Structure of 56990-02-4
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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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Search for reports by entering the product batch number.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 56990-02-4 |
Formula : | C7H4Br2O |
M.W : | 263.91 |
SMILES Code : | O=CC1=CC(Br)=CC(Br)=C1 |
MDL No. : | MFCD00156887 |
InChI Key : | ZLDMZIXUGCGKMB-UHFFFAOYSA-N |
Pubchem ID : | 622077 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 47.23 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.02 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.55 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.02 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.94 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.34 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.97 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.09 |
Solubility | 0.0214 mg/ml ; 0.0000811 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.59 |
Solubility | 0.0673 mg/ml ; 0.000255 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.05 |
Solubility | 0.0234 mg/ml ; 0.0000887 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
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 |
-5.39 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.37 |
* 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 |
---|---|---|
84% | With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 1h; | Example 15 [4-[3,5-Bis-[(4-trifluoromethylphenyl)ethynyl]benzyloxy]-2-methylphenoxy]acetic acid 3,5-Dibromobenzaldehyde (1.7 g, 6.3 mmol) was dissolved in methanol (100 mL) and sodium borohydride (0.250 g, 6.3 mmol) was added at 0° C. The reaction mixture was stirred for 0.5 h at 0° C. and then at 20° C. for another 0.5 h. The reaction mixture was concentrated in vacuo, diluted with brine (250 mL), acidified with hydrochloric acid and extracted with dichloromethane (3*50 mL). Evaporation of the organic solution gave 3,5-dibromo-benzyl alcohol as a white crystalline compound. Yield: 1.4 g (84percent). RF (SiO2, hexanes/ethyl acetate 9:1) 0.25. 1H NMR spectrum (300 MHz, CDCl3, A) 7.59 (d, J=1.5 Hz, 1H); 7.47 (d, J=1.5 Hz, 2H); 4.36 (s, 2H); 1.55 (s, 1H). |
84% | With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 1h; | Example 15; [4-[3,5-Bis-[(4-trifluoromethylphenyl)ethynyl]benzyloxy]-2-methylphenoxy]acetic acid; 3,5-Dibromobenzaldehyde (1.7 g, 6.3 mmol) was dissolved in methanol (100 mL) and sodium borohydride (0.250 g, 6.3 mmol) was added at 0 °C. The reaction mixture was stirred for 0.5 h at 0 °C and then at 20 °C for another 0.5 h. The reaction mixture was con- centrated in vacuo, diluted with brine (250 mL), acidified with hydrochloric acid and extracted with dichloromethane (3 x 50 mL). Evaporation of the organic solution gave 3,5-dibromo- benzyl alcohol as a white crystalline compound. Yield: 1.4 g (84 percent). RF (Si02, hexanes/ethyl acetate 9:1) 0.25. 1H NMR spectrum (300 MHz, CDCl3, No.H) : 7.59 (d, J=1.5 Hz, 1 H) ; 7.47 (d, J=1.5 Hz, 2 H); 4.36 (s, 2 H); 1.55 (s, 1 H). |
With sodium borohydrid; In methanol; | PREPARATION 9 3,5-Dibromobenzyl alcohol Sodium borohydride (0.75 g) was added portionwise to a stirred suspension of 3,5-dibromobenzaldehyde (10.46 g) in methanol (50 ml) at 0° C. The mixture was stirred at 0° C. for 30 minutes, allowed to warm to room temperature and then its pH was adjusted to 2 using concentrated hydrochloric acid. Evaporation under vacuum provided a residue which was partitioned between ethyl acetate and water. The organic phase was washed with water, dried (MgSO4), then evaporated under vacuum to furnish the title compound as a solid (10.0 g), m.p. 103°-104° C. Found: C,31.98; H,2.23. C7 H6 Br2 O requires C,31.61; H,2.77percent. |
Example 1.1.76: (3-isopropyl-5-(methylsulfonylmethyl)phenyl)methanamine; To stirring solution of 5.0 g (18.9 mmol) of 3,5-dibromobenzaldehyde in 30 mL of MeOH and 25 mL of THF at 0 0C was added 819 mg of NaBH4 in 3 portions. The yellow solution was stirred at 0 0C for 30 min. and then concentrated. Water and EtOAc were added, and 1 N HCl was added to a pH = 7. The organic layer was washed with 25 mL of brine, dried over Na2SO4, filtered, and concentrated. (3,5-dibromophenyl)methanol was used in the next reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; copper(l) cyanide; In DMF (N,N-dimethyl-formamide); at 140℃; | A mixture of 3, [5-DIBROMOBENZALDEHYDE] (1 [G),] copper cyanide (0.331 [G)] and pyridine (0.3 mL) in DMF (30 mL) was heated to [140C] overnight. The solution was allowed to cool to r. t. and dropped into water (30 [ML),] then exctracted with Et20 (15 mL). The organic phase was dried, concentrated in vacuo and the residue was purified by flash chromatography (CH, [CH/ACOET FROM] 95: 5 to 80: 20) to give the title compound (64 mg) as a yellow oil. T. I. c.: CH/AcOEt [8] : 2, Rf=0.52 (detection with 2, [4-DINITROPHENYLHYDRAZINE).] NMR [(CDCI3)] : [6] (ppm) 10.0 (s, [1H)] ; 8.20 (s, [1H)] ; 8.10 (s, [1H)] ; 8.00 (s, [1H).] [IR (NUJOL, CM~1)] : 2235.70 [(C--N)] ; 1700.14 [(C=O).] |