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Chemical Structure| 555-06-6 Chemical Structure| 555-06-6

Structure of Sodium 4-aminobenzoate
CAS No.: 555-06-6

Chemical Structure| 555-06-6

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Product Citations

Product Citations

Ripak, Alexia ; De Kreijger, Simon ; Sampaio, Renato N. ; Vincent, Cooper A. ; Cauet, Emilie ; Jabin, Ivan , et al.

Abstract: Aryl diazonium salts are ubiquitous building blocks in chem., as they are useful radical precursors in organic synthesis as well as for the functionalization of solid materials. They can be reduced electrochem. or through a photo-induced electron transfer reaction. Here, we provide a detailed picture of the ground- and excited-state reactivity of a series of nine rare and earth-abundant photosensitizers with 13 aryl diazonium salts, which also included three macrocyclic calix[4]arene tetradiazonium salts. Nanosecond transient absorption spectroscopy confirmed the occurrence of excited-state electron transfer and was used to quantify cage-escape yields (i.e., the efficiency with which the formed radicals sep. and escape the solvent cage). Cage-escape yields were large; they increased when the driving force for photo-induced electron transfer increased and also tracked with the C-N+2 bond cleavage propensity, among others. A photo-induced borylation reaction was then investigated with all the photosensitizers and proceeded with yields between 9% and 74%.

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Product Details of [ 555-06-6 ]

CAS No. :555-06-6
Formula : C7H6NNaO2
M.W : 159.12
SMILES Code : O=C([O-])C1=CC=C(N)C=C1.[Na+]
MDL No. :MFCD00064395
InChI Key :XETSAYZRDCRPJY-UHFFFAOYSA-M
Pubchem ID :517441

Safety of [ 555-06-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 555-06-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 35.86
TPSA ?

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

66.15 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

-10.06
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

0.83
Log Po/w (WLOGP)?

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

-0.36
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.

-0.12
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

0.5
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-1.84

Water Solubility

Log S (ESOL):?

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

-1.69
Solubility 3.27 mg/ml ; 0.0206 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-1.8
Solubility 2.51 mg/ml ; 0.0158 mol/l
Class?

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

Very 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

-1.38
Solubility 6.6 mg/ml ; 0.0415 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

Yes
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.

-6.68 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.

0.55

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

1.0 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)

1.0

Application In Synthesis of [ 555-06-6 ]

* 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 [ 555-06-6 ]

[ 555-06-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 3847-57-2 ]
  • [ 555-06-6 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; In water; at 39.84℃; General procedure: Kinetic experiments were performed at 313 K, according to the following procedure. In a quartz cuvette the proper amount of a stock solution of catalyst (1.0 mM) was diluted in the proper amount of freshly double-distilled water (degassed with a fine stream of Ar for 15 min), in such a way to have 2.65mL of solution; then, 100L of a stock solution 3.0 mM of the substrate were added, and the mixture was thermostated. A 48.0 mM solutionof NaBH4 was prepared just before use by dissolving a weighed amount in a volumetric flask; then 250 L were rapidly introduced in the cuvette, and the registration of the kinetic trace immediately started, following by UV-vis spectrophotometry the disappearance of the nitroarene substrate.
With sulfuric acid; tin(IV) oxide; at 85℃; for 2h; General procedure: In a 10 ml three-necked flask equipped with an electric stirrer, a thermometer, a condenser and a dropping funnel, 5 mL of deionized water and 3 g of chromic anhydride were mixed and homogenized. The flask was then immersed in an ice-water bath and cooled to 25 C, The pH was adjusted to 6.0 with a hydrochloric acid solution having a mass fraction of 30%. Then, 3 g of p-nitrotoluene and 10 mL of glacial acetic acid were added thereto, and the liquid was heated to the condenser by a beaker to keep the temperature for 30 minutes. After the above- Add 80 mL of deionized water to the beaker using a dropping funnel and adjust the dropping rate to drop it in 5 min and allow to stand until no yellowish precipitate is produced. Then, the filtrate is filtered under reduced pressure. The resulting extract was placed in a round bottom beaker and 40 mL of a 40% sodium hydroxide solution with a mass fraction of 40% was added and stirred until the filter was completely dissolved, and then the resulting filtrate was air- And then 70kg of titanium dioxide, mixed evenly, in the beaker with a round bottom beaker and add the rotor, then round bottom beaker moved to the magnetic stirring heater, the temperature is set to 70 C, the speed is set to 200r / min; After the solution in the beaker has been clarified, the heating is stopped and the mixture is naturally cooled to room temperature. The liquid in the beaker is poured into a conical flask to remove the titanium dioxide. The aqueous solution is then adjusted to a pH of 7.5 with a mass fraction of 20% The conical flask is then heated until it has a pale yellow precipitateThe resulting filter material was placed in a beaker, and 1.5 g of tin dioxide was added thereto, and the resulting filtrate was added to a beaker, and the mixture was filtered and the filtrate was collected under reduced pressure. Uniform, and then use the mass fraction of 30% sulfuric acid solution soak the mixture, and then the beaker heating, heated to a temperature of 85 C, keep the temperature 2h, the hot filter, collecting the filtrate, 4-aminobenzoate; The resulting filtrate was mixed with 10 g of sodium carbonate and 30 mL of absolute ethanol, poured into a round bottom flask, and then 15 mL of hydrogen bromide was poured into it, and the vessel was transferred to a water bath. After the temperature was set to 60 C and the temperature was maintained for 70 min, the round bottom flask was charged with a distillation unit, and the round bottom flask was heated to collect 135 C fraction and cooled to room temperature to give (2 - ((4-aminobenzene Formyl) oxy) ethyl) in a yield of 47.8%.
 

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