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Chemical Structure| 4273-92-1 Chemical Structure| 4273-92-1

Structure of 4273-92-1

Chemical Structure| 4273-92-1

N-(4-Chloro-2,5-dimethoxyphenyl)-3-hydroxy-2-naphthamide

CAS No.: 4273-92-1

4.5 *For Research Use Only !

Cat. No.: A124695 Purity: 95%

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Product Details of [ 4273-92-1 ]

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

Safety of [ 4273-92-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H317
Precautionary Statements:P261-P280

Computational Chemistry of [ 4273-92-1 ] Show Less

Physicochemical Properties

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
Ertl P. et al. 2000 J. Med. Chem.

67.79 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.67
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

4.77
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

4.28
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.77
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.88
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.67

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-5.21
Solubility 0.00222 mg/ml ; 0.00000621 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-5.92
Solubility 0.000426 mg/ml ; 0.00000119 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-6.84
Solubility 0.0000515 mg/ml ; 0.000000144 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

Yes
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.1 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.38

Application In Synthesis of [ 4273-92-1 ]

* 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.

  • Downstream synthetic route of [ 4273-92-1 ]

[ 4273-92-1 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 92-70-6 ]
  • [ 6358-64-1 ]
  • [ 4273-92-1 ]
YieldReaction ConditionsOperation 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%.
  • 2
  • [ 4273-92-1 ]
  • Phosphoric acid mono-[3-(4-chloro-2,5-dimethoxy-phenylcarbamoyl)-naphthalen-2-yl] ester [ No CAS ]
  • 3
  • [ 2700-22-3 ]
  • [ 4273-92-1 ]
  • 3-amino-2-cyano-1-phenyl-1<i>H</i>-benzo[<i>f</i>]chromene-5-carboxylic acid (4-chloro-2,5-dimethoxy-phenyl)-amide [ No CAS ]
  • 4
  • [ 4273-92-1 ]
  • [ 2025-40-3 ]
  • 3-amino-5-(4-chloro-2,5-dimethoxy-phenylcarbamoyl)-1-phenyl-1<i>H</i>-benzo[<i>f</i>]chromene-2-carboxylic acid ethyl ester [ No CAS ]
  • 5
  • [ 50-00-0 ]
  • [ 4273-92-1 ]
  • [ 109-77-3 ]
  • 3-amino-2-cyano-1<i>H</i>-benzo[<i>f</i>]chromene-5-carboxylic acid (4-chloro-2,5-dimethoxy-phenyl)-amide [ No CAS ]
  • 6
  • [ 4273-92-1 ]
  • [ 79441-97-7 ]
  • 4-(4,5-diphenyl-1<i>H</i>-pyrazolo[3,4-<i>c</i>]pyridazin-3-ylazo)-3-hydroxy-naphthalene-2-carboxylic acid (4-chloro-2,5-dimethoxy-phenyl)-amide [ No CAS ]
  • 7
  • [ 55805-64-6 ]
  • [ 4273-92-1 ]
  • C.I. Pigment Red 146 [ No CAS ]
YieldReaction ConditionsOperation 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...
  • 8
  • [ 4273-92-1 ]
  • [ 50516-77-3 ]
  • C.I. Pigment Red 146 [ No CAS ]
YieldReaction ConditionsOperation 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:
 

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