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Structure of 13722-96-8

Chemical Structure| 13722-96-8

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Product Details of [ 13722-96-8 ]

CAS No. :13722-96-8
Formula : C7H5NO6
M.W : 199.12
SMILES Code : O=C(O)C1=CC([N+]([O-])=O)=C(O)C=C1O
MDL No. :MFCD08693128
InChI Key :DVHFWKCHUQZGSF-UHFFFAOYSA-N
Pubchem ID :16637915

Safety of [ 13722-96-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 13722-96-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 6.0
Num. H-bond donors 3.0
Molar Refractivity 46.27
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

123.58 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.45
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

2.08
Log Po/w (WLOGP)?

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

0.7
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.

-0.57
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

-1.82
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.17

Water Solubility

Log S (ESOL):?

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

-2.57
Solubility 0.536 mg/ml ; 0.00269 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-4.3
Solubility 0.00987 mg/ml ; 0.0000496 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

-0.01
Solubility 196.0 mg/ml ; 0.984 mol/l
Class?

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

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

No
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

No
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

No
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

No
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

No
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

No
Log Kp (skin permeation)?

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

-6.04 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

1.0
Bioavailability Score?

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

0.56

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

2.0 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<1.0
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)

1.91

Application In Synthesis of [ 13722-96-8 ]

* 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 [ 13722-96-8 ]

[ 13722-96-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 13722-96-8 ]
  • [ 69938-56-3 ]
YieldReaction ConditionsOperation in experiment
63% In a 250 mL four-necked flask equipped with a thermometer and a spherical condenser, 4 g of 5-nitro-2,4-dihydroxybenzoic acid, 0.28 g of Pd / C catalyst, and 60 mL of ethanol were added in a dropwise manner using a constant pressure dropping funnel. 7mL of hydrazine hydrate, heated to reflux temperature, reacted for 4h, stopped heating, filtered the reaction solution while it was hot, and filtered the filtrate into an ice-water bath to cool down for 30min. Add 0.1g of stannous chloride, then add 100mL of concentrated hydrochloric acid, and let stand for 6h , Filtered, and the filter cake was dried to obtain an off-white product. The mass fraction by HPLC analysis was 94.83%, and the yield based on 5-nitro-2,4-dihydroxybenzoic acid was 66.12%.
61.22% With sodium dithionite; water; sodium hydroxide; at 10 - 30℃; for 2h;Large scale; 1000 g of 5-nitro 2,4-dihydroxybenzoic acid was dissolved in 10 L of 5%In aqueous sodium hydroxide solution, add to a 20L four-necked flask and stir to cool to 10-15 C.Start adding 3500 g of sodium dithionite in batches at a temperature of 20-30 C.The system gradually precipitated a yellow solid.When sodium dithionite is added to one third, the system precipitates yellow-green solids which are relatively viscous and difficult to stir.Continue to add about one-third of sodium dithionite, the system is no longer sticky,After the addition was completed, the reaction was stirred at 20-30 C for 2 h (central control 1).The above steps are the key to successful nitro reduction. The inventor of the present application found thatThe effect of adding sodium dithionite to the reaction system in one time is not ideal, and it needs to be added in batches.The amount of each addition should not exceed half of the total amount.It is best not to exceed one third of the total amount (added more than three times), and,The temperature is preferably controlled at 20-30 C.Such a reaction system does not cause a low yield due to viscous or the like.After the reaction is completed, it is filtered, blasted at 60 C for 5 h, and 20 L at 20-30 C for 2 h.After filtration, it was air-dried at 60 C (central control 2).The crude product was beaten with 8 L of water at 20-30 C, filtered and blast dried at 60 C.Obtained 520g of gray solid, (central control 3)The HPLC purity was 98.78%, and the yield was 61.22%.
 

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Technical Information

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