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CAS No. : | 87565-98-8 | MDL No. : | MFCD11226177 |
Formula : | C7H9ClN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 188.61 | Pubchem ID : | - |
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 : | 3.0 |
Molar Refractivity : | 47.57 |
TPSA : | 75.35 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) : | -7.49 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | -0.06 |
Log Po/w (WLOGP) : | 1.28 |
Log Po/w (MLOGP) : | 0.17 |
Log Po/w (SILICOS-IT) : | -0.28 |
Consensus Log Po/w : | 0.22 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.21 |
Solubility : | 11.6 mg/ml ; 0.0617 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.07 |
Solubility : | 16.0 mg/ml ; 0.0849 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.45 |
Solubility : | 6.74 mg/ml ; 0.0357 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.47 |
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 |
---|---|---|
With sodium nitrite; In hydrogenchloride; | Example A To a solution (200 mL) of m-amino benzoic acid (200 g, 1.46 mol) in concentrated HCl was added an aqueous solution (250 mL) of NaNO2 (102 g, 1.46 mol) at 0 C. The reaction mixture was stirred for 1 h and a solution of SnCl2.2H2O (662 g, 2.92 mol) in concentrated HCl (2 L) was then added at 0 C., and the reaction stirred for an additional 2h at RT. The precipitate was filtered and washed with ethanol and ether to yield 3-hydrazino-benzoic acid hydrochloride as a white solid. | |
With sodium nitrite; In hydrogenchloride; | Example AA To a solution of m-aminobenzoic acid (200.0 g, 1.46 mmol) in concentrated HCl (200 mL) was added an aqueous solution (250 mL) of NaNO2 (102 g, 1.46 mmol) at 0 C. and the reaction mixture was stirred for 1 h. A solution of SnCl2.2H2O (662 g, 2.92 mmol) in concentrated HCl (2000 mL) was then added at 0 C. The reaction solution was stirred for an additional 2 h at RT. The precipitate was filtered and washed with ethanol and ether to give 3-hydrazino-benzoic acid hydrochloride as a white solid, which was used for the next reaction without further purification. 1H NMR (DMSO-d6): 10.85 (s, 3H), 8.46 (s, 1H), 7.53 (s, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.37 (m, J=7.6 Hz, 1H), 7.21 (d, J=7.6 Hz, 1H). | |
With sodium nitrite; In hydrogenchloride; | EXAMPLE A To a solution (200 mL) of m-amino benzoic acid (200 g, 1.46 mol) in concentrated HCl was added an aqueous solution (250 mL) of NaNO2 (102 g, 1.46 mol) at 0 C. The reaction mixture was stirred for 1 h and a solution of SnCl2.2H2O (662 g, 2.92 mol) in concentrated HCl (2 L) was then added at 0 C., and the reaction stirred for an additional 2 h at RT. The precipitate was filtered and washed with ethanol and ether to yield 3-hydrazino-benzoic acid hydrochloride as a white solid. |
With sodium nitrite; In hydrogenchloride; | Example A To a solution (200 mL) of m-amino benzoic acid (200 g, 1.46 mol) in concentrated HCl was added an aqueous solution (250 mL) of NaNO2 (102 g, 1.46 mol) at 0 C. The reaction mixture was stirred for 1 h and a solution of SnCl2.2H2O (662 g, 2.92 mol) in concentrated HCl (2 L) was then added at 0 C., and the reaction stirred for an additional 2 h at RT. The precipitate was filtered and washed with ethanol and ether to yield 3-hydrazino-benzoic acid hydrochloride as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | In ethanol; | A mixture of <strong>[87565-98-8]3-hydrazino-benzoic acid hydrochloride</strong> (200 g, 1.06 mol) and 4,4-dimethyl-3-oxo-pentanenitrile (146 g, 1.167 mol) in ethanol (2 L) was heated to reflux overnight. The reaction solution was evaporated under reduced pressure. The residue was purified by column chromatography to give 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid ethyl ester (116 g, 40%) as a white solid together with 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid (93 g, 36%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of m-aminobenzoic acid (200 g, 1.46 mmol) in cone. HCl (200 mL) was added an aqueous solution (250 mL) of NaNO2 (102 g, 1.46 mmol) at 0 C and the reaction mixture was stirred for Ih. A solution of SnCl2-2H2O (662 g, 2.92 mmol) in cone. HCl (2 L) was then added at 0 C. The reaction solution was stirred for an additional 2h at RT. The precipitate was filtered and washed with EtOH and ether to give 3-hydrazinobenzoic acid hydrochloride as a white solid, which was used for the next reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40%; 36% | In ethanol;Heating / reflux; | A mixture of <strong>[87565-98-8]3-hydrazinobenzoic acid hydrochloride</strong> (200 g, 1.06 mol) and 4,4- dimethyl-3-oxopentanenitrile (146 g, 1.167 mol) in EtOH (2 L) was heated at reflux overnight. The reaction solution was evaporated under reduced pressure. The residue was purified by column chromatography to give 3-(5-amino-3-t-butyl-pyrazol-1-yl)-benzoic acid ethyl ester (116 g, 40%) as a white solid together with 3-(5-amino-3-t-butyl-pyrazol-1- yl)benzoic acid (93 g, 36%). 3-(5-amino-3-t-butyl-pyrazol-1-yl)benzoic acid and ethyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sodium acetate; In ethanol; for 10h;Reflux; | General procedure: A mixture of the appropriate hydrazone 2a-e (0.035 mol), anhydrous sodium acetate (0.5 g) and the proper phenyl hydrazine hydrochloride (0.035 mol) in absolute ethanol (25 mL) was heated under reflux for 10 h. The separated solid was filtered off, dried and crystallized from aqueous ethanol to afford 5a-i in excellent yield (68 - 85%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine; In ethanol; at 20℃; for 1h; | To a solution of methyl 3-(dimethylamino)-2-(trans)-2-(l -methyl- lH-pyrazol-4- yl)cyclopropane-carbonyl)acrylate (1.0 g, 3.61 mmol) in ethanol (15 mL) was added 3- hydrazinylbenzoic acid hydrochloride (0.714 g, 3.79 mmol). To the resulting suspension was added TEA (1.256 mL, 9.01 mmol). The resulting clear solution was stirred for 1.0 hour at room temperature, after which LCMS showed a complete reaction. The mixture was concentrated and the residue was diluted with 30 mL aqueous 1.0 N HCl and extracted with ethyl acetate. The organic extract was concentrated to give the title compound as a yellow solid used in the next step without further purification (1.15 g, 3.14 mmol, 87 % yield). LC-MS mlz 367.0 (M+H)+, 0.83 min (ret. time). |
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