Structure of 3001-15-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 3001-15-8 |
Formula : | C12H8I2 |
M.W : | 406.00 |
SMILES Code : | IC1=CC=C(C2=CC=C(I)C=C2)C=C1 |
MDL No. : | MFCD00001057 |
InChI Key : | GPYDMVZCPRONLW-UHFFFAOYSA-N |
Pubchem ID : | 76348 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 77.31 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.98 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
5.66 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.56 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
5.45 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
5.45 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.82 |
Log S (ESOL):? ESOL: Topological method implemented from |
-6.49 |
Solubility | 0.000131 mg/ml ; 0.000000323 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.42 |
Solubility | 0.00153 mg/ml ; 0.00000376 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-6.73 |
Solubility | 0.0000756 mg/ml ; 0.000000186 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-4.76 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.04 |
* 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 |
---|---|---|
With copper; potassium carbonate;PEG-6000; In 1,2-dichloro-benzene; for 22h;Heating / reflux; | (Synthetic Example 1) N,N'-diphenyl-N,N'-bis(3-tolyl)-4,4'-diaminobiphenyl (3,3-TPD) was synthesized as follows. 1.0g (2.46mmol) of 4,4'-diiodobiphenyl and 20 ml of o-dichlorobenzene were added to a 100 ml four-necked flask made of glass. Furthermore 1.08g (5.90mmol) of m-methyldiphenylamine, 0.104g of poly(ethylene glycol) PEG-6000 as a reaction accelerator that was available from Wako Pure Chemical Industries, Ltd., 2.73g (0.0198mol) of potassium carbonate and 0.635g (9.87mmol) of powdered copper were added thereto. It was determined for tracing by the high-speed liquid chromatography. And it was stirred and refluxed for 22 hours until no peaks of starting materials and intermediates were determined. It was filtrated at the hot temperature. The product was washed with dichloromethane until color of the filtrate was to be light. The solvent was distilled under reduced pressure. Residual product was purified by silica gel column chromatography to obtain 3,3-TPD that is represented by Compound Example 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; copper(II) sulfate; In tridecane; at 230℃; for 24h; | (Compound 1): In a 50 milliliter round bottom flask there were added 4,4'-diiodo-1,1'-biphenyl (2.1 grams), 3,6-diphenyl carbazole (3.3 grams), potassium carbonate powder (1.4 grams), copper sulfate pentahydrate (0.06 grams), and 5 milliliters of tridecane.. The resulting mixture was heated to 230° C. and stirred at this temperature under argon for 24 hours.. After cooling to room temperature (~23° C.), the solids content resulting was ground into slurry, which slurry was then transferred to a filtration funnel, washed with hexane to remove the tridecane, followed by washing with 3 percent hydrochloric acid and water.. The solid resulting was then dissolved in hot toluene.. The insoluble residue was filtered hot.. After cooling to room temperature, the product was crystallized from the solution to yield 2.3 grams of 4,4'-bis-[9-(3,6-diphenylcarbazolyl)]-1,1'-biphenyl as a yellowish powder.. This compound had a melting point of 294° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(Synthetic Example 3) The mixture of 3,3-TPD, 4,4-TPD and N,N'-diphenyl-N-(3-tolyl)-N'-(4-tolyl)-4,4'-diaminobiphenyl (3,4-TPD) that is represented by Compound Example 3 was synthesized as follows. Mixture of 438g (2.43mol) of 3-methyldiphenylamine and 49g (0.27mol) of 4-methyldiphenylamine whose mol ratio is 90: 10 were added to a 5000 ml four-necked flask made of glass. Further 28g (4.4mol) of powdered copper was added thereto. It was heated at 30 degrees Centigrade. 450g (1.1mol) of 4,4'-diiodobiphenyl and 47g of poly(ethylene glycol) PEG-6000 that was available from Wako Pure Chemical Industries, Ltd. were added thereto. It was heated at 100 degrees Centigrade, and then 307g (2.2mol) of powdered potassium carbonate was added thereto. It was heated at 205 degrees Centigrade, and stirred for 14 hours. After cooling, DMF was added thereto, and stirred at 130 degrees Centigrade for 1 hour. After cooling till 90 degrees Centigrade, hot water was added thereto. It was stirred for 2 hours. After filtration, filtrated cake was washed with hot water to obtain brown solid. The obtained brown solid was dispersed and stirred into DMF for 1 hour, filtrated and washed with DMF and methanol. The obtained solid was refluxed with activated carbon in xylene for 1 hour. After cooling till 70 degrees Centigrade, it was filtrated. The filtrate was passed through a column packing adsorbent to obtain colorless solution. The solvent was distilled under reduced pressure. Precipitated crystals were filtrated out and dried to obtain 455g of mixture of TPD. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE II Synthesis of 4,4'-Bis-[9-(3,6-diphenylcarbazolyl)]-1-1,1'-biphenyl In a 50 milliliter round bottom flask there were added 4,4'-diiodo-1,1'-biphenyl (2.1 grams), 3,6-diphenyl carbazole (3.3 grams), potassium carbonate powder (1.4 grams), copper sulfate pentahydrate (0.06 grams), and 5 milliliters of tridecane. The resulting mixture was heated to 230° C. and stirred at this temperature under argon for 24 hours. After cooling to room temperature (~23° C.), the solids content resulting was ground into slurry, which slurry was then transferred to a filtration funnel, washed with hexane to remove the tridecane, followed by washing with 3 percent hydrochloric acid and water. The solid resulting was then dissolved in hot toluene. The insoluble residue was filtered hot. After cooling to room temperature, the product was crystallized from the solution to yield 2.3 grams of 4,4'-bis-[9-(3,6-diphenylcarbazolyl)]-1,1'-biphenyl as a yellowish powder. This compound had a melting point of 294° C. Its chemical structure was confirmed by proton analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; | EXAMPLE V Preparation of N,N'-diphenyl-N,N'-bis-(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine in the absence of the aliphatic hydrocarbon solvent. A 500 milliliter 3 necked round bottom flask equipped with an argon purge, a condenser and an overhead mechanical stirrer was charged with 81.2 grams (0.2 mole) of 4,4'-diiodobiphenyl, 146.4 grams (0.8 mole) of 3-methyl-diphenylamine, 89.6 grams (1.6 moles) of KOH flake and 80 grams (1.0 mole) of copper powder. The flask was immersed in a 165° C. oil bath and the two-phase melt was stirred for 3 hours. Hot (140° C.) Soltrol.(R). 170 was added and the inorganic solid separated by vacuum filtration. On cooling, the product crystallized from the filtrate and was isolated in 89percent yield by filtration. Purification was accomplished by slurrying the product with neutral alumina (10 grams) in 1 liter of Soltrol.(R). 170 at 150° C. for six hours, the alumina was removed by filtration and the purified product crystallized from the filtration on cooling. Isolation by filtration was accomplished with a 95percent recovery of the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 24h; | General procedure: CuI (0.05 equiv), 1,10-phenanthroline (0.1 equiv) and K2CO3 (2 equiv) were placed in an oven-dried screw-capped test tube with Teflon-lined septum that was filled with nitrogen. About 2.5 mL of dry DMF was then added at room temperature. Now the corresponding aryl iodide (1.0 mmol) was added followed by MBI or FMBI (1.0 equiv) and the tube was placed in the preheated oil bath at 140 C and the reaction mixture was magnetically stirred for 22 h. After complete disappearance of iodobenzene (the progress of the reaction was followed by TLC), the reaction mixture was allowed to cool to room temperature. Then water was added and the reaction mixture was extracted with ethyl acetate. After removal of the solvent in vacuum, the crude residue was purified by column chromatography.5- (or 6-) (Difluoromethoxy)-2-(phenylsulfanyl)-1H-benzimidazole (1). |
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