Structure of 556-97-8
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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. : | 556-97-8 |
Formula : | C8H9Cl |
M.W : | 140.61 |
SMILES Code : | CC1=CC(C)=CC(Cl)=C1 |
MDL No. : | MFCD00060273 |
Boiling Point : | No data available |
InChI Key : | FKKLHLZFSZGXBN-UHFFFAOYSA-N |
Pubchem ID : | 32887 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 41.38 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.4 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.88 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.96 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.53 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.41 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.24 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.65 |
Solubility | 0.0315 mg/ml ; 0.000224 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.58 |
Solubility | 0.0372 mg/ml ; 0.000265 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.76 |
Solubility | 0.0244 mg/ml ; 0.000174 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
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) |
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 |
-4.4 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 |
2.0 |
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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.0 |
* 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 |
---|---|---|
In potassium permanganate; water; | f) Preparation of 5-chloroisophthalic acid In a 5 liter 3-necked round-bottomed flask equipped with mechanical stirrer, condenser, nitrogen inlet and thermometer were placed 5-chloro-m-xylene (112 g, 0.8 mole), water (840 ml) and 2-methyl-2-propanol (1200 ml). The resulting solution was warmed up to 70 C. and solid potassium permanganate (50 g) was added. The reaction was refluxed until the purple color was gone; the reaction mixture was then cooled down to 70 C. and another portion (50 g) of potassium permanganate was added and the reaction mixture refluxed until the purple color was gone. In this way a total of 700 g of potassium permanganate was added. After the color of the last addition of potassium permanganate was gone, the reaction mixture was cooled down to approximately 35-40 C. and filtered through celite. The manganese dioxide cake was washed several times with 2% aqueous sodium hydroxide, the combined filtrates were made acidic with concentrated hydrochloric acid and extracted with ethyl acetate (5*500 ml). The combined organic layers were washed with water (3*500 ml), dried over magnesium sulfate and concentrated in a rotavap yielding 5-chlorophthalic acid as a white solid (134.5 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; N-Bromosuccinimide; potassium tert-butylate; silver nitrate; dibenzoyl peroxide; In tetrachloromethane; water; | 3-Chloro-5-methylbenzoic acid A well stirred mixture of N-bromosuccinimide (32.5 g), 5-chloro-m-xylene (25.6 g) and carbon tetrachloride (500 ml) is refluxed for 8 hours. The solution is well illuminated and every 2 hours small quantities of benzoyl peroxide are added. The cooled mixture is filtered and the solvent evaporated to give an oil consisting of a mixture of 3-chloro-5-methylbenzyl bromide and 5-chloro-m-xylene in a ratio of about 2:1 (34.5 g). The above mixture is added to a stirred mixture of potassium tert-butoxide (14 g), 2-nitropropane (11 g) and dimethylsulphoxide (100 ml) and the mixture is stirred overnight at room temperature. Water (500 ml) is added and the separated oil extracted with ether. Evaporation of the dried ether solution yields an oil consisting of a mixture of <strong>[103426-20-6]3-chloro-5-methyl-benzaldehyde</strong> and 5-chloro-m-xylene (approximately 1:1) (18.5 g). The above mixture is slowly added over a 15 minute period to a stirred suspension of moist silver oxide [prepared from silver nitrate (24 g) and an aqueous solution of sodium hydroxide (5.7 g)] in a solution of sodium hydroxide (5.7 g) in water (50 ml). The stirred mixture is refluxed for 30 minutes, cooled, filtered and the filtrate extracted with ether. Acidification of the aqueous layer with 2N HCl yields a precipitate which is filtered and recrystallized from aqueous methanol to yield 3-chloro-5-methylbenzoic acid, 174-175 C. (9.4 g). | |
With hydrogenchloride; sodium hydroxide; N-Bromosuccinimide; potassium tert-butylate; silver nitrate; dibenzoyl peroxide; In tetrachloromethane; water; | 3-Chloro-5-methylbenzoic acid A well stirred mixture of N-bromosuccinimide (32.5 g), 5-chloro-m-xylene (25.6 g) and carbon tetrachloride (500 ml) is reflexed for 8 hours. The solution is well illuminated and every 2 hours small quantities of benzoyl peroxide are added. The cooled mixture is filtered and the solvent evaporated to give an oil consisting of a mixture of 3-chloro-5-methyl-benzyl bromide and 5-chloro-m-xylene in a ratio of about 2:1 (34.5 g). The above mixture is added to a stirred mixture of potassium tert-butoxide (14 g), 2-nitropropane (11 g) and dimethylsulphoxide (100 ml) and the mixture is stirred overnight at room temperature. Water (500 ml) is added and the separated oil extracted with ether. Evaporation of the dried ether solution yields an oil consisting of a mixture of <strong>[103426-20-6]3-chloro-5-methyl-benzaldehyde</strong> and 5-chloro-m-xylene (approximately 1:1) (18.5 g). The above mixture is slowly added over a 15 minute period to a stirred suspension of moist silver oxide [prepared from silver nitrate (24 g) and an aqueous solution of sodium hydroxide (5.7 g)] in a solution of sodium hydroxide (5.7 g) in water (50 ml). The stirred mixture is refluxed for 30 minutes, cooled, filtered and the filtrate extracted with ether. Acidification of the aqueous layer with 2N HCl yields a precipitate which is filtered and recrystallized from aqueous methanol to yield 3-chloro-5-methylbenzoic acid, 174-5 C. (9.4 g). |
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