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CAS No. : | 99-60-5 | MDL No. : | MFCD00007209 |
Formula : | C7H4ClNO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QAYNSPOKTRVZRC-UHFFFAOYSA-N |
M.W : | 201.56 | Pubchem ID : | 7448 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.23 |
TPSA : | 83.12 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.09 cm/s |
Log Po/w (iLOGP) : | 0.86 |
Log Po/w (XLOGP3) : | 2.03 |
Log Po/w (WLOGP) : | 1.95 |
Log Po/w (MLOGP) : | 1.11 |
Log Po/w (SILICOS-IT) : | -0.26 |
Consensus Log Po/w : | 1.14 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.58 |
Solubility : | 0.532 mg/ml ; 0.00264 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.4 |
Solubility : | 0.0796 mg/ml ; 0.000395 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.77 |
Solubility : | 3.4 mg/ml ; 0.0169 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.68 |
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 |
---|---|---|
98% | Stage #1: With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1 h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 16 h; |
λ/,iV'-Carbonyldiimidazole (19.91 g, 122 mmol) is added batchwise to 2-chloro-4- nitrobenzoic acid (25 g, 90 percent purity, 111 mmol) in anhydrous THF (420 mL) at RT and stirred for 1 h. At 15 - 20 0C, NaBH (13.09 g, 346 mmol) in water (85 mL) is added dropwise thereto and the mixture is stirred for 16 h at RT. The reaction mixture is adjusted to pH 1 with 6 N HCl and exhaustively extracted with EtOAc. The combined organic <n="26"/>phases are washed with 15 percent potassium carbonate solution (2 x 150 mL) and saturated saline solution (150 mL), dried, filtered and evaporated down. Yield: 20.60 g (98 percent |
97% | Stage #1: With borane In tetrahydrofuran at 20℃; for 16 h; Stage #2: With water; potassium carbonate In tetrahydrofuran |
Starting with acid 52: a solution of 2-chloro-4-nitrobenzoic acid (15.95 g, 79 mmol, 1.0 equiv.) in THF (200 mL) was cooled to 0 0C. BH3 (118.7 mL, 118.7 mmol, 1 M solution in THF, 1.5 equiv.) was added dropwise. Reaction mixture was allowed to warm to room temperature and stirred for 16 h. A sat'd solution OfK2CO3 in water was added dropwise untill gas evolution stopped. After precipitation of a white solid, the r.m. was filtered and washed with EtOAc. Filtrate and washings were combined and concentrated in vacuo. The product was redissolved in EtOAc, washed with IN HCl (2x), sat'd NaHCO3 and brine and dried on Na2SO4. After filtration and concentration in vacuo, compound 53 was obtained as a yellowish solid in 97percent yield (14.45 g)- |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | at 20℃; for 2.5 h; | First, NaBH4 (1 mmol) was used as a reducing agent forthe conversion of Ag (+ 1) to Ag (0) in methanol at roomtemperature for 2 h. After that, the Ag/MMT was filtered andused as a catalyst. Then, in a typical procedure, a mixtureof 4-nitrophenol (0.1 mmol), KOH (0.15 mmol), isopropylalcohol (3 mL), and Ag/MMT catalyst (50 mg) 1.01 wtpercentwas stirred at room temperature for an appropriate time(Scheme 2). After the completion of the reaction (monitoredby GC), the catalyst was separated by filtration. The ensuingproduct was extracted with ethyl acetate and repeatedlywashed with water (3–4 times) to remove KOH. The resultingsolvent was evaporated to dryness in vacuum. |
24% | With iron; ammonium chloride In ethanol; water for 2 h; Reflux | Step 5a. 4-Amino-2-chlorobenzoic acid (compound 3002) A mixture of 2-chloro-4-nitrobenzoic acid (5.0 g, 24.8 mmol), iron powder (8.0 g, 142.9 mmol) and NH4Cl (7.6 g, 142.9 mmol) in EtOH/water (50/50 mL) was heated at reflux for 2 h. The hot mixture was filtered through Celite and washed with ethyl acetate. The mixture was separated and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate. The crude product was purified by column chromatography (hexanes/ethyl acetate: 5/1, 3/1, 1/1) to afford compound 3002 as a white solid (1.0 g, 24percent yield). 1H NMR (400 MHz, DMSO-d6): δ 6.04 (s, 2H), 6.49 (dd, J=8.4 Hz, 2.0 Hz, 1H), 6.61 (d, J=2.0 Hz, 1H), 6.63 (d, J=8.8 Hz, 1H), 12.21 (br, 1H). |
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