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Structure of 2,3-Dichlorobenzaldehyde
CAS No.: 6334-18-5
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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'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 6334-18-5 |
Formula : | C7H4Cl2O |
M.W : | 175.01 |
SMILES Code : | O=CC1=CC=CC(Cl)=C1Cl |
MDL No. : | MFCD00010127 |
InChI Key : | LLMLNAVBOAMOEE-UHFFFAOYSA-N |
Pubchem ID : | 35745 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H314-H412 |
Precautionary Statements: | P273-P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310 |
Class: | 8 |
UN#: | 1759 |
Packing Group: | Ⅲ |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 41.85 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.77 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.96 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.81 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.63 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.26 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.69 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.17 |
Solubility | 0.119 mg/ml ; 0.000679 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.98 |
Solubility | 0.183 mg/ml ; 0.00104 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.57 |
Solubility | 0.0467 mg/ml ; 0.000267 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) |
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 |
-5.27 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 |
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) |
1.12 |
* 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 |
---|---|---|
62% | In hexane; isopropyl alcohol; | Step B. Synthesis of Felodipine In a four necked, 3 liter flask, a solution of MBI (about 268.4 g, 0.98 mole) in isopropanol was brought to reflux and a solution of ethyl 3-aminocrotonate (about 114.2 g, 0.8 mole) in isopropanol was added at such a rate to maintain the internal temperature at about 81-83 C. and refluxed for about 1 hour. The temperature of the reaction was then lowered to about 40-50 C. and excess isopropanol removed under reduced pressure maintaining the internal temperature at about 40-45 C. to furnish a viscous yellow orange residue. LC analysis of this residue indicated about 75% felodipine product, 13% MBI, 4% dichlorobenzaldehyde and about 0.5% symmetrical dimethyl dihydropyridine analog and about 0.4% diethyl dihydropyridine analog. Hexane was added to the residue and the suspension stirred under reflux for about 1 hr. The temperature was allowed to fall to about 40 C. during which solids formed. The solids were filtered and washed with fresh hexane and dried to yield felodipine in about 62% yield. LC analysis indicated about 92.8% purity of felodipine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Potassium cyanide (500 mg, 7.7 mmol) and 2-aminoacetamidine dihydrobromide (1.77 g, 7.5 mmol) were stirred in methanol (15 ml) at room temperature for 1 hour. 2,3-Dichlorobenzaldehyde (1.34 g, 7.68 mmol) was added and the suspension was stirred at room temperature overnight. Lithium hydroxide monohydrate (1.0 g, 23.8 mmol) was added and the mixture was stirred whilst open to the atmosphere at room temperature for 24 hours. The reaction mixture was partitioned between ethyl acetate (80 ml) and water (50 ml). The ethyl acetate solution was washed with water (30 ml), then dried over anhydrous sodium sulphate and evaporated in vacuo to give a light brown gum. This was purified using silica gel column chromatography, eluting with ethyl acetate, to furnish 370 mg of the title product as a brown gum. 1HNMR (CDCl3): 4.26 (br s, 2H), 4.43 (br s, 2H), 7.26 (d, 1H), 7.31 (m, 1H), 7.46 (s, 1H), (7.50 (d, 1H) MS m/z 257 [MH]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | To a solution of 2,3-dichlorobenzaldehyde (8.76 g, 0.05 mol) in isopropanol (80 mL) is added picolinic acid (0.65 g, 5.4 mmol), piperidine (0.45 g, 5.4 mmol) and methyl acetoacetate (86.3 g, 0.06 mol). The solution is stirred at 40-45 C. for 6 h, and then isopropanol is distilled under vacuum. The residue is dissolved in ethyl acetate (80 mL) and washed with water (60 mL). Ethyl acetate is then removed under vacuum. To the residue is added ethyl aminocrotonate (7.74 g, 0.06 mol) and isopropanol (60 mL). The mixture is heated under reflux for 4 hours. Isopropanol is distilled and heptanes (60 mL) is added. The resulting solid is filtered and washed with heptanes. After drying 12.7 g (66%) felodipine is obtained as pale yellow solid with a purity of 94.4% (diethyl and dimethyl have a concentration of 2.02% and 3.38% (a/a), respectively). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formic acid; hydroxylamine hydrochloride; sodium acetate; In water; at 80℃; | General procedure: A mixture of aromatic aldehydes (50mmol) (1?17), hydroxylamine hydrochloride (62.5mmol), sodium acetate (125mmol) were dissolved in the mixture of formic acid and water (60:40) and stirred at 80°C until TLC analysis indicated the disappearance of aromatic aldehydes. Then, cooling the reaction system to room temperature and put it into water to obtain the target compounds. Some desired products which were dissolved in the mixture of water and formic acid can be obtained by salting out. Then, solid target compounds were obtained by filtration and recrystallized by alcohol, and then dried under vacuum. While, some target compounds are oily. These oily compounds were obtained by extraction with ethyl acetate and the solvent was removed at the vacuum to afford aryl nitriles (a1?a17). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.3% | 20.0-dichlorobenzaldehyde 70.0 g (0.40 mol), beta-aminocrotonate ethyl ester in a 500 mL round bottom flask55.8g (0.48mol),62.0 g (0.48 mol) of methyl acetoacetate, followed by 4.5 g (0.053 mol) of piperidine and 4.2 g (0.053 mol) of pyridine.The heating was started slowly and the temperature was raised. The reaction was maintained at 75-80 C for 9 h, and 200 g of absolute ethanol was added while heating, and the mixture was heated to reflux for 1 h, and filtered while hot.The mixture was cooled to 15 C and stirred for 1 h, and suction filtered. The filter cake was washed with a small amount of dry ethanol and dried to give 145 g of pale yellow solid.Yield: 94.3%, purity 99.1% |