Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 670-83-7 | MDL No. : | MFCD07772899 |
Formula : | C15H12N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FHHCKYIBYRNHOZ-UHFFFAOYSA-N |
M.W : | 220.27 | Pubchem ID : | 296732 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 17 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 69.46 |
TPSA : | 28.68 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.24 cm/s |
Log Po/w (iLOGP) : | 2.18 |
Log Po/w (XLOGP3) : | 3.39 |
Log Po/w (WLOGP) : | 3.74 |
Log Po/w (MLOGP) : | 2.76 |
Log Po/w (SILICOS-IT) : | 4.12 |
Consensus Log Po/w : | 3.24 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.95 |
Solubility : | 0.0248 mg/ml ; 0.000112 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.67 |
Solubility : | 0.047 mg/ml ; 0.000213 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -6.28 |
Solubility : | 0.000117 mg/ml ; 0.00000053 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.31 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
70% | In water; at 80℃; for 3h; | General procedure: To a stirred solution of aryl thioamide or amidine (1 mmol) in 5 mL distilled water was added alpha-tosyloxyketone (1 mmol) and the reaction mixture stirred at 60 C or 80 C till completion. Progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, product was readily filtered and recrystallized from ethanol (3a-k, 3p-o and 4a-e). In some cases (3l-m and 4f-i) product was extracted with dichloromethane (25 mL), washed with brine (25 mL), the organic layers were combined, dried over anhydrous Na2SO4 and distilled off in vacuum. The residue so obtained was purified by column chromatography on silica gel (100-200 mesh) (EtOAc/Hexane) to give pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With palladium diacetate; magnesium oxide; triphenylphosphine In 1,4-dioxane at 150℃; for 12h; | |
81% | With palladium diacetate; magnesium oxide; triphenylphosphine In 1,4-dioxane at 150℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In DMF (N,N-dimethyl-formamide); water; at 40℃; for 16h; | a. 1-Ethyl-<strong>[670-83-7]2,4-diphenyl-1H-imidazole</strong> 50% aqueous KOH (40 mmol) and iodoethane (40 mmol) are added to a solution of <strong>[670-83-7]2,4-diphenyl-1H-imidazole</strong> (30 mmol) in DMF (50 mL), and the mixture is stirred at 40 C. under nitrogen for 16 hours. The reaction mixture is partitioned between water (300 mL) and ethyl acetate (200 mL). The organic layer is separated, washed with water (200 mL*2), dried over anhydrous magnesium sulfate, filtered and evaporated at reduced pressure. The residue is dissolved in xylenes (100 mL) and evaporated at reduced pressure. Chromatography on silica gel (chloroform) provides pure 1-ethyl-<strong>[670-83-7]2,4-diphenyl-1H-imidazole</strong>. 13C NMR (400 MHz, CDCl3) delta=16.16, 41.43, 115.44, 124.57, 126.36, 128.26, 128.32, 128.54, 128.68, 130.55, 134.04, 140.87, 147.48. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; water; | SYNTHESIS EXAMPLE 1 [SYNTHESIS OF COMPOUND EXAMPLE (2)] Synthesis of 2,4-diphenylimidazole A dissolution of 7 g of a benzamidine chloride was made in 30 ml of water. The resulted solution was further added with a solution of 5 g of caustic potash dissolved in 15 ml of water, so that benzamidine was deposited. The resulted matter was added with 20 ml of chloroform and the whole amount of the solution was poured into a separating funnel and was then shaked well so as to separate a chloroform layer. The resulted chloroform solution was added with 3.0 g of bromoacetophenone while stirring and, next, the resulted solution was boiled and refluxed for 3 hours. When the chloroform was vacuum-distilled off therefrom, an oily matter remained. When the oily matter was washed well several times in warm water, it was crystallized. Next, when it was recrystallized with 10 ml of alcohol, 2.0 g of a white powder were obtained. Melting point: 168 to 175 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49.3% | With potassium hydroxide; paraformaldehyde; In methanol; chloroform; water; | EXAMPLE 3 2,5-diphenyl-4-hydroxymethyl-imidazole hydrochloride 5 g (0.0227 mole) of <strong>[670-83-7]2,4-diphenyl-imidazol</strong>e, 0.85 g (0.0283 mole) of paraformaldehyde and 0.1 g of finely ground potassium hydroxide are dissolved in 29 ml of warm methanol and heated under reflux for 90 hours. The solution is then decolourized with activated carbon, filtered and dried. Water and chloroform are added to the residue by stirring; the insoluble solid of both the layers is filtered, washed with water and chloroform and dried. 2.8 g (yield 49.3%) of crude product is thus obtained, which is crystallized from methanol to afford 1.1 g of 2,5-diphenyl-4-hydroxymethyl-imidazole, m.p. 206-207 C. (dec.) By the usual techniques the hydrochloride has been obtained, m.p. about 220 C. (dec.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With ammonium acetate; triethylammonium acetate; In neat (no solvent); at 120℃; for 0.5h; | General procedure: A mixture of benzil or benzoin (1 mmol), the aldehyde (1 mmol), ammonium acetate (0.55 g, 7 mmol) and TEAA (0.1 ml) was stirred at 120C in oil bath for the time show in Table 2. After completion of the reaction as indicated by TLC (hexane-ethyl acetate, 8:2), the mixture was cooled to room temperature, hot 96% EtOH (1 ml) was added and the mixture was stirred for 2 min. It was then poured onto crushed ice and the solid products that separated out were collected, washed with water, dried and recrystallized from ethanol (96%, 6 ml) to afford the pure 2,4,5-trisubstituted imidazole derivatives (5). All the products are known compounds and were characterized by the mps, IR and 1H NMR spectra. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; In 1,4-dioxane; at 80℃; for 24h; | A solution of Pd(PPh3)4 (6.9 mg, 6.0 mumol) and oxadiazolone 3a (56.1 mg, 0.20 mmol) in 1,4-dioxane (1.5 mL) was stirred at 80 C for 24 h. The reaction mixture was filtered through a pad of Florisil and the filtrate was concentrated under vacuum. The residue was subjected to column chromatography on Florisil (hexane/EtOAc = 4/1) to afford 43.8 mg of 4a (0.20 mmol, 99% yield) as a white solid (mp 160.1-160.5 C). 1H NMR (CDCl3): delta7.22-7.45 (m, 7H), 7.75 (d, J = 7.4 Hz, 2H), 7.87 (d, J = 7.3 Hz, 2H). 13C NMR (acetone-d6):delta 114.3, 125.4, 125.9, 127.2, 129.0, 129.3, 129.5, 131.8, 135.6, 142.6, 147.4. HRMS (FAB)calcd for C15H13N2 (M+H)+ 221.1079, found 221.1069. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 38% 2: 27% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In water; N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With copper(ll) sulfate pentahydrate; potassium carbonate; In N,N-dimethyl-formamide; at 150℃; for 48h;Inert atmosphere; Schlenk technique; | A mixture of 65 <strong>[670-83-7]2,4-diphenyl-1H-imidazole</strong> (I) (1.26g, 4.0mmol), 8 2-bromopyridine (1.63g, 24.0mmol), 66 K2CO3 (2.21g, 16.0mmol) and 9 CuSO4·5H2O (0.025g, 0.157mmol) in 67 DMF was heated to 150C for 48h. The reaction mixture was then allowed to cool to ambient temperature. Reaction mixture was diluted with dichloromethane (50mL) and the organic part was washed thrice (3×30mL) with water. The organic part was dried over anhydrous Na2SO4 and filtered. Removal of the solvent gave a colorless 68 solid. Analytically pure product 69 2-(2,4-diphenyl-1H-imidazol-1-yl)pyridine (II) was obtained by column chromatography using dichloromethane: methanol (95:5, v:v) as eluent. Yield: 37%. Compound 69 II (4.284g, 16.3mmol) and 10 iodomethane (3.1mL, 50mmol) were refluxed in acetonotrile (50mL) for 16h. Acetonitrile was then removed by distillation and washed with diethyl ether (3 X 30mL) to give analytically pure 11 3-methyl-2,4-diphenyl-1-(pyridin-2-yl)-1H-imidazol-3-ium iodide salt (III) with yield 97%. Compound III (0.5g) was dissolved in methanol and passed through ion exchange resin DOWEX (2g) packed in a column using methanol. Methanol was removed under reduced pressure to obtain ligand B as colorless solid compound with yield 89%. 1H NMR (400MHz, CDCl3, 25C, TMS): delta 8.56 (s, 1H), 7.87 (d, 1H), 7.78-7.82 (m, 5H), 7.58-7.68 (m, 6H), 7.40-7.49 (m, 2H), 3.85 (s, 3H) ppm. 13C NMR (100MHz, CDCl3, 25C, TMS): delta 149.1, 147.0, 144.4, 139.2, 135.6, 132.2, 130.8, 130.2, 129.8, 129.2, 128.8, 125.1, 124.6, 121.2, 120.5, 118.9, 34.7ppm. Elemental analysis: Anal. Calcd for C21H18ClN3: C, 72.51; H, 5.22; N, 12.08. Found: C, 72.59; H, 5.28; N, 12.15. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; In dichloromethane; at 100℃; for 10h;Sealed tube; | Into a 15mL pressure tube, sequentially add 1p (66.1 mg, 0.3 mmol), dichloromethane (3 mL), 2h (68.5 mg, 0.45 mmol), dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer (4.7 mg, 0.0075 mmol) and silver acetate (100.1 mg, 0.6 mmol), then the pressure-resistant tube was sealed and placed in a 100 C. oil bath for 10 h. After the reaction was completed, the mixture was cooled to room temperature, filtered with suction, dried, and separated through a silica gel column (dichloromethane / methanol / acetic acid = 30/1 / 0.1) to obtain a white solid product 3jj (62.2 mg, 56%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; In dichloromethane; at 100℃; for 10h;Sealed tube; | Into a 15mL pressure tube, sequentially add 1p (66.1mg, 0.3mmol), dichloromethane (3mL), 2a (84.7mg, 0.45mmol), dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer (4.7mg, 0.0075 mmol) and silver acetate (100.1 mg, 0.6 mmol), then the pressure-resistant tube was sealed and placed in a 100 C. oil bath for 10 h. After the reaction was completed, the mixture was cooled to room temperature, filtered with suction, dried, and separated through a silica gel column (dichloromethane / methanol / acetic acid = 30/1 / 0.1) to obtain 3p (85.4 mg, 70%) as a white solid product. |
[ 827-43-0 ]
4-Methyl-2-phenyl-1H-imidazole
Similarity: 0.91
[ 29914-81-6 ]
1,3-Bis(1H-benzo[d]imidazol-2-yl)benzene
Similarity: 0.89
[ 13739-48-5 ]
2-Methyl-4-phenyl-1H-imidazole
Similarity: 0.88
[ 864825-23-0 ]
(S)-1-(4-Phenyl-1H-imidazol-2-yl)ethanamine
Similarity: 0.84
[ 68282-47-3 ]
2-Phenyl-1H-imidazole-4-carbaldehyde
Similarity: 0.83
[ 827-43-0 ]
4-Methyl-2-phenyl-1H-imidazole
Similarity: 0.91
[ 13739-48-5 ]
2-Methyl-4-phenyl-1H-imidazole
Similarity: 0.88
[ 864825-23-0 ]
(S)-1-(4-Phenyl-1H-imidazol-2-yl)ethanamine
Similarity: 0.84
[ 68282-47-3 ]
2-Phenyl-1H-imidazole-4-carbaldehyde
Similarity: 0.83