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CAS No. : | 867333-29-7 | MDL No. : | MFCD03095323 |
Formula : | C6H5BClNO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KNFHCUNPMBSLRK-UHFFFAOYSA-N |
M.W : | 201.37 | Pubchem ID : | 24901770 |
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 : | 2.0 |
Molar Refractivity : | 50.1 |
TPSA : | 86.28 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) : | -6.62 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.28 |
Log Po/w (WLOGP) : | -0.07 |
Log Po/w (MLOGP) : | -0.22 |
Log Po/w (SILICOS-IT) : | -2.16 |
Consensus Log Po/w : | -0.23 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.1 |
Solubility : | 1.58 mg/ml ; 0.00786 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.69 |
Solubility : | 0.41 mg/ml ; 0.00204 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.29 |
Solubility : | 10.3 mg/ml ; 0.0513 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.24 |
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 |
---|---|---|
General procedure: A mixture of 7, (4.6 mmol), phenyl boronic acid (5.09 mmol), and Ba(OH)2·8H2O (9.2 mmol) in 15 mL of DME:H2O (5:1) was stirred under Ar for 15 min. To this, Pd(PPh3)4 (0.46 mmol) was added and the resulting solution was refluxed for overnight. The reaction was cooled and diluted with EtOAc (30 mL) and washed with NaHCO3 and brine. The resulting organic layer dried(Na2SO4) and evaporated to give a brown solid, which was purified by column chromatography using a gradient of 1:1 Hex:EtOAc yielded a white solid (90%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (2-chloro-5-nitrophenyl)boronic acid; 1-(2-bromophenyl)piperidine With barium hydroxide octahydrate In 1,2-dimethoxyethane; water for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water Reflux; Inert atmosphere; | Representative Suzuki Cross Coupling: 2-amino-5-nitro-biphenyl (8) General procedure: A mixture of 7, (4.6 mmol), phenyl boronic acid (5.09 mmol), and Ba(OH)2·8H2O (9.2 mmol) in 15 mL of DME:H2O (5:1) was stirred under Ar for 15 min. To this, Pd(PPh3)4 (0.46 mmol) was added and the resulting solution was refluxed for overnight. The reaction was cooled and diluted with EtOAc (30 mL) and washed with NaHCO3 and brine. The resulting organic layer dried(Na2SO4) and evaporated to give a brown solid, which was purified by column chromatography using a gradient of 1:1 Hex:EtOAc yielded a white solid (90%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; water; at 100℃; for 0.666667h;Inert atmosphere; Microwave irradiation; | Example 10 [0166] <strong>[6141-13-5]2-Chloroquinazoline</strong> (150 mg, 0.91 mmol), 2-chloro-5- nitrophenylboronic acid (239 mg, 1 .18 mmol), Pd2dba3 (21 mg, 0.023 mmol), PCy3 (26 mg, 0.093 mmol) were loaded into a microwave vial equipped with a stirbar. The vial was capped with a Teflon septum and purged with argon (by needle) for 5 min. Then 2.0 mL 1 ,4-dioxane and 1 .0 mL of 1 .27 M K3P04 (aq.) were added via syringe and the solution was further degassed with argon for 5 min. The vial was then subjected to microwave irradiation for 40 mins at 100 C. The reaction mixture was then concentrated, adsorbed onto silica gel, and purified via silica chromatography (eluent: ethyl acetate in hexanes) to afford the product as a white crystalline solid (38 mg, 15%) along with recovered 2- <strong>[6141-13-5]chloroquinazoline</strong> (52 mg, 35%). 1H-NMR (400 MHz, d6-DMSO): delta 9.82 (s, 1 H), 8.68 (d, J = 2.8 Hz, 1 H), 8.37 (dd, J = 2.9, 8.8 Hz, 2H), 8.29 (d, J = 8.1 Hz, 1 H), 8.14-8.13 (m, 1 H), 7.96 (d, J = 8.8 Hz, 1 H), 7.88 (ddd, J = 3.4, 4.6, 8.1 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With palladium diacetate; potassium carbonate; In water; isopropyl alcohol; at 25℃; for 3h; | 2-nitro-phenylboronic acid (0.201 g, 1 mmol), potassium carbonate (0.138 g, 1 mmol, 1 eq), palladium acetate (0.0112 g, 0.05mmol, 5 mol%), isopropanol (5ml) water (5ml) in a mixed solvent 2-bromopyridine (0.174 g, 1.1 mmol, 1.1 eq) was added dropwise under stirring with stirring, and the reaction was carried out at 25 C for 3 hours. The residue was treated with ethyl acetate (V: v = 1: 1) to give the productintermediate 2- (2-chloro-propionic acid) in the presence of a mixture of petroleum ether and ethyl acetate (v: v = 1: 1)5-nitrophenyl) pyridine (2) 0.219 g, yield 96%. |
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