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CAS No. : | 17289-25-7 | MDL No. : | MFCD06738905 |
Formula : | C5H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NLEAEGDBKRBJAP-UHFFFAOYSA-N |
M.W : | 112.13 | Pubchem ID : | 7060524 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 29.62 |
TPSA : | 38.05 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) : | -7.58 cm/s |
Log Po/w (iLOGP) : | 0.9 |
Log Po/w (XLOGP3) : | -0.84 |
Log Po/w (WLOGP) : | -0.24 |
Log Po/w (MLOGP) : | -0.94 |
Log Po/w (SILICOS-IT) : | 0.19 |
Consensus Log Po/w : | -0.19 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.4 |
Solubility : | 44.4 mg/ml ; 0.396 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.52 |
Solubility : | 373.0 mg/ml ; 3.32 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.57 |
Solubility : | 30.4 mg/ml ; 0.271 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.54 |
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 |
---|---|---|
78.95% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 50℃; | To a suspension of 1-methyl-imidazole-4-carboxylic acid [(11.] 4g, 90 [MMOL)] in THF (500ml) at [0°C,] was added dropwise lithium aluminium hydride (solution 1 M in THF, [117MOL,] 117 [MMOL)] and the mixture was stirred at room temperature overnight and then at [50°C] for 1 hour. Then water (3 mi) was added followed by [NA2S04,] and the resulting precipitate was filtered off on [A] [CELITE PAD. THE FILTRATE] was concentrated under reduced pressure to afford the title compound as a solid (8g, 78.95percent) ;'H NMR (300 MHz, CDCl3, ppm) [8] : 7.25 (s, [1 H),] 6.7 (s, [1H),] 5.25 (m, [1 H),] 4.4 (s, 2H), [3.] 45 (s, 3H). |
78.95% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 50℃; for 1 h; Stage #2: With water; sodium sulfate In tetrahydrofuran |
To a suspension of [1-METHYL-IMIDAZOLE-4-CARBOXYLIC] acid [(11.] 4g, 90 [MMOL)] in THF (500ml) at [0°C WAS] added dropwise LiAIH4 (solution 1 M in THF, 117ml. 117 [MMOL)] and the mixture was stirred at room temperature overnight and then at [50°C] for 1 hour. On cooling, water (3 [ML)] was added followed by [NA2SO4,] and the resulting precipitate was filtered through a celite pad. The filtrate was concentrated under reduced pressure to afford the title compound as a solid (8g, 78.95percent) [; H] NMR (300 MHz, CDCl3) [] ppm: [7. 25] (s, [1 H),] 6.7 (s, [1 H),] 5.25 (m, [1 H),] 4.4 (s, 2H), 3.45 (s, 3H). |
78.95% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 50℃; | To a suspension of [1-METHYL-IMIDAZOLE-4-CARBOXYLIC ACID (11.] 4g, 90 [MMOL)] in THF (500ml) at [0°C,] was added drop-wise a solution of lithium aluminium hydride [(1 M] in THF, [117ML,] 117 [MMOL)] and the mixture was stirred at room temperature overnight and then at [50°C] for 1 hour Water (3 [ML)] was added followed by [NA2SO4] and the mixture was filtered through [CELITETM.] The filtrate was concentrated under reduced pressure to afford the title compound as a solid [(8G,] 78.95percent) ;'H NMR (300 MHz, [CDCI3)] 6 ppm: 7.25 (s, 1 H), 6. 7 (s, 1H), 5.25 (m, 1H), 4.4 (s, 2H), 3.45 (s, 3H). |
47.5% | With lithium aluminium tetrahydride In tetrahydrofuran at 50℃; for 12 h; Inert atmosphere | 190a) (1 -Methyl-1 H-imidazol-4-yl)methanol A solution of 1 -methyl-1 H-imidazole-4-carboxylic acid (25 g, 198 mmol) in tetrahydrofuran (THF) (1000 ml_) was added LiAlhU (15.05 g, 396 mmol) slowly under nitrogen at room temperature. The reaction mixture was stirred at 50 °C for 12 h. It was added 15 mL of water, 15 mL of 10percent NaOH, 45 mL of water to the reaction mixture at 0 °C. The solid was filtered and the filtrate was concentrated to obtain the title compound (1 -methyl-1 H- imidazol-4-yl)methanol (13.2 g, 94 mmol, 47.5 percent yield) which was used for next step without further purification. LC-MS m/z 1 13.1 (M+H)+, 0.33 min (ret. time). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With manganese(IV) oxide In acetone at 60℃; for 12 h; Inert atmosphere | 190b) 1 -Methyl-1 H-imidazole-4-carbal A solution of (1 -methyl-1 H-imidazol-4-yl)methanol (5 g, 44.6 mmol) in acetone (50 mL) was added manganese(IV) oxide (19.38 g, 223 mmol) slowly under nitrogen at room temperature. The reaction mixture was stirred at 60 °C for 12 h. The solid was filtered and the liquid was concentrated to obtain the title compound 1 -methyl-1 H-imidazole-4- carbaldehyde (4.12 g, 34.4 mmol, 77 percent yield) which was used in next step without further purification. LC-MS m/z 1 1 1 .2 (M+H)+, 0.49 min (ret. time). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.81% | With thionyl chloride In dichloromethane at 0 - 20℃; Heating / reflux | To a solution of intermediate 1 (5g, 44.64 [MMOL)] in CH2CI2 [(10 MI)] at [0°C] was added dropwise thionyl chloride (50 [ML)] and then the mixture was stirred at room temperature overnight and then under reflux for 3 hours and then concentrated under reduced pressure. The residue was treated with diethyl oxide and the resulting precipitate was filtered and dried. The title compound was obtained as a brown solid [(4G,] 53. 80percent); 1HNMR (300 MHz, [DS-DMSO, PPM). S] : 9.25 (s , 1H), 7.8 (s, 1H), 4.95 (s, 2H), 3.9 (s, 3H). |
53.81% | With thionyl chloride In dichloromethane at 20℃; for 3 h; | To a solution of intermediate 22 (5g, 44.64 [MMOL)] in [CH2CI2] (10 ml) at [0°C] was added dropwise thionyl chloride (50 mi) and then the mixture was stirred at room temperature overnight and then at reflux for 3 hours. The mixture was concentrated under reduced pressure, and diethyl ether added. The resulting precipitate was filtered and dried to give the title product as a brown solid (4g, 53. [81percent) ;APOS;H] NMR (300 MHz, [D6-DMSO)] [] ppm: 9.25 (s, [1 H),] 7.8 (s, 1H), 4. 95 (s, 2H), 3.9 (s, 3H). |
53.81% | With thionyl chloride In dichloromethane at 0 - 20℃; Heating / reflux | To a solution of intermediate 6 (5g, 44.64 [MMOL)] in CH2CI2 (10 ml) at [0°C] was added dropwise thionyl chloride (50 mi) and the mixture was stirred at room temperature overnight and then at reflux for 3 hours. The mixture was concentrated under reduced pressure and the residue taken up in diethyl ether to give a precipitate. The precipitate was filtered and dried to give the title compound [(4G,] 53. [81 percent) ;APOS;H] NMR (300 MHz, [DMSO-D6)] [6] ppm : 9.25 (s, [1 H),] 7.8 (s, [1 H),] 4.95 (s, 2H), 3.9 (s, [3H).] |
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