Structure of 4273-92-1
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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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CAS No. : | 4273-92-1 |
Formula : | C19H16ClNO4 |
M.W : | 357.79 |
SMILES Code : | O=C(NC1=CC(OC)=C(Cl)C=C1OC)C2=C(O)C=C3C=CC=CC3=C2 |
MDL No. : | MFCD00043903 |
Boiling Point : | No data available |
InChI Key : | QIHKTBRNOLQDGQ-UHFFFAOYSA-N |
Pubchem ID : | 77955 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H317 |
Precautionary Statements: | P261-P280 |
Num. heavy atoms | 25 |
Num. arom. heavy atoms | 16 |
Fraction Csp3 | 0.11 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 98.18 |
TPSA ? Topological Polar Surface Area: Calculated from |
67.79 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.67 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.77 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.28 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.77 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.88 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.67 |
Log S (ESOL):? ESOL: Topological method implemented from |
-5.21 |
Solubility | 0.00222 mg/ml ; 0.00000621 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.92 |
Solubility | 0.000426 mg/ml ; 0.00000119 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-6.84 |
Solubility | 0.0000515 mg/ml ; 0.000000144 mol/l |
Class? Solubility class: Log S scale |
Poorly 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) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.1 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 |
0.55 |
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) |
2.38 |
* 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% | In water; chlorobenzene; toluene; at 85℃; for 5h; | 1. 1 part of the material 2-hydroxy-3-naphthoic acid (the amount of the substance,The same below) dissolved in water and immiscible solvent 1.1 (such as toluene, chlorobenzene),The solution was added to the reactor (Figure 1),Then, 1.15 parts of 2,5-dimethoxy-4-chloroaniline was added,The reaction mixture was heated at a temperature of 85 C,The reaction time was 5h, and the crude product was obtained in 89% yield.2. Distillation of crude products, the yield of 94%.3. Add the refined product to a separate dryer (Figure 2)The rising steam is evenly contacted with the crude phenol concentrate through the steam distributor,Water vapor cold liquid liquefaction into small water droplets, dissolved products in the soluble impurities,Excessive steam is condensed at the top of the condenser to form a stream of water into the desiccator to rinse the phenolic AS-LC product,After repeated rinsing three times, finally, in the jacket outside the dryer through the water vapor,The dryer was dried by heating to give the final product in a yield of 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; sodium acetate; In water; at 5 - 20℃; for 0.116667 - 1h;pH 4.0;Industry scale;Product distribution / selectivity; | 3-Amino-4-methoxybenzanilide was diazotized in a manner known per se in the art by using a 3.5-fold molar amount of hydrochloric acid and an equimolar amount of sodium nitrite, followed by the addition of sodium acetate to prepare a 0.025 mole/L diazo solution of pH 4.0 (40 L, solution temperature: 5 C.). On the side, N-(4-chloro-2,5-dimethoxyphenyl)-3-hydroxy-2-napthaleneca rboxamide (<strong>[4273-92-1]naphthol AS-LC</strong>) (362 parts) was dissolved in an aqueous solution, which contained sodium hydroxide (100 parts), to prepare a 0.126 mole/L grounding solution (8 L, solution temperature: 20 C.) As illustrated in FIG. 1, the diazo solution was next caused to flow as a first fluid I at a flow rate of 6 L/min by the feed pump d from the first feed tank 2 into the ejector 1 through the first flow path a. Owing to depressurization occurred in the ejector 1, the grounding solution was drawn as a second fluid II at a flow rate of 1.2 L/min (adjusted by the first flow control means e) from the second feed tank 3 through the second flow path b into the ejector 1 maintained at 20 C. by the temperature control means g, and through a coupling reaction, a naphthol AS pigment [C.I. Pigment Red 146 (PR146)] was yielded. The yield of the naphthol AS pigment was very good owing to the effects of a severe turbulence occurred concurrently with the coupling reaction in the ejector. The degree of an excess of the grounder component relative to the diazo component was as much as about 1 mole %. Nonetheless, the coupling reaction proceeded smoothly, and the coupling reaction time was about 7 min. The thus-obtained aqueous suspension of the resulting pigment was discharged from the ejector 1 through the third flow path a', and was stored in the treatment tank 5. After the thus-stored aqueous suspension of the pigment was heated to 90 C., the pigment was collected by filtration, washed with water and then dried to obtain the naphthol AS pigment (PR146) in a dry form.; A diazo solution was prepared in a similar manner as in Example 3. On the side, N-(4-chloro-2,5-dimethoxyphenyl)-3-hydroxy-2-napthaleneca rboxamide (<strong>[4273-92-1]naphthol AS-LC</strong>) (376 parts) was dissolved in an aqueous solution, which contained sodium hydroxide (100 parts), to prepare a 0.131 mole/L grounding solution (8 L, solution temperature: 20 C.). The diazo solution was charged in a batchwise single reaction tank equipped with a stirrer, and under stirring, the grounding solution was charged over 1 hour to form a naphthol AS pigment (PR146). The degree of an excess of the grounder component relative to the diazo component was 5 mole %. After the resulting aqueous suspension of the pigment was heated to 90 C., the pigment was collected by filtration, washed with water and then dried to obtain the naphthol AS pigment (PR146) in a dry form.; 3-Amino-4-methoxybenzanilide was diazotized in a manner known per se in the art by using a 3.5-fold molar amount of hydrochloric acid and an equimolar amount of sodium nitrite, followed by the addition of sodium acetate to prepare a 0.05 mole/L diazo solution of pH 4.0 (20 L, solution temperature: 5 C.). As a grounding solution, on the other hand, the grounding solution (8L, solution temperature: 20 C.) prepared in Example 3 was used. As illustrated in FIG. 3, the diazo solution was next caused to flow as a first fluid I at a flow rate of 5 L/min by the feed pump d from the first feed tank 2 into the ejector 1 through the first flow path a. Owing to depressurization occurred in the ejector 1, the grounding solution was drawn as a second fluid II at a flow rate of 1 L/min (adjusted by the first flow control means e) from the second feed tank 3 through the second flow path b into the ejector 1 maintained at 20 C. by the temperature control means g, and through a coupling reaction, a naphthol AS pigment (PR146) was yielded. A mixture of the resulting suspension of the naphthol AS pigment (PR146) and the diazo solution was recirculated to the first feed tank 2 through the fourth flow path a, and was again fed by the feed pump d to the ejector 1 through the first flow path a. The recirculation was continued until the grounding solution to be drawn through the second flow path b became no longer remaining. The drawn rate of the grounding solution was gradually reduced by the first flow control means e. The yield of the naphthol AS pigment was very good owing to the effects of a severe turbulence occurred concurrently with the coupling reaction in the ejector. The degree of an excess of the grounder component relative to the diazo component was as much as about 1 mole %. Nonetheless, the coupling reaction proceeded smoothly, and the coupling reaction time was about 30 min. The aqueous suspension of the resulting pigment was discharged from the ejector 1 through the third flow path a', and was stored in the treatment tank 5. After the thus-stored aqueous suspension of the pigment was heated to 90 C., the pigment was collected by filtration, washed with water, and then d... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1) Ordinary reactor plus 150ml water,20g content of 30% hydrochloric acid,Add 12g 3-amino-4-methoxybenzoylaniline stirring 30min;Then, slowly add 30% sodium nitrite solution 11.5g at 0C to diazotize and stir for 1 hour.Excess sodium nitrite was removed with sulfamic acid to obtain diazo solution;Industrial use of sodium acetate 40g, emulsifier MOA-4 0.2g directly into the diazo solution and stirred for 10 minutes,That is, diazo solution preparation is completed;Then put it into the coupling reactor,Adjust the amount of water 100ml to be coupled reaction.2)Ordinary reactor water 150g, 30% liquid caustic 17.1g, detergent 209, 0.92g, stirring is turned on, heated to 85-90 C, add <strong>[4273-92-1]naphthol AS-LC</strong> 18.6g to stir dissolved clear;Then quickly add ice to cool down to 20-25C.Adjust the amount of fluid to be reacted.3)The coupling component solution is added to the coupling reaction vessel at 0-15 C. for anti-coupling reaction.Maintain reaction time 50-60min,Control the end point of pH = 5.5-6, diazo solution added after stirring for 1.5 hours;4)The post-treatment stage heats up to 90-95C,Insulation for 30 minutesCooling filtration,The pigment red 30g is dried at 85C.The application properties of the pigment red:Lightfastness level 5,Heat-resistant 220C; Transparency ?L*=1.20 (Judgement -0.5T),Gloss: |