2 equiv. of nitric acid was dissolved in 1 mL of conc. sulfuric acid, and then slowly added to the reaction mixture. The reaction was allowed to warmgradually to room temperature and stirred for 30 min at room temperature. It was then poured into 50 mL of ice-cold water. The produced precipitate was filtered and washed with cold water. The product was purified on reverse phase column chromatography with gradient increase of methanol in water containing 0.1percent of formic acid as eluent. |
75% | at 150℃; for 0.025 h; Microwave irradiation | General procedure: The microwave (MW) reactor used was of CEM make, which was equipped with temperature, pressure, and MW power control units. An oven-dried MW vial was charged with a mixture containing aromatic compound, V2O5 (9 mg, 0.005 mmol) and 69percent HNO3 (0.063 mL, 1 mmol) and silica gel slurry, and irradiated in a MW (power input 140 W) at 150 °C for few minutes. After completion of the reaction, as as certained by TLC, the reaction mixture was treated with sodium bicarbonate; the organic layer was diluted with dichloromethane (DCM) and separated from aqueous layer. The crude product mixture was purified with ethyl acetate DCM mixture. The purity was checked with TLC. The products were identified by characteristic spectroscopic data. |
70% | at 0 - 40℃; for 1 h; | General procedure: The nitration of aldehydes was carried out in a three-neckedflask of 50 ml with magnetic stirrer. H2SO4 25 ml (0.47 M)were cooled to 0 °C, 3.1 ml (0.070 M) of HNO3 were added,and then the aldehyde (0.06 M) was slowly added. Thereaction was carried out at a temperature of 0–5 °C. Then,the mixture was heated at 40 °C for 1 h. The reaction waspoured into ice water and filtered under a vacuum; thenitrobenzaldehydes were purified by recrystallization. Thescheme of reaction is showed in Fig. 1 (Furniss et al. 1989).The spectrums of 1H NMR of nitrobenzaldehydes wereobtained in CDCl3 and TMS as reference. 4-chloro-3-nitrobenzaldehyde: Yellow solid; mp 60–62 °C; yield: 70percent; 1H NMR (600MHz, CDCl3), 7.89(d, J = 8.16, 1H Ar–H), 8.25 (d, J = 8.16, 1H, Ar–H), 8.98(t, J = 8.16, 1H, Ar–H), 10.01 (s, 1H, –CHO). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.5% | With potassium fluoride In thiophene; water | EXAMPLE 5 18.6 g (0.1 mol) of 4-chloro-3-nitrobenzaldehyde and 8.7 g (0.15 mol) of potassium fluoride in 100 ml of sulpholane are stirred for 1 hour at 180° C. The mixture is stirred with 300 ml of water and the aldehyde is extracted with methylene chloride. After the customary working-up, 17.1 g of 92percent strength 4-fluoro-3-nitrobenzaldehyde are obtained. Yield: 92.5percent of the theoretical yield. |
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