Structure of Sodium 4-aminobenzoate
CAS No.: 555-06-6
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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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Photosensitized activation of diazonium derivatives for C-B bond formation
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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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 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
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 |
66.15 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
-10.06 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.83 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.36 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.12 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.5 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-1.84 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.69 |
Solubility | 3.27 mg/ml ; 0.0206 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.8 |
Solubility | 2.51 mg/ml ; 0.0158 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.38 |
Solubility | 6.6 mg/ml ; 0.0415 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 |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
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 |
-6.68 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 |
1.0 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) |
1.0 |
* 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 |
---|---|---|
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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