Structure of 4028-63-1
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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. : | 4028-63-1 |
Formula : | C9H11I |
M.W : | 246.09 |
SMILES Code : | CC1=C(I)C(C)=CC(C)=C1 |
MDL No. : | MFCD00013707 |
InChI Key : | GTPNXFKONRIHRW-UHFFFAOYSA-N |
Pubchem ID : | 77647 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 54.06 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.62 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.39 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.22 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.12 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.19 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.71 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.58 |
Solubility | 0.00654 mg/ml ; 0.0000266 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.11 |
Solubility | 0.0192 mg/ml ; 0.0000782 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.51 |
Solubility | 0.00752 mg/ml ; 0.0000305 mol/l |
Class? Solubility class: Log S scale |
Moderately 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 |
Yes |
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) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
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 |
-4.68 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
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 |
1.0 |
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) |
1.76 |
* 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 |
---|---|---|
11%; 74% | General procedure: 4-Iodoanisole (1mmol), TMSA (1.1mmol) and K2CO3 (2mmol) were added to a freshly prepared solution of PdNPs (5mL) in a 25mL round bottomed flask fitted with stopper. Then, the reaction mixture was stirred at 40C. The reaction progress was monitored by TLC, until complete consumption of aryl iodide. To the reaction mixture containing in situ formed 4-ethynylanisole the next batch of aryliodide (1mmol) was added and the reaction mixture was further allowed to stir until complete consumption of the arylacetylene. In this manner the targeted unsymmetrical diarylacetylene was formed. The detailed procedure is provided in the Supp. Info. Detailed procedure for synthesis of symmetrical diarylacetylenes is also mentioned in SI. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In methanol; acetonitrile; at 45℃; | General procedure: 4-Iodoanisole (1mmol), TMSA (1.1mmol) and K2CO3 (2mmol) were added to a freshly prepared solution of PdNPs (5mL) in a 25mL round bottomed flask fitted with stopper. Then, the reaction mixture was stirred at 40C. The reaction progress was monitored by TLC, until complete consumption of aryl iodide. To the reaction mixture containing in situ formed 4-ethynylanisole the next batch of aryliodide (1mmol) was added and the reaction mixture was further allowed to stir until complete consumption of the arylacetylene. In this manner the targeted unsymmetrical diarylacetylene was formed. The detailed procedure is provided in the Supp. Info. Detailed procedure for synthesis of symmetrical diarylacetylenes is also mentioned in SI. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With selenium; caesium carbonate; copper dichloride; In N,N-dimethyl-formamide; at 20 - 140℃; for 24h;Inert atmosphere; | In room temperature,2,4,6-trimethyliodobenzene (1.2 mmol, 3 equiv), elemental selenium (1.2 mmol, 3 equiv), <strong>[1006-68-4]5-phenyl-1,3-oxazole</strong> (0.4 mmol, 1 equiv), Copper chloride (0.04 mmol), cesium carbonate (1.2 mmol, 3 equiv) was added to the reaction tube, then filled with nitrogen, and replaced three times. Under a nitrogen reaction, 2 mL of N,N-dimethylformamide was added. The solvent was stirred at a reaction temperature of 140 C for 24 h. After monitoring the reaction by thin layer chromatography, the reaction mixture was cooled, then diluted with ethyl acetate, and the diluted solution was transferred to a separating funnel, and extracted with saturated brine to separate the aqueous and organic phases, and then acetic acid. The aqueous phase was extracted three times with ethyl acetate. The organic phase was combined, 5 g anhydrous sodium sulfate was added, and the mixture was allowed to stand for 30 min, and the filter cake was washed three times with 5 mL of ethyl acetate each time, then the solvent was spun off, and the product was isolated by column chromatography. Detachment: petroleum ether: ether = 98:2), the product was a yellow solid.The melting point was 65-66 C, the yield was 51%, and the weight of the product was 70 mg. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With selenium; potassium phosphate; copper(l) chloride; In N,N-dimethyl-formamide; at 140℃; for 24h;Inert atmosphere; | In room temperature, 2,4,6-trimethyliodobenzene (12 mmol, 3 equiv), elemental selenium (12 mmol, 3 equiv), ethyl 1,3-oxazol-5-carboxylate (4 mmol, 1 equiv), copper chloride (0.4 mmol) and potassium phosphate (12 mmol, 3 equiv) were added to the reaction tube, then filled with nitrogen, and replaced three times. In a nitrogen reaction environment, then 20 mL of N,N-dimethylformamide reaction solvent was added. Stir at a reaction temperature of 140 C for 24 h. After monitoring the reaction by thin layer chromatography, the reaction mixture was cooled. Then, ethyl acetate was added for dilution, and the diluted solution was transferred to a separatory funnel and extracted with saturated brine. The aqueous phase and the organic phase were separated, and the aqueous phase was extracted three times with ethyl acetate. The organic phases were combined, 25 g of anhydrous sodium sulfate was added, and the mixture was stood still for 30 min. Wash the filter cake 3 times with 50 mL of ethyl acetate each time. Then spin off the solvent, the product was isolated by column chromatography (eluent: petroleum ether: diethyl ether = 98:2), yield 77%, product weight: 1.044 g. |
A125861 [866996-02-3]
4-Ethyl-1-iodo-2-methylbenzene
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