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CAS No. : | 83741-35-9 | MDL No. : | MFCD09754164 |
Formula : | C7H5BrN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MUQFMGBYYAOIJK-UHFFFAOYSA-N |
M.W : | 197.03 | Pubchem ID : | 11252584 |
Synonyms : |
|
Num. heavy atoms : | 10 |
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 : | 43.79 |
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) : | -5.95 cm/s |
Log Po/w (iLOGP) : | 1.3 |
Log Po/w (XLOGP3) : | 2.18 |
Log Po/w (WLOGP) : | 2.33 |
Log Po/w (MLOGP) : | 1.75 |
Log Po/w (SILICOS-IT) : | 2.75 |
Consensus Log Po/w : | 2.06 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.1 |
Solubility : | 0.156 mg/ml ; 0.000793 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.42 |
Solubility : | 0.757 mg/ml ; 0.00384 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.77 |
Solubility : | 0.0337 mg/ml ; 0.000171 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.49 |
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 |
---|---|---|
97% | at 100℃; for 2 h; | A solution of 3-bromobenzene-1,2-diamine (2-21, 400 mg, 2.15 mmol) in HCOOH (5 mL) was stirred at 100 °C for 2 h. Upon reaction completion, the resulting mixture was concentrated under reduced pressure to provide intermediate 2-22 (yellow solid, 410 mg, 97percent yield). LCMS (m/z): 197 [M + HI . |
95% | for 2 h; Reflux | step 2: A mixture of 3-bromobenzene-l,2-diamine (1.5 g, 8 mmol) in formic acid (10 mL) was heated at reflux for 2 h. The reaction mixture was concentrated in vacuo. To the residue was added a satd. aq. solution of NaHC03 and mixture was extracted with EtOAc. The combined extracts was dried (MgSO i), filtered, and evaporated in vacuo to afford 4-bromo-lH-benzo[d]imidazole as a gray solid (1.5 g, 95percent). MS (ESI): m/z = 197 [M+l]+. |
94% | Stage #1: at 100℃; for 1 h; Stage #2: With sodium hydroxide In water |
Step 2: 4-Bromo-lH-benzimidazole; A solution of l,2-diamino-3-bromobenzene (2.00 g, 10.7 mmol) in formic acid (10 mL) was stirred at 1000C for 1 hour. The pΗ of the mixture was adjusted to 14 by the addition of 4 M sodium hydroxide solution, precipitating the product as a solid. This was separated by filtration, washed with water and air- dried affording the product as an off-white solid. A further crop of equally pure material precipitated from the filtrate upon standing at room temperature for a few days. Total yield = 1.98 g, 94percent. 1H NMR (500 MHz, ds-DMSO): δ 12.83 (1 H, s), 8.30 (1 H, s), 7.58 (1 H, d, J = 7.9 Hz), 7.41 (1 H, d, J = 7.1 Hz), 7.14 (1 H, t, J = 7.8 Hz); m/z (ES+) 197, 199 [MH+]. |
94% | Stage #1: at 100℃; for 1 h; |
Step 2: 4-Bromo-lH-benzimidazole; A solution of l,2-diamino-3-bromobenzene (2.00 g, 10.7 mmol) in formic acid (10 mL) was stirred at 1000C for 1 hour. The pΗ of the mixture was adjusted to 14 by the addition of 4M sodium hydroxide solution, precipitating the product as a solid. This was separated by filtration, washed with water and air- dried affording the product as an off-white solid. A further crop of equally pure material precipitated from the filtrate upon standing at room temperature for a few days. Total yield = 1.98 g, 94percent. 1H NMR (500 MHz, DMSO): δ 12.83 (1 H, s), 8.30 (1 H, s), 7.58 (1 H, d, J 7.9 Hz), 7.41 (1 H, d, J 7.1 Hz), 7.14 (1 H, t, J 7.8 Hz); m/z (ES+) 197, 199 [MH+]. |
83% | at 100℃; for 1 h; | A solution of 1,2-diamino-3-bromobenzene (750 mg, 4.0 mmol) in formic acid (4 mL) was heated at 100 °C for 1 h. The mixture was allowed to cool to room temperature, then was basified (pH - 14) by the addition of 4 N sodium hydroxide solution. The product 4-bromo-lH-benzimidazole precipitated as an off-white solid, and was separated by filtration, washed with water and dried in a drying pistol under vacuum at 50 °C (654 mg, 83percent). m/z (ES+) 197, 199 [MH]+. |
1.65 g | at 100℃; for 1 h; | A mixture of 3-bromobenzene-l,2-diamine (2 g, 10.7 mmol) in HCOOH was stirred at 100°C for 1 h. The mixture was cooled and concentrated in vacuo and diluted with ethyl acetate and aq. NaHC03. The mixture was extracted further with ethyl acetate and the combined organic layers dried and concentrated to give the crude product which was purified by column chromatography to obtain the desired product (1.65 g, Yield 80percent). LCMS (m/z): 197.0 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.9 g | With toluene-4-sulfonic acid In tetrahydrofuran at 60℃; for 0.333333 h; Inert atmosphere | To a stirring dark suspension of 3-bromo-l,2-benzenediamine (Combi-Blocks, Inc. 4.7 g, 25.1 mmol) and 4- methylbenzene sulfonic acid, monohydrate (0.048 g, 0.251 mmol) in THF (40 mL) at 20 °C under argon was added triethyl orthoformate (Sigma- Aldrich, St. Louis MO, 4.18 mL, 25.1 mmol) dropwise over a period of 5 min. The reaction was stirred for 10 min then heated to 60 °C for 20 min. The reaction was then cooled and concentrated under reduced pressure. The resulting dark solid was then triturated with diethyl ether (50 mL) and dried under reduced pressure to afford 4-bromo-lH-benzo[d]imidazole (4.9 g) as dark solid. |
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