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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
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Structure of 4870-65-9
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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. : | 4870-65-9 |
Formula : | C8H7BrO2 |
M.W : | 215.04 |
SMILES Code : | C1=C(C(C(O)=O)Br)C=CC=C1 |
MDL No. : | MFCD00004206 |
InChI Key : | WAKFRZBXTKUFIW-UHFFFAOYSA-N |
Pubchem ID : | 97919 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H314 |
Precautionary Statements: | P261-P280-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅱ |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 45.86 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.42 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.28 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.88 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.14 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.91 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.93 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.88 |
Solubility | 0.283 mg/ml ; 0.00131 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.7 |
Solubility | 0.429 mg/ml ; 0.00199 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.68 |
Solubility | 0.451 mg/ml ; 0.0021 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) |
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 |
-5.99 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 |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
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) |
2.0 |
* 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 |
---|---|---|
97% | α-Bromophenylacetic acid (5.01 g, 23.2 mmol.) is dissolved in aniline (25 mL, 274 mmol) and the mixture reacted in a closed vessel under MW irradiation at 1200C for 5 min (LC-MS monitoring: complete conversion). Dichloromethane (DCM) (100 mL) is added to the reaction mixture and the resulting solid is filtered; 2M Na2CO3 (50 mL) is added to the solution, and the aqueous layer is washed with DCM (3x100 mL). The aqueous layer is acidified with 12N HCl (36 mL) and the title compound is recovered as racemic mixture by filtration (5.1 g, 97% yield, white solid). | |
97% | at 120℃; for 0.0833333h;microwave irradiation; | a-Bromophenylacetic acid (5.01 g, 23.2 mmol) was dissolved in aniline (25 ml, 274 mmol) and the mixture reacted in a closed vessel under microwave irradiation at 120C for 5 min (UPLC-MS monitoring: complete conversion). Dichloromethane (DCM) (100 ml) was added to the reaction mixture and the resulting solid was filtered; 2M Na2CO3 (50 ml) was added to the solution, and the aqueous layer was washed with DCM (3x100 ml). The aqueous layer was acidified with 12N HC1 (36 ml) and the title compound was recovered as racemic mixture by filtration (5.1 g, 97% yield). |
97% | at 120℃; for 0.0833333h;microwave irradiation; | a-Bromophenylacetic acid (5.01 g, 23.2 mmol.) was dissolved in aniline (25 ml, 274 mmol) and the mixture reacted in a closed vessel under microwave irradiation at 120C for 5 min (UPLC-MS monitoring: complete conversion). Dichloromethane (DCM) (100 ml) was added to the reaction mixture and the resulting solid was filtered; 2M Na2CO3 (50 ml) was added to the solution, and the aqueous layer was washed with DCM (3x100 ml). The aqueous layer was acidified with 12N HC1 (36 ml) and the title compound was recovered as racemic mixture by filtration (5.1 g, 97% yield). |
24% | In neat (no solvent); at 100℃; for 72h; | 2-bromophenylacetic acid (2.15 g, 10.0 mmol) andaniline (4.09 g, 44.0 mmol) were heated at 100 C. for 72hours in the absence of a solvent the absence of a solvent.[0251] After cooling, the reaction mixture was dilutedwith ethyl acetate and extracted with 5% sodium hydroxide. The obtained aqueous phase was adjusted to a pHof 4 with IN hydrochloric acid and extracted with ethylacetate. The organic phase was dried over magnesiumsulfate and concentrated under reduced pressure The obtained crude product was recrystallized withwater-ethanol, thereby obtaining 560 mg (24.0%) of thetarget product 1H-NMR (acetone-d6)o: 2.02 (lH, bs), 5.15 (lH,s), 6.57 (lH, t, J=7.3 Hz), 6.67 (2H, d, J=8.8 Hz), 7.03 (2H,t, J=8.2 Hz), 7.27 (lH, t, J=7.3 Hz), 7.34(2H, t, J=8.1 Hz),7.55 (2H, d, J=7.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium carbonate; In aniline; | Preparation of 2-phenyl-2-(phenylamino)acetic acid (I1) α-Bromophenylacetic acid (5.01 g, 23.2 mmol) was dissolved in aniline (25 ml, 274 mmol), and the mixture reacted in a closed vessel under microwave irradiation at 120 C. for 5 minutes (UPLC-MS monitoring: complete conversion). Dichloromethane (DCM) (100 ml) was added to the reaction mixture, and the resulting solid was filtered; 2M Na2CO3 (50 ml) was added to the solution, and the aqueous layer was washed with DCM (3*100 ml). The aqueous layer was acidified with 12N HCl (36 ml) and the title compound was recovered as racemic mixture by filtration (5.1 g, 97% yield). |
97% | With sodium carbonate; In aniline; | Preparation of 2-phenyl-2-(phenylamino)acetic acid (I1) α-Bromophenylacetic acid (5.01 g, 23.2 mmol) was dissolved in aniline (25 ml, 274 mmol), and the mixture was reacted in a closed vessel under microwave irradiation at 120 C. for 5 minutes (UPLC-MS monitoring: complete conversion). Dichloromethane (DCM) (100 ml) was added to the reaction mixture, and the resulting solid was filtered; 2M Na2CO3 (50 ml) was added to the solution, and the aqueous layer was washed with DCM (3*100 ml). The aqueous layer was acidified with 12N HCl (36 ml) and the title compound was recovered as racemic mixture by filtration (5.1 g, 97% yield). |
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