Structure of 503821-94-1
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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. : | 503821-94-1 |
Formula : | C7H4BrIO2 |
M.W : | 326.91 |
SMILES Code : | O=C(O)C1=CC=CC(Br)=C1I |
MDL No. : | MFCD15527220 |
Boiling Point : | No data available |
InChI Key : | RBFCXOXAEIWXRW-UHFFFAOYSA-N |
Pubchem ID : | 11232662 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 53.82 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.58 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.79 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.75 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.24 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.86 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.64 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.96 |
Solubility | 0.0357 mg/ml ; 0.000109 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.23 |
Solubility | 0.193 mg/ml ; 0.000589 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.55 |
Solubility | 0.0926 mg/ml ; 0.000283 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 |
-6.31 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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.9 |
* 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 |
---|---|---|
By the same procedure, using <strong>[503821-94-1]3-bromo-2-iodobenzoic acid</strong> as the starting material, 7-bromo-8-iodo-1,2,3,4-tetrahydroisoquinoline is prepared. | ||
By the same procedure, using <strong>[503821-94-1]3-bromo-2-iodo-benzoic acid</strong> as the starting material, 7-bromo-8-iodo-1,2,3,4-tetrahydroisoquinoline is prepared. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; | a) 3-Bromo-2-(2-bromophenylamino)benzoic acid (XXII) 3-Bromo-2-iodobenzoic acid (XX) was prepared as described in D. Twiss and R. V. Heinzelmann, J. Org. Chem. 15 (1950) 496. A mixture of 16.0 g (46 mmol) of sodium 3-bromo-2-iodobenzoate [prepared from 15.0 g (46 mmol) of <strong>[503821-94-1]3-bromo-2-iodobenzoic acid</strong> (XX) and 1.1 g (46 mmol) of sodium hydride], 19.5 g (100 mmol) of sodium 2-bromoanilide [prepared from 17.3 g (100 mmol) of 2-bromoaniline (XXI) and 2.4 g (100 mmol) of sodium hydride] and a spatula-tipfull of copper powder in 100 ml of tetrahydrofuran was heated to reflux for 9 h. The solvent was distilled off, the residue extracted with 0.5 M aqueous sodium hydroxide, and the resulting suspension subjected to centrifugation. The centrifugate was acidified with diluted hydrochloric acid, the precipitated solid was filtered off and dried under high vacuum. Fractional sublimation under high vacuum yielded 6.3 g (37% of theory) of 3-bromo-2-(2-bromophenylamino)benzoic acid (XXII) as a yellow powder with a melting point of 181-182 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In water; at 100℃; | <strong>[503821-94-1]3-bromo-2-iodo benzoic acid</strong> (11) (2.56 g, 7.83 mmol) was dissolved in a KOH solution (KOH 536 mg, 9.6 mmol; H2O 5 mL). The mixture was condensed under vacuum at 100C and the resultant solid was heated under vacuum at 100C for 12 h to yield a dried potassium salt. Metallic sodium (200 mg, 8.35 mmol) was dissolved in 100 mL of MeOH, and 2,3-dimethylphenol (1.09 g, 8.35 mmol) was added. The mixture was condensed and heated under vacuum at 100C for 12 h to yield a dried sodium salt. The sodium salt was dissolved in 15 mL of anhydrous dimethyl sulphoxide, and then tris (2-(2- methoxyethoxy) ethyl)amine (TDA-1, 1.0 mL) was added. The mixture was stirred to reach homogeneity at room temperature under anhydrous conditions, and then CuCl (350 mg) and potassium salt powders of the compound 11 were added. The resultant mixture was stirred at 85C for 4 h, cooled down to room temperature, washed with a NaOH solution (NaOH 200 mg, water 100 mL), filtered with diatomite, and acidified with 1 N HCl to pH value at 2-3. A semisolid precipitate was collected, washed with water, and dried to yield a crude product of 3-bromo-2-(2,3-dimethylphenol)-benzoic acid (12) (2.36g, 7.35 mmol, 75%). The crude product can be used for next reaction directly without purification. | |
With potassium hydroxide; In water; at 100℃; for 12.0h; | Preparation of 3-bromo-2-(2,3-dimethylphenol)benzoic acid (12)<strong>[503821-94-1]3-bromo-2-iodo benzoic acid</strong> (11) (2.56 g, 7.83 mmol) was dissolved in a KOH solution (KOH 536 mg, 9.6 mmol; H2O 5 mL). The mixture was condensed under vacuum at 100 C. and the resultant solid was heated under vacuum at 100 C. for 12 h to yield a dried potassium salt. Metallic sodium (200 mg, 8.35 mmol) was dissolved in 100 mL of MeOH, and 2,3-dimethylphenol (1.09 g, 8.35 mmol) was added. The mixture was condensed and heated under vacuum at 100 C. for 12 h to yield a dried sodium salt. The sodium salt was dissolved in 15 mL of anhydrous dimethyl sulphoxide, and then tris(2-(2-methoxyethoxy)ethyl)amine (TDA-1, 1.0 mL) was added. The mixture was stirred to reach homogeneity at room temperature under anhydrous conditions, and then CuCl (350 mg) and potassium salt powders of the compound 11 were added. The resultant mixture was stirred at 85 C. for 4 h, cooled down to room temperature, washed with a NaOH solution (NaOH 200 mg, water 100 mL), filtered with diatomite, and acidified with 1 N HCl to pH value at 2-3. A semisolid precipitate was collected, washed with water, and dried to yield a crude product of 3-bromo-2-(2,3-dimethylphenol)-benzoic acid (12) (2.36 g, 7.35 mmol, 75%). The crude product can be used for next reaction directly without purification. |