Structure of 23058-81-3
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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. : | 23058-81-3 |
Formula : | C12H17Br |
M.W : | 241.17 |
SMILES Code : | CC(C1=CC(C(C)C)=CC(Br)=C1)C |
MDL No. : | MFCD12547791 |
Boiling Point : | No data available |
InChI Key : | VRKJTEHREIEDIE-UHFFFAOYSA-N |
Pubchem ID : | 11630091 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.5 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 63.3 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.34 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.87 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.7 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.81 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.5 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.44 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.61 |
Solubility | 0.00588 mg/ml ; 0.0000244 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.6 |
Solubility | 0.00599 mg/ml ; 0.0000248 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.9 |
Solubility | 0.00302 mg/ml ; 0.0000125 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 |
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) |
No |
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) |
Yes |
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 |
-4.31 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 |
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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.67 |
* 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 |
---|---|---|
62% | To a mixture of 4-bromo-2,6-bis(propan-2-yl)aniline (20.5 g, 80.02 mmol, 1.00 equiv) in 2N hydrochloric acid (210 mL) at -5° C. was added NaNO2 (13.8 g, 200.00 mmol, 2.50 equiv) in portions. The reaction was allowed stir at -5° C. for 10 min. Hypophosphorous acid (90 mL) was then added at -5° C. The reaction was warmed to room temperature and then stirred for 12 h. The resulting solution was extracted with 300 mL of ethyl acetate. The organic layer was concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:100) to give 12 g (62percent) of 1-bromo-3,5-bis(propan-2-yl)benzene as a light brown oil. 1H NMR (300 MHz, CDCl3): delta 7.18 (s, 2H), 6.98 (s, 1H), 2.89-2.80 (m, 2H), 1.23 (d, J=6.9 Hz, 12H) ppm. | |
52% | 138 ml (2.59 mol) of96percent sulfuric acid was added dropwise to a solution of <strong>[80058-84-0]4-bromo-2,6-diisopropylaniline</strong> (as prepared above, purity ca. 90percent) in 2000 ml of95percent ethanol cooled to -1 ooc at such a rate to keep the reaction temperature below 7°C. After the addition was complete, the formed solution was stirred at roomtemperature for 1 h. Then, the reaction mixture was cooled in an ice-bath, and asolution of 103.1 g (1.49 mol) of sodium nitrite in 215 ml of water was addeddropwise over ca. 1 h. The formed solution was stirred at the same temperature for30 min. Further on, the cooling bath was removed, and 18 g of copper powder was added. Upon completion of the rapid evolution of nitrogen additional portions (ca. 5g each, ca. 70 gin total) of copper powder were added with 10 min intervals untilgas evolution ceased completely. The reaction mixture was stirred at roomtemperature overnight, then filtered through glass frit (G3), diluted with two-foldvolume of water, and crude product was extracted with 4 x 200 ml of dichloromethane. The combined extract was dried over K2C03, evaporated todryness, and then distilled in vacuum (b.p. up to 120°C/5 mm Hg) to give ayellowish liquid. This product was additionally purified by flash-chromatography onsilica gel 60 ( 40-63 )lm; eluent: hexane) and distilled once again (b.p. 85-99°C/5mm Hg) to give 120.0 g (52percent) of 1-bromo-3,5-diisopropylbenzene as a colorless liquid.1H NMR (CDCh): b 7.19 (d, J = 1.2 Hz, 2H), 6.99 (br.t, 1H), 2.86 (sept, J = 6.9 Hz,2H), 1.24 (d, J= 6.9 Hz, 12H). 13CeH} NMR (CDCh): b 151.04, 126.85, 123.70,122.34, 34.06, 23.87 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Production Example 5 1,2-Bis(bis(3,5-diisopropylphenyl)phosphino)benzene 3,5-Diisopropylbromobenzene (3.04 g, 12.60 mmol) was added dropwise to magnesium (0.48 g, 19.75 mmol) and THF (7 mL) in an argon atmosphere. After the dropwise addition, the mixture was heated under reflux for 1 hour. The reaction mixture was cooled to ambient temperature and filtered, and the thus-obtained THF solution of 3,5-diisopropylphenylmagnesium bromide, and 1,2-bis(dichlorophosphino)benzene (0.45 g, 1.61 mmol) were reacted as in Production Example 1. The reaction was allowed to proceed overnight at 60 C. After purification, the title compound was obtained as a yellow oily substance (1.18 g, yield 74%). 1H NMR (CDCl3) δ 1.11 (s, 24H), 1.14 (s, 24H), 2.69-2.79 (m, 8H), 6.86-6.89 (m, 8H), 6.94 (brs, 12H), 7.01-7.09 (m, 2H), 7.22-7.26 (m, 2H); 13C NMR (CDCl3) δ 23.9 (8C), 24.0 (8C), 34.0 (8C), 124.4 (4C), 128.6 (2C), 129.4 (dd, J=9.9 Hz, 8C), 133.8 (t, J=2.8, 2.9 Hz, 2C), 137.5 (dd, J=2.9 Hz, 4C), 144.6 (dd, J=10.2, 10.3 Hz, 2C), 148.2 (dd, J=3.2, 3.4 Hz, 8C); 31P NMR (CDCl3) δ -12.8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.9 g | To the solution of <strong>[23058-81-3]3,5-diisopropylbromobenzene</strong>(5.76 g, 23.9 mmol) and tetramethylethylenediamine(3.6 mL, 23.9 mmol) in diethyl ether(30 mL), solution of n-butyllithium in n-hexane(14.5 mL, 23.9 mmol) was dropped at -60C. Reaction solution was stirred for 1.5 hours at -60C, and further was stirred for 30 minutes at 0C, then, solution of triisopropyl borate (6.6 mL) in diethyl ether(5 mL) was dropped at -60C. Reaction solution was stirred for 30 minutes at -60C, and further, was stirred overnight at room temperature, then, diluted hydrochloric acid (50 mL) was added. Resulting solid part was filtered to obtain the crude product of 3,5-diisopropylphenylboronic acid (5.9 g). |
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