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CAS No. : | 74205-82-6 | MDL No. : | MFCD00227137 |
Formula : | C3H5N3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WCRAKJMHCWUABB-UHFFFAOYSA-N |
M.W : | 99.09 | Pubchem ID : | 1547783 |
Synonyms : |
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 22.45 |
TPSA : | 50.94 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) : | -7.37 cm/s |
Log Po/w (iLOGP) : | 0.37 |
Log Po/w (XLOGP3) : | -0.65 |
Log Po/w (WLOGP) : | -0.92 |
Log Po/w (MLOGP) : | -1.03 |
Log Po/w (SILICOS-IT) : | -0.43 |
Consensus Log Po/w : | -0.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.51 |
Solubility : | 30.8 mg/ml ; 0.311 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.05 |
Solubility : | 112.0 mg/ml ; 1.13 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 0.21 |
Solubility : | 162.0 mg/ml ; 1.64 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.65 |
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 |
---|---|---|
89% | at 140℃; for 0.5 h; | Step 1. Preparation of (1H-1,2,4-triazol-1-yl)methanol A mixture of 1H-1,2,4-triazole (7.04 g, 102 mmol), paraformaldehyde (3.06 g, 102 mmol) and catalytic amount of triethylamine was heated to molten condition and stirred at the same temperature (140° C.) for 0.5 hour. Reaction mixture was then cooled to 30° C. to obtain the product (9.0 g, 89percent) as white solid. |
79% | at 20℃; for 13 h; Reflux | The compound was synthesized with some modifications compared to Ref. [14]: (1,2,4)-triazole [98 percent(Aldrich), 1,73 g, 25 mmol] in 20 ml of ethanol (absolute ethanol, ≥99.8 percent, Sigma-Aldrich) and 3.5 ml of formaldehyde solution (≥36,5 percent, Sigma-Aldrich) were stirred, refluxed for 1 h, and mixing was continued at room temperature for 12 h. After the elimination of the solvent under reduced pressure, the obtained residue was treated with cold water. A white solid appeared, which was collected by filtration, washed with diethyl ether (99 percent, Sigma-Aldrich) and dried under vacuum to yield the pure product (79 percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With triethylamine; at 140℃; for 0.5h; | Step 1. Preparation of (1H-1,2,4-triazol-1-yl)methanol A mixture of 1H-1,2,4-triazole (7.04 g, 102 mmol), paraformaldehyde (3.06 g, 102 mmol) and catalytic amount of triethylamine was heated to molten condition and stirred at the same temperature (140 C.) for 0.5 hour. Reaction mixture was then cooled to 30 C. to obtain the product (9.0 g, 89%) as white solid. |
79% | In ethanol; water; at 20℃; for 13h;Reflux; | The compound was synthesized with some modifications compared to Ref. [14]: (1,2,4)-triazole [98 %(Aldrich), 1,73 g, 25 mmol] in 20 ml of ethanol (absolute ethanol, ?99.8 %, Sigma-Aldrich) and 3.5 ml of formaldehyde solution (?36,5 %, Sigma-Aldrich) were stirred, refluxed for 1 h, and mixing was continued at room temperature for 12 h. After the elimination of the solvent under reduced pressure, the obtained residue was treated with cold water. A white solid appeared, which was collected by filtration, washed with diethyl ether (99 %, Sigma-Aldrich) and dried under vacuum to yield the pure product (79 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With thionyl chloride; In 1,2-dichloro-ethane; at 100℃; for 4h; | Step 2. Preparation of 1-(chloromethyl)-1H-1,2,4-triazole To a solution of <strong>[74205-82-6](1H-1,2,4-triazol-1-yl)methanol</strong> (1.0 g, 10.09 mmol) in dichloroethane (20 ml) thionyl chloride (1.105 ml, 15.14 mmol) was added and the reaction mixture was stirred at 100 C. for 4 hours. The reaction mixture was cooled to 30 C., poured into H2O (25 mL) and extracted with dichloromethane (3*20 mL). The combined organic layers was washed with H2O (50 mL) & brine solution (50 mL), dried over Na2SO4 and evaporated in rotavapor under vacuum to yield 1-(chloromethyl)-1H-1,2,4-triazole (0.570 g, 48%) as brown liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.2% | With thionyl chloride; In tetrahydrofuran; | Step 2--Preparation of 1-(chloromethyl)-1,2,4-triazole hydrochloride A 4 neck 1 liter flask equipped with condenser, addition funnel and mechanical stirrer was charged 45 gms of <strong>[74205-82-6]1-(hydroxymethyl)-1,2,4-triazole</strong> (0.464 mole) in 500 ml of THF was heating to 40 C. with vigorous stirring. Then SOCl2 (61 ml, 0.84 mole) was added dropwise maintaining the temperature at 45 C. During the addition, a precipitate formed and the mixture was stirred for an additional 2 hours. The product was filtered, washed three times with ethyl acetate and vacuum dried at room temperature. 67.3 gms of product having a melting point of 118-130 C. resulted (94.2% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.6% | Step 1--Preparation of 1-(hydroxymethyl)-1,2,4-triazole A 3 neck 500 ml round bottom flask equipped with condenser and mechanical stirrer was charged with 69.1 gms of triazole (1 mole), 30.1 gms of paraformaldehyde and 1 ml of triethylamine in 250 ml of THF. The reaction was stirred under nitrogen at reflux for 18 hours after which the mixture was concentrated on the rotovap. A white solid resulted which was filtered and washed with ether and gave 96.8 gms of product (97.6% yield) having a melting point of 67-70 C. The product can be further purified by dissolving in hot acetone, cooling to room temperature, filtering the solid and washing with ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; In potassium hydroxide; ethanol; chloroform; water; | PREPARATION EXAMPLE A (COMPOUND NO. 15) 2-(4-Chloro-2-fluoro-5-ethoxycarbonylmethoxyphenyl)-4, 5,6,7-tetrahydro-2H-isoindole-1,3-dione (4.0 g, made substantially by the methods described in EP 0 083 055 A2) and KOH (85%, 2.1 g) in 50 ml ethanol were stirred at room temperature for 1 hour and then evaporated to dryness. To the residue was added 100 ml chloroform and 8 ml SOCl2. The reaction mixture was then heated to reflux for 2 hours. Potassium chloride was filtered and washed with fresh chloroform. The filtrate was evaporated to dryness. To the residue was added 50 ml chloroform and 1.5 g 1-hydroxymethyl-(1H)-1,2,4-triazole. The reaction mixture was then stirred at room temperature for 5 hours. Water was added to the mixture, the organic layer was separated and washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography to give 2.1 g of 2-(4-chloro-2-fluoro-5-[(1,2,4-triazolylmethoxy)carbonylmethoxy]phenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (Compound No. 15). M.P. 151-154 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In acetonitrile; at 20℃; for 96h; | General procedure: A mixture containing 25 ml of acetonitrile, two equivalents of (3,5-dimethyl-1H-pyrazol-1-yl) methanol (compound 2), and one equivalent of N,N-Diethyl-propanediamine was stirred at room temperature for 4 days. Next, the solvent was concentrated at a reduced pressure, washed with brine and dichloromethane. The organic solution was dried with MgSO4, and the solvent was concentrated at reduced pressure to yield compound 3 as light yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With sulfuric acid; at 25℃; for 24h; | General procedure: To a solution of indolines 6 (1.0 mmol) dissolved in acid (1.0 ml) in an icebath was added (1H-1,2,4-triazol-1-yl)methanol 5 (ammount as given in Table 1). Themixture was then stirred under the temperature and time given in Table 1. After completion of the reaction (TLC), the reaction mixture was poured intoice water, and 20% NaOH solution was added slowly to adjust the pH to 9. The product was extracted with dichloromethane. After removal of the solvent, theresidue was chromatographed over silica gel using dichloromethane-methanol togive 7 (yield as given in Table 1). The analytical and spectroscopic data for 7b and 7c are given below |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With sulfuric acid; at 25℃; for 4h; | General procedure: To a solution of indolines 6 (1.0 mmol) dissolved in acid (1.0 ml) in an icebath was added <strong>[74205-82-6](1H-1,2,4-triazol-1-yl)methanol</strong> 5 (ammount as given in Table 1). Themixture was then stirred under the temperature and time given in Table 1. After completion of the reaction (TLC), the reaction mixture was poured intoice water, and 20% NaOH solution was added slowly to adjust the pH to 9. The product was extracted with dichloromethane. After removal of the solvent, theresidue was chromatographed over silica gel using dichloromethane-methanol togive 7 (yield as given in Table 1). The analytical and spectroscopic data for 7b and 7c are given below |
71% | With sulfuric acid; at 20℃; for 5h;Cooling with ice; | Example4. Synthesis of Intermediate 5Intermediate 4 (16.3g, 70.4 mmol) was completely dissolved in concentrated sulfuric acid (80ml) under ice bath, and triazolemethanol (10.4g) was added. The solution was stirred at room temperature for 5hrs. TLC was used toshow the completion of raw materials. Post-treatment: the reaction solution wasslowly added to 20% sodium hydroxide solution under ice bath. After alkalizing,dichloromethane was added to extract the product. The organic layer was driedand the solvent was removed by rotary evaporation. 21.2g yellow oil product(crude) was obtained. 15.6g light yellowsemi-solid (Intermediate 5) was obtained after column chromatography separation(dichloromethane: methanol 20: 1+ 1% triethylamine) and rotary evaporation,with a yield of 71.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile; for 4h;Reflux; | This compound was prepared from the condensation of four equivalents of 1H-(1, 2, 4)-triazol-1-ylmethanol (10 mmol, 1 g) with one equivalent of ethane-1,2-diamine (?99,0 %, Fluka, 2,5 mmol, 0,15 g) in anhydrous acetonitrile (?99,8 %, Sigma-Aldrich) as the solvent. The mixture was stirred under reflux for 4 h. Then, the solution was dried over anhydrous MgSO4. After filtration, the solvent was removed under reduced pressure and the obtained residue was washed with a mixture of dichloromethane (99.8 %, Sigma-Aldrich) and diethyl ether (3/1 ratio) to give an oily product, which was recrystallized with ethanol to yield white crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46.6% | The indoline (1) (10.0 (^, 0.08311101) was added to a 11 round bottom flask, Glacial acetic acid 1001111, stirring at room temperature 0.5h, adding triazole methyl alcohol (16.61 g, 0.167 mol), and the reaction was stirred at 80 C for 3 h. TLC indicated that the reaction was complete and stopped The reaction was cooled to room temperature, 40% aqueous sodium hydroxide (100 ml) and 100 ml of methanol were added under ice-cooling, refluxed for 0.5 h at 70 C, Dichloromethane (75 mL x 3), saturated brine (150 ml x 2), dried over anhydrous sodium sulfate and concentrated to give Yellow oil 7.74 g (2), yield 46.6% |
Tags: 74205-82-6 synthesis path| 74205-82-6 SDS| 74205-82-6 COA| 74205-82-6 purity| 74205-82-6 application| 74205-82-6 NMR| 74205-82-6 COA| 74205-82-6 structure
[ 135242-93-2 ]
(1-Methyl-1H-[1,2,4]triazol-3-yl)methanol
Similarity: 0.64
[ 49607-51-4 ]
1-Methyl-1H-1,2,4-triazol-3-amine
Similarity: 0.65
[ 135242-93-2 ]
(1-Methyl-1H-[1,2,4]triazol-3-yl)methanol
Similarity: 0.64
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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