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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
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Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Structure of 90868-92-1
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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.
4.5
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CAS No. : | 90868-92-1 |
Formula : | C10H12BrN |
M.W : | 226.11 |
SMILES Code : | NC(C1=CC=C(Br)C=C1)C2CC2 |
MDL No. : | MFCD05192037 |
InChI Key : | CFTNYXDVHSKCKL-UHFFFAOYSA-N |
Pubchem ID : | 3948276 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H314-H335 |
Precautionary Statements: | P260-P264-P270-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P403+P233-P405-P501 |
Class: | 8 |
UN#: | 2735 |
Packing Group: | Ⅱ |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.4 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 54.12 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.02 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.4 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.25 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.47 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.8 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.87 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.56 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.9 |
Solubility | 0.286 mg/ml ; 0.00127 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.43 |
Solubility | 0.835 mg/ml ; 0.00369 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.55 |
Solubility | 0.0643 mg/ml ; 0.000284 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
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 |
-6.08 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 |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.78 |
* 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 |
---|---|---|
72% | A solution of 4-bromo-benzonitrile (6.30 g) in tetrahydrofuran (50 ml.) was added over a period of 20 min to a 0.5 M solution of cyclopropylmagnesium bromide in tetrahydrofuran (200 ml.) chilled in an ice bath. After stirring the resulting solution with cooling for 5.5 h, methanol (100 ml_) was added over a period of 20 min. Then sodium borohydride (2.65 g) was added portionwise and the resulting mixture was warmed to room temperature overnight. Aqueous saturated NaHCO3 solution was added and then the pH value of the mixture was adjusted to 8-9 using 1 M hydrochloric acid. The resulting mixture was extracted with dichloromethane and the combined extracts were washed with water and dried (MgSO4). The solvent was evaporated to leave an oil that was dissolved in dichloromethane. The resulting solution was extracted with 1 M hydrochloric acid and the combined aqueous extracts were basified (pH value ca. 8-9) with 4 M aqueous NaOH solution. The aqueous solution was extracted with dichloromethane and the combined organic extracts were washed with water and dried (MgSO4). The solvent was evaporated to afford the title compound as an oil. Yield: 5.56 g (72% of theory); Mass spectrum (ESI+): m/z = 209/211 (Br) [M+H-NH3]+. | |
A solution of 4-bromobenzonitrile (1.30 g, 7.14 mmol) in anhydrous tetrahydrofuran (5 mL) was added over a period of 15 mins to a 0.5 M solution of bromo(cyclopropyl)magnesium (42 mL) in anhydrous tetrahydrofuran chilled in an ice bath. After stirring the resulting solution at 0 C for 5.5 hours, anhydrous methanol (20 mL) was added over a period of 15 mins. Then sodium borohydride (540 mg, 14.2 mmol) was added in portions and the resulting mixture was warmed to rt and stirred for 14 hours. On completion, the reaction mixture was concentrated in vacuo. The residue was diluted with saturated sodium bicarbonate solution (30 mL) and extracted with dichloromethane (3 X 30 mL). The combined organic layers were extracted with 1 M hydrochloric acid (2 X 30 mL), then the aqueous phase was collected and basified with 4 M aqueous sodium hydroxide solution until pH = 89. The aqueous phase was again extracted with dichloromethane (3 X 30 mL), and the combined organic layers were dried with anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound. ?H NIVIR (4001V11{z, CDC13) = 7.47 (d, J8.4 Hz, 2H), 7.31 (d, J 8.4 Hz, 2H), 3.19 (d, J 8.5 Hz, 1H), 1.68 (s, 2H), 1.11 - 1.00 (m,1H), 0.67-0.58 (m, 1H), 0.53 -0.45 (m, 1H), 0.38 -0.31 (m, 1H), 0.31 -0.24 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydrogencarbonate; In dichloromethane; water; at 20℃; for 0.5h;Cooling with ice bath; | Triphosgene (1.31 g) was added at once to a vigorously stirred mixture ofNaHCO3 (2.14 g) in water (50 ml.) and <strong>[90868-92-1](4-bromo-phenyl)-cyclopropyl-methylamine</strong> (2.50 g) in dichloromethane (50 ml.) chilled in an ice bath. The cooling bath was removed and the mixture was stirred at room temperature for another 30 min. Then the organic phase was separated and dried (MgSO4) and the solvent was evaporated to afford the isocyanate as an oil that was directly submitted to the next reaction step. Yield: 2.88 g (quantitative); Mass spectrum (ESI ): m/z = 250/252 (Br) [M-H]". |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; at 20℃; for 16h; | Production Example 29; To a mixture of <strong>[90868-92-1]1-(4-bromophenyl)-1-cyclopropylmethane amine</strong> (1.08 g) and THF (10 mL) were added triethylamine (1 mL) and di-tert-butyl dicarbonate (1.25 mL), and the mixture was stirred at room temperature for 16 hours. The solvent was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl [(4-bromophenyl)(cyclopropyl)methyl]carbamate (1.36 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; triethylamine; In ethanol; at 80℃; for 16h;Inert atmosphere; | To a solution of (4-bromophenyl)-cyclopropyl-methanamine (900 mg, 3.98 mmol) in ethanol (40 mL) was added Pd(dppf)C12DCM (582 mg, 796 umol) and triethylamine (2.01 g, 19.9 mmol) under nitrogen gas. The suspension was degassed under vacuum and purged with carbon monoxide several times. The mixture was stirred under carbon monoxide (50 psi) at 80 C for 16 hours. On completion, the reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (5i02, dichloromethane:methanol = 50:1 to 20:1) to give the title compound. ?H NIVIR (400MHz, CDC13) = 7.96 (d, J 8.4 Hz, 2H), 7.54 (d, J 8.4 Hz, 2H), 4.30 (q, J 7.2 Hz, 2H), 3.55 (d, J 9.6 Hz, 1H), 1.43 - 1.35 (m, 1H), 1.30 (t, J 7.2 Hz, 3H), 0.63 - 0.50 (m, 3H), 0.32 - 0.21 (m, 1H). |
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