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CAS No. : | 624-84-0 | MDL No. : | MFCD00007589 |
Formula : | CH4N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XZBIXDPGRMLSTC-UHFFFAOYSA-N |
M.W : | 60.06 | Pubchem ID : | 12229 |
Synonyms : |
|
Num. heavy atoms : | 4 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 13.02 |
TPSA : | 55.12 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) : | -7.51 cm/s |
Log Po/w (iLOGP) : | 0.12 |
Log Po/w (XLOGP3) : | -1.19 |
Log Po/w (WLOGP) : | -1.39 |
Log Po/w (MLOGP) : | -1.2 |
Log Po/w (SILICOS-IT) : | -0.7 |
Consensus Log Po/w : | -0.87 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.6 |
Solubility : | 241.0 mg/ml ; 4.01 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 0.53 |
Solubility : | 202.0 mg/ml ; 3.36 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 0.65 |
Solubility : | 270.0 mg/ml ; 4.5 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.1 |
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 |
---|---|---|
90.3% | Stage #1: With sodium methylate In ethanol at 0 - 20℃; Stage #2: at 55℃; for 17 h; |
Example 3 Preparation of 3-Methyl-1,2,4-triazole; To a 20-L reactor equipped with a temperature probe and an overhead stirrer, was added acetamidine hydrochloride (2.0 kg, 21.16 mol) and absolute ethanol (10.0 L). The resulting slurry was cooled to 0-5° C. Sodium methoxide (1.15 kg, 21.2 mol) was added to the reactor with stirring while maintaining the batch temperature below 20° C. Subsequently, formic hydrazine (1.28 kg, 21.2 mol) was added to the reaction mixture. The resulting slurry was continuously stirred and heated to 55° C. over a period of 1 h and was allowed to agitate at 55° C. degree for 16 h. Then the reaction mixture was cooled to 20° C. and solids were filtered off. The filtrate was transferred back to the reactor and concentrated to 2.0-2.5 L though distillation under reduced pressure. To this concentrated ethanol solution, was charged butyl acetate (4 L) at room temperature. The resulting solution was concentrated to 2.0-2.5 L by distillation under reduced pressure. To this concentrated solution, was added additional butyl acetate (4.0 L) at room temperature and GC analysis of the solution was conducted. The above solvent exchange process was repeated until butyl acetate/ethanol wt/wt percent is greater than 19 by GC analysis. After the completion of solvent exchange process, the batch was heated to 70-75° C. and held for 15 min. Then the rich organic solution was cooled to ambient temperature (20-22° C.) over a 1 h period and was agitated at that temperature for 14 hours. The resulting slurry was cooled to 0-5° C. and agitated at that temperature for additional 1 hour. The crystals were collected by filtration. The cake was washed with 4.0 L of a mixture of heptane:butyl acetate (v/v: 3:1). The wet cake was de-liquored for 1 hour, and dried under vacuum (25 mmHg) at 30-35° C. for 48 h. 3-Methyl-1,2,4-triazole (1.59 kg, 19.1 mol) was obtained in 90.3percent yield as a light pink solids. 1H NMR (300 MHz) δ 2.53 (s, 3H), 8.03 (s, 1H), 11.52 (s, 1H); 13C NMR (300 MHz) δ 156.5, 149.8, 13.5. Anal. Calc. for C3H5N3: C, 43.36; H, 6.06; N, 50.57. Found: C, 43.29; H, 6.15; N, 50.54 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.3% | at 150℃; for 1.5 h; | Procedure: A solid mixture of formic hydrazide (68 g, 1.13 mol) and thioacetamide (85 g, 1.13 mol) in a 500 mL-RBF was heated with stirring at 150° C. (oil bath temp.) for 1.5 hrs with a gentle stream of nitrogen, removing H2S and water (about 18 mL of liquid collected) formed during the reaction. The reaction mixture was distilled under reduced pressure, collecting 60.3 g (0.726 mol, Y. 63.3percent) of the title compound at 102° C./0.35-1 mmHg as white solid after removing a liquid forerun.: 1H NMR (CDCl3) δ ppm 2.51 (3H, s, 3-Me), 8.03 (1H, s, 5-H), 9.5 (1H, br, NH); TLC Rf (10percent MeOH/CH2Cl2)=0.3 (phosphomolybdate-charring, white spot). Reference: Vanek, T.; Velkova, V.; Gut, Jiri Coll. Czech. Chem. Comm. 1985, 49, 2492. |
63.3% | at 150℃; | Procedure: A solid mixture of formic hydrazide (68 g, 1.13 mol) and thioacetamide (85 g, 1.13 mol) in a 500 mL-round bottom flask was heated with stirring at 150° C. (oil bath temp.) for 1.5 hrs with a gentle stream of nitrogen, removing H2S and water (about 18 mL of liquid collected) formed during the reaction. The reaction mixture was distilled under reduced pressure, collecting 60.3 g (0.726 mol, Y. 63.3percent) of the title compound at 102° C./0.35-1 mmHg as a white solid after removing a liquid forerun.: 1H NMR (CDCl3) δppm 2.51 (3H, s, 3-Me), 8.03 (1H, s, 5-H), 9.5 (1H, br, NH); TLC Rf (10percent MeOH/CH2Cl2)=0.3 (phosphomolybdate-charring, white spot). Reference: Vanek, T.; Velkova, V.; Gut, Jiri Coll. Czech. Chem. Comm. 1985, 49, 2492. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.80 g | Stage #1: at 5℃; for 1.5 h; Stage #2: With sodium hydrogencarbonate In methanol at 5 - 20℃; for 22.25 h; |
1.76 g (16.62 mmol) of bromocyanide,In 10 mL of methanol was added dropwise a solution of 1.0 g (16.65 mmol) of formol hydrazide in 10 mL of methanol under ice-cooling and stirring, the mixture was stirred at 5 ° C. or less for 1 hour and 30 minutes,1.82 g (21.6 mmol) of sodium hydrogencarbonate was added.After stirring at the same temperature for 15 minutes, the mixture was stirred for 22 hours while spontaneously raising the temperature to room temperature. After completion of the reaction was confirmed, insoluble matter was separated by filtration and the solvent was distilled off to obtain 3.12 g of a pale pink solid. Acetonitrile was added, insoluble matter was filtered off again, and the solvent was distilled off from the filtrate. The solid was washed with diethyl ether to obtain 0.80 g of the objective substance as a pale reddish white solid. |
0.8 g | Stage #1: at 5℃; for 1.5 h; Stage #2: With sodium hydrogencarbonate In methanol at 5℃; for 22.25 h; |
BromocyanineTo a solution of 1.76 g (16.62 mmol) of methanol in 10 mL, under ice-cooling and stirring,A solution of 1.0 g (16.65 mmol) of formohydrazide in 10 mL of methanol was added dropwise, and the mixture was stirred at 5 ° C. or less for 1 hour and 30 minutes, then 1.82 g (21.6 mmol) of sodium hydrogencarbonate was added. After stirring at the same temperature for 15 minutes, the mixture was stirred for 22 hours while spontaneously raising the temperature to room temperature. After confirming completion of the reaction, the insoluble matter was separated by filtration and the solvent was distilled off to obtain 3.12 g of a pale pink solid. Acetonitrile was added, insoluble matter was filtered off again, and the solvent was distilled off from the filtrate. The solid was washed with diethyl ether to obtain 0.80 g of the objective substance as a pale reddish white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | at 20 - 150℃; | Procedure: A solid mixture of formic hydrazide (6.0 g, 0.1 mol; Aldrich) and thiopropionamide (8.92 g, 0.1 mol; TCI) was heated with stirring at 150° C. (oil bath temp.) for 2 hrs with a gentle stream of nitrogen. It was cooled and stored at room temperature overnight. The solid reaction mixture was suspended in 20percent EtOAc/CH2Cl2, removing insoluble solid and the filtrate was concentrated. The residue was purified by column chromatography, eluting first with 50-80percent EtOAc/CH2Cl2, removing by-products, and then with 10percent MeOH/CH2Cl2, collecting 5.4 g (0.056 mol, Y. 56percent) of the title compound as a solid: MS (ESI -) m/z 96 (M-H); 1H NMR (CDCl3) δ ppm 1.37 (3H, t, J=7.5 Hz), 2.88 (2H, q, J=7.5 Hz), 8.06 (1H, s, 5-H), 9.4 (1H, br, NH). Reference: Vanek, T.; Velkova, V.; Gut, Jiri Coll. Czech. Chem. Comm. 1985, 49, 2492. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
140 g | With hydrazine hydrate In methanol; water at 0 - 60℃; for 24 h; | a) Preparation of Formyl Hydrazine A solution of hydrazine hydrate (138 g) and water (20 ml) was added slowly to a mixture of ethyl formate (200 g) and methanol (200 ml) by cooling the reaction mixture to 0-10° C. The reaction mixture was heated to 55-60° C. and stirred for 24 hours at 55-60° C. Distilled off the solvent under reduced pressure. Isopropanol was added to the obtained residue. The reaction mixture was cooled to 0-5° C. and stirred for 2 hours at 0-5° C. Filtered the solid, washed with isopropyl alcohol and then dried to get title compound. Yield: 140 g |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Stage #1: at 160℃; for 1.5 h; Stage #2: With water In 1-methyl-pyrrolidin-2-one at 25 - 100℃; for 0.25 h; |
To a solution of 4-bromo-2-cyano-phenyl)-carbamic acid ethyl ester (40.4 g, 150 mmol) in NMP (170 mL) was added formylhydrazine (10.0 g, 150 mmol). The resulting mixture was stirred for 1.5 h at 160° C. under a gentle nitrogen sweep. It was cooled to below 100° C. and water (340 mL) was added slowly. The resulting slurry was cooled to 25° C. and stirred for 15 min. The solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (32.4 g, 81percent) as a light yellow solid. MS: m/e=264.9/267.0 (M+H+). |
81% | Stage #1: at 160℃; for 1.5 h; Stage #2: With water In 1-methyl-pyrrolidin-2-one at 25 - 100℃; for 0.25 h; |
b) 9-Bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one To a solution of (4-bromo-2-cyano-phenyl)-carbamic acid ethyl ester (40.4 g, 150 mmol) in NMP (170 mL) was added formylhydrazine (10.0 g, 150 mmol). The resulting mixture was stirred for 1.5 h at 160° C. under a gentle nitrogen sweep. It was cooled to below 100° C. and water (340 mL) was added slowly. The resulting slurry was cooled to 25° C. and stirred for 15 min. The solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (32.4 g, 81percent) as a light yellow solid. MS: m/e 264.9/267.0 [M+H+]. |
81% | at 160℃; for 1.5 h; | To a solution of 4-bromo-2-cyano-phenyl)-carbamic acid ethyl ester (40.4 g, 150 mmol) in NMP (170 mL) was added formylhydrazine (10.0 g, 150 mmol). The resulting mixture was stirred for 1.5 h at 160° C. under a gentle nitrogen sweep. It was cooled to below 100° C. and water (340 mL) was added slowly. The resulting slurry was cooled to 25° C. and stirred for 15 min. The solid was collected by filtration and washed with water and 2-propanol. Drying in vacuo afforded the title compound (32.4 g, 81percent) as a light yellow solid. MS: m/e=264.9/267.0 [M+H+]. |
[ 563-41-7 ]
Hydrazinecarboxamide hydrochloride
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[ 563-41-7 ]
Hydrazinecarboxamide hydrochloride
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