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CAS No. : | 84661-56-3 | MDL No. : | MFCD00159695 |
Formula : | C7H8N4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UYHHYFDKCLECEJ-UHFFFAOYSA-N |
M.W : | 148.17 | Pubchem ID : | 134811 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 40.06 |
TPSA : | 35.64 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.25 cm/s |
Log Po/w (iLOGP) : | 0.95 |
Log Po/w (XLOGP3) : | -0.07 |
Log Po/w (WLOGP) : | 0.59 |
Log Po/w (MLOGP) : | -0.88 |
Log Po/w (SILICOS-IT) : | -0.08 |
Consensus Log Po/w : | 0.1 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.26 |
Solubility : | 8.23 mg/ml ; 0.0556 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.23 |
Solubility : | 87.9 mg/ml ; 0.593 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.32 |
Solubility : | 7.03 mg/ml ; 0.0474 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.18 |
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 |
---|---|---|
60% | at 50℃; for 12 h; | To a stirring solution of imidazole (3.0 g,44 mM) in 100 mL of dichloromethane, potassium hydroxide (4.94 g, 88 mM) was added.The mixture was refluxed at 50 °C for 12 h. The solvent was decanted and volatiles wereremoved to afford 1,1-methylene bis(imidazole) as a white solid, washed with ether anddried. General reaction involved in the preparation of the title compound is shown inscheme 1. White powder. Yield: 3.82 g (60percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.3% | Stage #1: Heating Stage #2: at 50 - 70℃; |
2 Bridged Imidazoles 2.1 Synthesis of 1,1'-methylenediimidazole 4 (Diez-Barra, E. et al., Phase transfer catalysis without solvent. Synthesis of bisazolylalkanes. Heterocycles 1992, 34, (7), 1365-1373) A mixture of 30 mmol of imidazole (2.040 g), 60 mmol of finely powdered potassium hydroxide (3.360 g) and a spatula-tip of tert-butylammonium bromide is heated cautiously and stirred efficiently until it becomes liquid. After cooling, 15 mmol of diiodomethane (4.000 g; 1.21 ml) are added. Subsequently, the mixture is heated to 50° C. for 90 minutes and to 70° C. for a further 90 minutes. The resulting mixture is extracted twice with 10 ml of ethanol, the solvent is removed and the residue is sublimed. Empirical formula: C7H8N4 M=148.174 g/mol Yield: 1.053 g (47.3percent of theory) Melting point: 154.8° C. 1H NMR (ppm, CDCl3, 300.13 MHz): 7.93 (s, 2H, NCN); 7.39 (s, 2H, NCHCN); 6.90 (s, 2H, NCCHN); 6.21 (s, 2H, NC2N) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium hydroxide; at 50℃; for 12h; | To a stirring solution of imidazole (3.0 g,44 mM) in 100 mL of dichloromethane, potassium hydroxide (4.94 g, 88 mM) was added.The mixture was refluxed at 50 C for 12 h. The solvent was decanted and volatiles wereremoved to afford 1,1-methylene bis(imidazole) as a white solid, washed with ether anddried. General reaction involved in the preparation of the title compound is shown inscheme 1. White powder. Yield: 3.82 g (60%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In acetonitrile;Schlenk technique; Reflux; Green chemistry; | General procedure: A mixture of 1a (100mg, 0.675mmol) or 1b (100mg, 0.526mmol) and benzyl chloride (for 1a: 155muL, 1.35mmol; for 1b: 121muL, 1.052mmol) was dissolved in CH3CN (5mL) in a Schlenk tube and stirred overnight under reflux temperature until the appearance of a white precipitate. The resulting hot solution was filtered and the precipitate was washed with 2×5mL cold CH3CN, and once with 5mL acetone, respectively, and then dried under vacuum. White powder. Yield: 78% for 2a (211mg); 76% for 2b (177mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In butan-1-ol; for 5h;Heating / reflux; | The combination of two equivalents of 1-IODOETHANOL (formula 12) with bisimidazol (formula 11) in refluxing butanol gives the water soluble diol shown as formula 13. This compound has been characterized by both NMR and X-ray crystallography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In butan-1-ol; for 12h;Heating / reflux; | A similar reaction has been carried out using 1,2-dibromoethane (formula 14) with bisimidazol to form the carbene represented by formula 15. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46.3% | 2 ml of benzyl bromide in 8 ml of tetrahydrofuran are added to 0.0034 mol of 1,1'-methylenediimidazole 4 in an ACE pressure tube, and the mixture is stirred at room temperature for 4 days. The precipitated solid is washed with tetrahydrofuran and then taken up in acetonitrile, admixed once again with 1 ml of benzyl bromide and stirred at 60 C. for 24 hours, at room temperature for 3 days and at 80 C. for a further 30 hours. The resulting solid is filtered off, washed again with tetrahydrofuran and dried. This forms a white solid 19. Empirical formula: C21H22N4Br2 M=490.234 g/mol Yield: 0.771 g (46.3% of theory) Melting point: decomposition at >248 C. 1H (ppm, d6-DMSO, 300.13 MHz): delta=9.68 (s, 2H, NCN); 8.11 (s, 2H, NCCHN); 7.93 (s, 2H, NCHCN); 7.44 (m, 10H, J=5.0 Hz, arom. C); 6.71 (s, 2H, NC2N); 5.52 (s, 4H, N-C2-C6H5) | |
With sodium hydroxide; In 1,4-dioxane; for 24h; | Dissolve NaOH (0.1mol, 4g) with 45ml of acetonitrile, weigh out imidazole (0.1mol, 6.8g), slowly add it to the reaction bottle with stirring at 60C, and add dibromomethane (0.05mol, 8.692g) to the dropping funnel ) And 15ml of acetonitrile, 1h after the completion of dripping stir the reaction at 80C for 3h to synthesize biimidazole. Weigh biimidazole (0.005mol, 0.7408g) and dissolve it with 30ml 1,4-dioxane, weigh benzyl bromide (0.011mol, 1.8813g) and add 15ml 1,4-dioxane to mix, slowly The ligand (L1) was synthesized in the reaction flask after 24 hours. Weigh benzimidazole (0.1mol, 11.8g) dissolved in 35ml of tetrahydrofuran, slowly add NaH (0.1mol, 2.4g) to the reaction flask, weigh dibromomethane (0.05mol, 8.692g) and add 35ml of acetonitrile to mix, then add In the reaction flask, the ligand (L2) was synthesized by reacting at 80C for 24h. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.3% | 2 Bridged Imidazoles 2.1 Synthesis of 1,1'-methylenediimidazole 4 (Diez-Barra, E. et al., Phase transfer catalysis without solvent. Synthesis of bisazolylalkanes. Heterocycles 1992, 34, (7), 1365-1373) A mixture of 30 mmol of imidazole (2.040 g), 60 mmol of finely powdered potassium hydroxide (3.360 g) and a spatula-tip of tert-butylammonium bromide is heated cautiously and stirred efficiently until it becomes liquid. After cooling, 15 mmol of diiodomethane (4.000 g; 1.21 ml) are added. Subsequently, the mixture is heated to 50 C. for 90 minutes and to 70 C. for a further 90 minutes. The resulting mixture is extracted twice with 10 ml of ethanol, the solvent is removed and the residue is sublimed. Empirical formula: C7H8N4 M=148.174 g/mol Yield: 1.053 g (47.3% of theory) Melting point: 154.8 C. 1H NMR (ppm, CDCl3, 300.13 MHz): 7.93 (s, 2H, NCN); 7.39 (s, 2H, NCHCN); 6.90 (s, 2H, NCCHN); 6.21 (s, 2H, NC2N) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | In acetonitrile; at 100℃; for 16h;Sealed tube; | l, l'-Methylenebis[imidazole] (0.500 g, 3.38 mmol) and 1,3-propane sultone (2.083 g, 17.05 mmol) were measured into a high pressure Pyrex tube. MeCN (10 mL) was added, and the vial was sealed and heated to 100 C for 16 hours. After cooling to room temperature the white precipitate formed was collected and washed thoroughly with MeOH and DCM before being dried in vacuo at room temperature. Ligand 2a was collected as a dry white powder (0.768 g, 1.96 mmol, 58%) NMR (400 MHz, D2O) delta 7.84 (d, J = 2.2 Hz, 2H), 7.75 (d, J = 2.2 Hz, 2H), 6.75 (s, 2H), 4.49 (t, J = 7.2 Hz, 4H), 2.99 (t, J = 7.3 Hz, 5H), 2.39 (p, J = 7.2 Hz, 4H). |
58% | In acetonitrile; at 100℃; for 16h; | 1,1-Methylenebis[imidazole] (0.500 g, 3.38 mmol)and 1,3-propane sultone (2.083 g, 17.05 mmol) were measured intoa high pressure Pyrex tube. MeCN (10 mL) was added, and the vialwas sealed and heated to 100 C for 16 hours (Scheme S3). |
Tags: 84661-56-3 synthesis path| 84661-56-3 SDS| 84661-56-3 COA| 84661-56-3 purity| 84661-56-3 application| 84661-56-3 NMR| 84661-56-3 COA| 84661-56-3 structure
[ 104619-51-4 ]
Di(1H-imidazol-1-yl)methanimine
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[ 1450-94-8 ]
1-Methyl-1H-imidazol-2-amine hydrochloride
Similarity: 0.84
[ 1588441-15-9 ]
1-Methyl-1H-imidazol-5-amine hydrochloride
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