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CAS No. : | 16865-11-5 | MDL No. : | MFCD09835289 |
Formula : | C7H3Cl3N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SUQYOUJCBGMSLV-UHFFFAOYSA-N |
M.W : | 221.47 | Pubchem ID : | 286009 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 51.12 |
TPSA : | 28.68 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.02 cm/s |
Log Po/w (iLOGP) : | 1.71 |
Log Po/w (XLOGP3) : | 3.7 |
Log Po/w (WLOGP) : | 3.52 |
Log Po/w (MLOGP) : | 2.74 |
Log Po/w (SILICOS-IT) : | 3.93 |
Consensus Log Po/w : | 3.12 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.1 |
Solubility : | 0.0176 mg/ml ; 0.0000796 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.99 |
Solubility : | 0.0225 mg/ml ; 0.000102 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.77 |
Solubility : | 0.0038 mg/ml ; 0.0000171 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.53 |
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 |
---|---|---|
90% | Stage #1: for 3 h; Reflux Stage #2: With sodium hydroxide In water at 20℃; |
Thoroughly dried 5,6-dichloro- 1 ,3-dihydro-benzoimidazol-2-one (28.4 g, 0.14 mol) was suspended in POCI3 (75 ml_). The reaction solution was heated to reflux temperature for 3 hours and cooled to room temperature. The solution was poured into crushed ice/water (1.5 L) slowly with sufficient stirring. The solution was neutralized to pH = 7.0 with NaOH. The precipitated solid was collected by filtration, washed with water, and dried to afford the title compound (27.9 g, 90percent). The crude product was used in the following reaction without further purification. |
71% | at 120℃; for 2 h; a screw-cap pressure tube | (b) Preparation of the intermediary compound 2,5,6-trichloro-l -benzo[d]imidazole:To 5,6-dichloro-lH-benzo[d]imidazol-2(3H)-one (1.0 g, 4.5 mmol) was added phosphoryl trichloride (4 mL) and the reaction mixture was heated in a screw-cap pressure tube at 12O0C for 2 hours. The reaction mixture was concentrated in vacuo, the residue was diluted with water (30 mL) and the resulting off-white solid was filtered off. The precipitate was washed with water (3x20 mL) and dried under high vacuum to afford 0.77 g (71 percent yield) of 2,5,6-trichloro-lH- benzo[d]imidazole. |
71% | at 120℃; for 2 h; | To 5,6-dichloro-lH-benzo[d]imidazol-2(3H)-one (1.0 g, 4.5 mmol) was added phosphoryl trichloride (4 mL) and the reaction mixture was heated in a screw-cap pressure tube at 120°C for 2 hours. The reaction mixture was concentrated in vacuo, the residue was diluted with water (30 mL) and the resulting off-white solid was filtered off. The precipitate was washed with water (3 x20 mL) and dried under high vacuum to afford 0.77 g (71 percent yield) of 2,5,6-trichloro-lH- benzo[d]imidazole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49.5% | With sodium nitrite In methanol; chloroform; water | Method B A CuCl2 saturated aqueous solution (15 ml) was diluted to 25 ml with water. Sodium nitrite (1.035 g, 5 mmole) was dissolved in 5 ml of water and slowly added to the CuCl2 solution. After two minutes, 2-amino-5,6-dichlorobenzimidazole (0.935 g, 5 mmole) was slowly added in small portions. The mixture was stirred at room temperature for 1 hr. Excess CuCl2 solution was added and the mixture was heated on a steam bath for 1 hr. The aqueous solution was then extracted with ethyl acetate (3*50 ml) and the organic layer was washed with brine, dried with MgSO4, concentrated, and separated on a silica column using 2percent MeOH/CHCl3 to afford 545 mg (49.5percent) of 2,5,6-trichlorobenzimidazole. 1 H NMR, TLC, and MS analysis were identical to the same compound obtained by Method A. |
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