Cat.NO.:A227277 Purity:97%
Product Details of [ 101085-03-4 ]
CAS No. : | 101085-03-4 |
Formula : |
C8H7BrO3 |
M.W : |
231.04
|
SMILES Code : | O=C(OC)C1=CC=C(O)C=C1Br |
MDL No. : | MFCD18398783 |
InChI Key : | FDMYWFGQALCJRU-UHFFFAOYSA-N |
Pubchem ID : | 69974803 |
Safety of [ 101085-03-4 ]
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Computational Chemistry of [ 101085-03-4 ] Show Less
Physicochemical Properties
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 47.44 |
TPSA ?
Topological Polar Surface Area: Calculated from |
46.53 Ų |
Lipophilicity
Log Po/w (iLOGP)?
iLOGP: in-house physics-based method implemented from |
1.85 |
Log Po/w (XLOGP3)?
XLOGP3: Atomistic and knowledge-based method calculated by |
2.14 |
Log Po/w (WLOGP)?
WLOGP: Atomistic method implemented from |
1.94 |
Log Po/w (MLOGP)?
MLOGP: Topological method implemented from |
2.06 |
Log Po/w (SILICOS-IT)?
SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.89 |
Consensus Log Po/w?
Consensus Log Po/w: Average of all five predictions |
1.98 |
Water Solubility
Log S (ESOL):?
ESOL: Topological method implemented from |
-2.86 |
Solubility | 0.32 mg/ml ; 0.00138 mol/l |
Class?
Solubility class: Log S scale |
Soluble |
Log S (Ali)?
Ali: Topological method implemented from |
-2.75 |
Solubility | 0.412 mg/ml ; 0.00178 mol/l |
Class?
Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)?
SILICOS-IT: Fragmental method calculated by |
-2.76 |
Solubility | 0.403 mg/ml ; 0.00175 mol/l |
Class?
Solubility class: Log S scale |
Soluble |
Pharmacokinetics
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) |
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) |
No |
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 |
-6.19 cm/s |
Druglikeness
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 |
0.0 |
Bioavailability Score?
Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
Medicinal Chemistry
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) |
1.53 |
Application In Synthesis of [ 101085-03-4 ]
* 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.
- Downstream synthetic route of [ 101085-03-4 ]
[ 101085-03-4 ] Synthesis Path-Downstream 1~2
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41.1% | With sulfuric acid; sodium nitrite; In water; ethyl acetate; | Finally, a solution of sulfuric acid (98%, 6 mL) in H2O (75 mL) was added to <strong>[98545-64-3]methyl 4-amino-2-bromobenzoate</strong> (1.23 g, 5.38 mmol) and the resulting suspension was heated to 90 C., then stirred for 5 h at this temperature. The reaction mixture was cooled to 0 C. and a solution of NaNO2 (384 mg, 5.57 mmol) in H2O (5 mL) was added dropwise, then the reaction was allowed to warm to ambient temperature. The reaction mixture was then added to a solution of sulfuric acid (98%, 6 mL) in H2O (75 mL) that had been preheated to 90 C. The reaction mixture was stirred at 90 C. for 1 h, and then allowed to cool. The reaction mixture was partitioned between EtOAc (200 mL) and aqueous solution. The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (35% EtOAc in hexanes) to afford compound 10 in 41.1% (508 mg) yield as a light brown solid. 1H-NMR (CDCl3, 400 MHz) delta 7.76 (1H, d, J=8.8 Hz, Ar), 7.09 (1H, s, Ar), 6.75 (1H, d, J=8.8 Hz, Ar), 3.84 (3H, s, OCH3); 13C-NMR (CDCl3, 100 MHz) delta 166.2, 160.3, 133.5, 123.4, 122.1, 121.4, 114.3, 52.1; MS (ESI) m/z Calcd for C8H7BrO3 (M+): 230.0, Found: 231.0 (M+H+). |
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