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CAS No. : | 142266-66-8 | MDL No. : | MFCD02932725 |
Formula : | C8H7Cl2NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QJUGBRJQIHDUNF-UHFFFAOYSA-N |
M.W : | 220.05 | Pubchem ID : | 612963 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 51.15 |
TPSA : | 50.19 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) : | -5.7 cm/s |
Log Po/w (iLOGP) : | 1.29 |
Log Po/w (XLOGP3) : | 2.73 |
Log Po/w (WLOGP) : | 2.7 |
Log Po/w (MLOGP) : | 0.71 |
Log Po/w (SILICOS-IT) : | 2.93 |
Consensus Log Po/w : | 2.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.2 |
Solubility : | 0.139 mg/ml ; 0.000631 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.44 |
Solubility : | 0.0802 mg/ml ; 0.000365 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.41 |
Solubility : | 0.085 mg/ml ; 0.000386 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.96 |
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 |
---|---|---|
96% | With sulfuric acid; sodium nitrite |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 94 percent / sulfuryl chloride / CCl4 / 6 h / Heating 2: 76 percent / POCl3 / Heating 3: 91 percent / aq. H2SO4 / Heating 4: 96 percent / H2SO4; aq. NaNO2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 76 percent / POCl3 / Heating 2: 91 percent / aq. H2SO4 / Heating 3: 96 percent / H2SO4; aq. NaNO2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide at 85 - 140℃; for 96h; Sealed tube; | 2.1 Step 1: 2-(azepan-1-yl)-5-chloro-4,6-dimethylnicotinic acid To a solution of 2,6-dichloro-4,6- dimethylnicotinic acid (0.50 g, 2.3 mmol) in DMF (5 mL) was added hexamethyleneimine (0.56 g, 5.7 mmol) and K2CO3 (1.0 g, 7.2 mmol). The mixture was heated at 85C for 3 days in a sealed tube, then additional hexamethyleneimine (0.50 g) and K2CO3 (1.0 g) were added. The mixture was heated at 140°C in a sealed tube for 24 hours, then cooled to rt and diluted with EtOAc. The organic layer was washed with 5% aqueous AcOH, water, brine, and then dried over MgSO4 and concentrated. The resulting residue was purified by silica gel chromatography (0-75% EtOAc/hexanes) to give the title compound. | |
With potassium carbonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 140℃; for 16h; Sealed tube; | 201.1 Step 1: 2-(azepan-l-yl)-5-chloro-4.6-dimethylnicotinic acid To a solution of 2,5-dichloro-4,6- dimethylnicotinic acid (0.50 g, 2.3 mmol) in DMF (5 mL) was added DIPEA (2.0 mL, 11 mmol), K2CO3 (2.0 g) and hexamethyleneimine (1.1 g, 11 mmol). The reaction vial was sealed and heated at l40°C for 16 hours. Then the reaction mixture was cooled to rt and diluted in EtOAc. The organic layer was washed with 5% AcOH in water, brine, dried over MgSOr. filtered and concentrated to give a residue that was purified via silica gel chromatography (0-75% (1662) EtO Ac/hexanes) to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; potassium carbonate / N,N-dimethyl-formamide / 16 h / 140 °C / Sealed tube 2: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 16 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: thionyl chloride / 1 h / 20 °C / Inert atmosphere 1.2: 20 °C 2.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 20 h / 25 - 220 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1 h / 20 °C / Inert atmosphere 1.2: 20 °C 2.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 20 h / 25 - 220 °C / Microwave irradiation 3.1: palladium [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO); caesium carbonate / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: thionyl chloride / 1 h / 20 °C / Inert atmosphere 1.2: 20 °C 2.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 20 h / 25 - 220 °C / Microwave irradiation 3.1: palladium [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO); caesium carbonate / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 1 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,5-dichloro-4,6-dimethylnicotinic acid With thionyl chloride at 20℃; for 1h; Inert atmosphere; Stage #2: methylamine In tetrahydrofuran; water at 20℃; | 214.1 Step 1 : 2.5-dichloro-N.4.6-trimethylnicotinamide A mixture of 2,5-dichloro-4,6- dimethylnicotinic acid (150 mg, 0.68 mmol) in SOCh (2.0 mL, 27 mmol) was stirred at room temperature for 1 hour under a nitrogen atmosphere. The mixture was evaporated under reduced pressure, and the resulting residue was dissolved in THF (2 mL). The solution was added dropwise into a solution of methanamine (2.0 mL, 0.68 mmol) in water at room temperature. The resultant mixture was purified by prep-TLC (petroleum ether: ethyl acetate 1 : 1) to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 96 h / 85 - 140 °C / Sealed tube 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 17 h / 50 °C |
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