Structure of 95970-08-4
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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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CAS No. : | 95970-08-4 |
Formula : | C7H6Br2O |
M.W : | 265.93 |
SMILES Code : | COC1=CC(Br)=CC=C1Br |
MDL No. : | MFCD07780698 |
InChI Key : | YJGNTPRGNRICPY-UHFFFAOYSA-N |
Pubchem ID : | 13399557 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 48.33 |
TPSA ? Topological Polar Surface Area: Calculated from |
9.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.59 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.56 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.22 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.3 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.18 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.97 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.48 |
Solubility | 0.0881 mg/ml ; 0.000331 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.4 |
Solubility | 1.05 mg/ml ; 0.00397 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.23 |
Solubility | 0.0156 mg/ml ; 0.0000587 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 |
-6.1 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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.62 |
* 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 |
---|---|---|
81% | Stage #1: With sulfuric acid; sodium nitrite In water at 12℃; Stage #2: With hydrogen bromide; copper(I) bromide In water at 40 - 65℃; |
adding 1020 g of 2-bromo-5-aminoanisole to the reaction vessel,Add about 30percent sulfuric acid 8380 g and stir.Then, a solution of 455 g of sodium nitrite and 1000 g of water was added dropwise, and the process temperature was controlled at about 12 °C.After the addition is completed, the mixture is stirred for a while to prepare a diazonium salt for use. Add 520 g of cuprous bromide and HBr 1350 g to another reaction flask.The above diazonium salt is added under stirring, and the temperature rises when decomposed, and the controlled temperature is 40 to 65 °C.After the addition, continue to stir, keep the reaction for a period of time, stir, cool, filter,The brown solid 2,5-dibromoanisole was obtained in an amount of 1086 g, and the content was more than 97percent, and the yield was 81percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at 20 - 70℃; | Preparation 111; 1 ,4-Dibromo-2-methoxy-benzene; Add dropwise potassium tert-butoxide (118.2 ml, 118.2 mmol, 1 M in hexane) to a solution of l,4-dibromo-2-fluorobenzene (25.0 g, 98.5 mmol) in THF (492 mL) and MeOH (40 mL, 984.7 mmol) at RT. Heat the mixture at 70 0C overnight. Quench the mixture with water (50 mL), dilute with Et2O (400 mL), wash once with saturated NH4Cl (300 mL) and back extract the aqueous with Et2O (200 mL). Dry the combined organic phase over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatograph, eluting with 5-10percent ethylacetate/hexane to give 22.0 g (84percent) of the title compound. GC m/z (79Br81Br) 266 [M]+. |