Structure of 39183-17-0
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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. : | 39183-17-0 |
Formula : | C6H5Cl2NO |
M.W : | 178.02 |
SMILES Code : | OC1=CC=C(N)C(Cl)=C1Cl |
MDL No. : | MFCD14455913 |
InChI Key : | OQHWFUQNSLMSBG-UHFFFAOYSA-N |
Pubchem ID : | 9877529 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 42.89 |
TPSA ? Topological Polar Surface Area: Calculated from |
46.25 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.57 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.7 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.29 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.02 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.94 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.1 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.09 |
Solubility | 0.145 mg/ml ; 0.000815 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.32 |
Solubility | 0.0844 mg/ml ; 0.000474 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.69 |
Solubility | 0.361 mg/ml ; 0.00203 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 |
-5.47 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 |
1.0 |
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 |
2.0 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) |
1.4 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium tetrahydroborate In ethanol at 20℃; for 4 h; Cooling with ice | Equipped with a stirrer and a reflux condenser 100 ml two-necked flask, was added 8.0 g (0.03 mol) of starting material 2,3-dichloro-4-phenylazophenol, 1 g of sodium hydroxide dissolved in 40 ml ethanol, ice-water bath, sodium borohydride was added in small portions 4.5 g (0.12 mol). After completion of the dropwise addition, the ice bath was removed and the mixture was stirred, warmed to room temperature, the reaction was continued for 4 hours. After completion of the reaction, was added diluted hydrochloric acid solution to pH = 7, extracted three times with ethyl acetate, the combined organic phase was dried over anhydrous sodium sulfate, the solvent was distilled off rotary evaporator, was recrystallized from 20 ml of toluene, filtered and dried to give the product pale pink crystals 5.08 g, 95percent yield, 100percent pure. |
139 kg | With sodium dithionite; sodium hydroxide In ethanol; water at 40℃; for 4 h; Large scale | Step 3, the azo obtained in step 2 is put into a reduction kettle. 500 kg of ethanol and 500 kg of water are added, and the temperature is raised to 40 ° C. First, 12.5 kg of sodium hydroxide is added to adjust the pH to 10, and then 50 kg of insurance powder is added ( Sodium dithionite, Na2O4S2). Repeatedly add 12.5kg of sodium hydroxide and 50kg of insurance powder 7 times. After the addition, the reaction is kept at this temperature for 4 hours. The azo is reduced by the action of the powder to form crude 2,3-dichloro-4-hydroxyaniline and aniline. Subsequently, the temperature was raised to 60 ° C and ethanol, water and reduced aniline were recovered under a vacuum of -0.087 MPa, and about 700 kg of the mixture was recovered after 4 hours of recovery. After the recovery, 800 kg of water was added to the crude 2,3-dichloro-4-hydroxyaniline, the temperature was raised to 60 ° C, the temperature was kept for 1 hour, the temperature was lowered to 30 ° C, and the mixture was centrifuged at 3,300 rpm for 10 minutes to obtain 180 to 200 kg of centrifugation. The material is removed by water washing to remove impurities such as water-soluble inorganic salts; the centrifugal material is recrystallized by using 99percent toluene to remove organic impurities, specifically: the centrifuge is put into the reaction vessel, 500 kg of toluene is added, and the temperature is raised to 84 ° C. The temperature was kept at this temperature for 1 hour, the temperature was lowered to 25 ° C, and the mixture was further centrifuged at 3,300 rpm for 10 minutes, and dried at 70 ° C for 3 hours to obtain 2,3-dichloro-4-hydroxyaniline. Among them, the weight of 2,3-dichloro-4-hydroxyaniline is 138-139 kg, the content is 98.0percent, the yield is 96percent, and the specific reduction of azo to 2,3-dichloro-4-hydroxyaniline The process is as shown in equation (3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With hydrogenchloride; sodium hydroxide; hydrogen; aniline; sodium nitrite In methanol; water | EXAMPLE 6 At 0 to 5° C., a solution of 3.8 g (0.055 mol) of NaNO2 in 6 ml of H2 O is added dropwise to 25 ml of aqueous HCl (15percent) and 4.9 g (0.0525 mol) of aniline in a 100 ml two-neck flask fitted with internal thermometer and magnetic stirrer. After 10 minutes, this diazonium salt solution is added at 5 to 10° C. to a solution of 8.15 g (0.05 mol) of 2,3-dichlorophenol and 10 g (0.25 mol) of NaOH in 100 ml of H2 O. The mixture is allowed to warm to room temperature, stirred for a further 1 hour and neutralized with aqueous HCl (pH=7). In a 500 ml three-neck flask fitted with internal thermometer, stirrer and gas inlet tube, this solution is admixed with 300 ml of methanol, 2.5 g of Raney nickel and 15 μl of bis(2-hydroxyethyl) sulphide, and the flask is flushed with argon. At 40 to 50° C., 2300 ml of hydrogen (0.1 mol) are then applied with a pressure of about 1 bar over 1.5 hours. The reaction mixture is admixed with a little activated charcoal, stirred for a further 15 minutes and filtered over a bed of silica gel. The methanol is distilled off and pure 4-hydroxy-2,3-dichloroaniline precipitates from the aqueous solution, giving a yield of 83percent. |
Tags: 39183-17-0 synthesis path| 39183-17-0 SDS| 39183-17-0 COA| 39183-17-0 purity| 39183-17-0 application| 39183-17-0 NMR| 39183-17-0 COA| 39183-17-0 structure
A317739 [61693-43-4]
2,4-Dichloro-3-aminophenol hydrochloride
Similarity: 0.87
A317739 [61693-43-4]
2,4-Dichloro-3-aminophenol hydrochloride
Similarity: 0.87
A317739 [61693-43-4]
2,4-Dichloro-3-aminophenol hydrochloride
Similarity: 0.87
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