Category: 596-38-3

Wan, Peter published the artcileAdiabatic photodehydroxylation of 9-phenylxanthen-9-ol. Observation of carbocation fluorescence in neutral aqueous solution, Safety of 9-Phenyl-9H-xanthen-9-ol, the publication is Journal of Organic Chemistry (1985), 50(16), 2881-6, database is CAplus.

The photobehavior of the title compound (I) is examined in aqueous solution and organic solvents. Aqueous I undergoes adiabatic photodehydroxylation (the first example of a new class of adiabatic photochem. reactions). The reaction is not observed in MeCN and 95% aqueous EtOH. The photogenerated carbocation is trapped by MeOH in aqueous MeOH. The photobehavior of I is due to the enhanced basicity (as measured by the ionization constant pK_R⁺ of the mol. in S₁ relative to that of the ground state (S₀). The enhanced electron-donating effect of the ortho atom of I in the excited singlet state is responsible for this effect.

Journal of Organic Chemistry published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C15H14Cl2S2, Safety of 9-Phenyl-9H-xanthen-9-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Millar, Shannon published the artcileSome observations on detritylation in solid-phase oligonucleotide synthesis, COA of Formula: C19H14O2, the publication is Nucleic Acids Symposium Series (2008), 52(1), 311-312, database is CAplus and MEDLINE.

A symposium. The quality of oligodeoxyribonucleotides prepared by solid phase synthesis under different acid treatment time was compared. Much shorter acid delivery time did not lead to significant decrease of the full length products.

Nucleic Acids Symposium Series published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, COA of Formula: C19H14O2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ou, Wei published the artcileRoom-Temperature Palladium-Catalyzed Deuterogenolysis of Carbon Oxygen Bonds towards Deuterated Pharmaceuticals, Category: alcohols-buliding-blocks, the publication is Angewandte Chemie, International Edition (2021), 60(12), 6357-6361, database is CAplus and MEDLINE.

Site-specific incorporation of deuterium into drug mols. to study and improve their biol. properties is crucial for drug discovery and development. Herein, we describe a palladium-catalyzed room-temperature deuterogenolysis of carbon-oxygen bonds in alcs. and ketones with D₂ balloon for practical synthesis of deuterated pharmaceuticals and chems. with benzyl-site (sp³ C-H) D-incorporation. The highlights of this deoxygenative deuteration strategy are mild conditions, broad scope, practicability and high chemoselectivity. To enable the direct use of D₂O, electrocatalytic D₂O-splitting is adapted to in situ supply D₂ on demand. With this system, the precise incorporation of deuterium in the metabolic position (benzyl-site) of ibuprofen is demonstrated in a sustainable and practical way with D₂O.

Angewandte Chemie, International Edition published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Shen, Guang-Bin published the artcilePrediction of Kinetic Isotope Effects for Various Hydride Transfer Reactions Using a New Kinetic Model, Category: alcohols-buliding-blocks, the publication is Journal of Physical Chemistry A (2016), 120(11), 1779-1799, database is CAplus and MEDLINE.

In this work, kinetic isotope effect (KIE_self) values of 68 hydride self-exchange reactions, XH(D) + X⁺ → X⁺ + XH(D), in acetonitrile at 298 K were determined using a new exptl. method. KIE values of 4556 hydride cross transfer reactions, XH(D) + Y⁺ → X⁺ + YH(D), in acetonitrile were estimated from the 68 determined KIE_self values of hydride self-exchange reactions using a new KIE relation formula derived from Zhu’s kinetic equation and the reliability of the estimations was verified using different exptl. methods. A new KIE kinetic model to explain and predict KIE values was developed according to Zhu’s kinetic model using two different Morse free energy curves instead of one Morse free energy curve in the traditional KIE theories to describe the free energy changes of X-H bond and X-D bond dissociation in chem. reactions. The most significant contribution of this paper to KIE theory is to build a new KIE kinetic model, which can be used to not only uniformly explain the various (normal, enormous and inverse) KIE values but also safely predict KIE values of various chem. reactions.

Journal of Physical Chemistry A published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C6H10N2, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Liu, Gaoxiaozheng published the artcileConcise synthesis of xanthones by the tandem etherification-Acylation of diaryliodonium salts with salicylates, Computed Properties of 596-38-3, the publication is Chinese Chemical Letters (2018), 29(6), 985-988, database is CAplus.

An efficient synthetic method for multi-substituted xanthones, e.g., I was developed. The reaction of diaryliodonium salts (RC₆H₄)₂I⁺OTf^– (R = H, 3-Me, 4-F, etc.) and salicylates R¹C(O)₂CH₃ (R¹ = 4-Br-2-HOC₆H₃, 3-hydroxythiophen-2-yl, 3-hydroxynaphth-2-yl, etc.) was employed for the preparation of the xanthones. This method proceeded through an intermol. etherification-acylation to give target heterocycles in good yields (up to 91%). Multi-substituted xanthones I were gained by shifting the substituent of salicylates or diaryliodonium salts.

Chinese Chemical Letters published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Computed Properties of 596-38-3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Pilkington-Miksa, Michael A. published the artcileTargeting lipopolyplexes using bifunctional peptides incorporating hydrophobic spacer amino acids: Synthesis, transfection, and biophysical studies, Related Products of alcohols-buliding-blocks, the publication is Bioconjugate Chemistry (2007), 18(6), 1800-1810, database is CAplus and MEDLINE.

We have developed efficient synthetic routes to two hydrophobic amino acids, suitably protected for solid-phase peptide synthesis, and have successfully synthesized peptides containing these or other hydrophobic amino acids as spacers between a Lys₁₆ moiety and an integrin-targeting motif. These peptides have in turn been used to formulate a range of lipopolyplex vectors with Lipofectin and plasmid DNA. The transfection efficiencies of these vectors and their aggregation behavior in buffers and in serum have been studied. We have shown that vectors containing peptides incorporating long linkers that are entirely hydrophobic are less efficient transfection agents. However, linkers of equivalent length that are in part hydrophobic show improved transfection properties, which is probably due to the improved accessibility of the integrin-binding motif.

Bioconjugate Chemistry published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Johnston, L. J. published the artcileCharacterization of the triplet excited state of the phenylxanthenium carbocation, Formula: C19H14O2, the publication is Canadian Journal of Chemistry (1992), 70(1), 280-2, database is CAplus.

The triplet excited state of the 9-phenylxanthenium cation is observed directly by both luminescence and transient absorption techniques. The triplet-triplet absorption shows λ_max ≤ 300 nm and decays over a period of several microseconds in the absence of easily oxidized donors. The triplet cation reacts with 9-phenylxanthydrol and biphenyl via electron transfer to give the corresponding radical and radical cation and also reacts rapidly with both oxygen and 1,3-cyclohexadiene.

Canadian Journal of Chemistry published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Formula: C19H14O2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Shriner, R. L. published the artcileThe structure of the nitration products of 9-phenylxanthylium salts, SDS of cas: 596-38-3, the publication is Journal of the American Chemical Society (1951), 891-4, database is CAplus.

cf. preceding abstract The nitration of 9-phenylxanthylium perchlorate (I) yielded 91% 9-(m-nitrophenyl)xanthylium perchlorate (II), as shown by hydrolysis to the carbinol (III) and reduction to 9-(m-nitrophenyl)xanthene (IV). The structure of IV was established by condensation of xanthydrol (V) with ο-O₂NC₆H₄NH₂ (VI) to 9-(4-amino-3-nitrophenyl)xanthene (VII) from which the NH₂ group was removed by diazotization and H₃PO₂. These cationic salts orient the entering NO₂ group to the m-position. Xanthone (VIIIa) and PhMgBr yielded 86% 9-phenylxanthydrol (VIII), m. 158-9° (Gomberg and Cone, C.A. 5, 90). HClO₄ (5.85 g. 70%) added with stirring to 10 g. VIII in 50 cc. C₆H₆ and 25 cc. Me₂CO, and the mixture refrigerated yielded 13.4 g. I, yellow crystals, m. 280-1° (explosive !). Excess FeCl₃-HCl added to 2. g. VIII in HCl yielded 3.14 g. 9-phenylxanthylium ferrichloride, yellow crystals, m. 170°. Cold, concentrated HNO₃ added during 5-10 min. to 10 g. VIII in 50 cc. concentrated H₂SO₄ (ice bath 5-10°), and the mixture poured onto 500 g. ice and neutralized with NH₄OH, yielded 12 g. crude 9-(m-nitrophenyl)xanthydrol (IX), m. 55-9°. HClO₄ (5 cc. 70%) added with stirring to 10 g. IX in 30 cc. 1:1 C₆H₆-Me₂CO, and the mixture allowed to stand (cold) 24 h., yielded 11.3 g. II, yellow crystals from AcOH, m. 255-7° (corrected). Excess FeCl₃-HCl added to 10 g. IX in a min. of concentrated HCl and chilled 24 h. at 5° yielded 13.6 g. 9-(m-nitrophenyl)xanthylium ferrichloride, orange crystals from AcOH, m. 242-3° (corrected). IX (2 g.) in 5 cc. concentrated H₂SO₄ added to 100 cc. MeOH, and the mixture allowed to stand at 20° 30 min. and poured onto 500 g. ice yielded 1.7 g. Me ether, white crystals from MeOH, m. 134-5°; Et ether, white prisms from EtOH, m. 118-19°. Na₂CO₃ (10 g.) added to 50 g. IX in 600 cc. 90% HCO₂H, and the solution refluxed 1-1.5 h. and cooled 4 h. at 5-10° yielded 43.5 g. IV, pale tan crystals from EtOH, m. 155-6°. Cold, concentrated HNO₃ (30 cc.) added during 5-10 min. (stirring) to 10 g. I in 40 cc. concentrated H₂SO₄, and the solution poured into ice water and neutralized with NH₄OH yielded 11.2 g. crude nitrated carbinol, identical with IX. KMnO₄ (50 g.) added with stirring and heating (steam bath) to 3 g. IX in 300 cc. water containing 60 cc. concentrated H₂SO₄, the mixture saturated with SO₂, extracted with Et₂O, and the Et₂O removed, yielded 0.03 g. p-O₂NC₆H₄CO₂H, m. 240° when mixed with an authentic sample. Concentrated H₂SO₄ (140 cc.) added (stirring) to 300 cc. water containing 10 g. IX and 143 g. Na₂Cr₂O₇, 55 cc. H₂SO₄ added dropwise during 30 min., and the mixture refluxed 2 h., cooled, filtered, and washed yielded 0.22 g. p- and 2.6 g. m-O₂NC₆H₄CO₂H. IV (2.0 g.) in 200 cc. absolute alc. reduced with Pt oxide 5-10 min. at 25° and 20 lb. pressure yielded 1.8 g. NH₂ analog (X), white crystals, m. 154-5°. IV (1.0 g.) refluxed 8 h. with 10 cc. concentrated HCl, 15 cc. water, 15 cc. AcOH, and 2 g. Zn yielded 0.2 g. X, m. 153-5°. V (24 g.), 22 g. PhNH₂, 6 cc. concentrated HCl, and 120 cc. AcOH refluxed 4 h., stirred into 2 l. cold water containing 20 g. Na₂CO₃, and the mixture stirred on the steam bath 30 min. and filtered hot yielded 34.5 g. of a mixture of 9-(p-aminophenyl)xanthene (XI) and its Ac derivative (XII). The solid refluxed 6 h. with 70 cc. concentrated HCl and 500 cc. 80% EtOH, cooled, poured into 2 l. cold water, neutralized with Na₂CO₃ and warmed on the steam bath 15-20 min. yielded 20 g. XI, white prisms from EtOH, m. 185°. XI (3 g.) refluxed 6 h. in 25 cc. AcOH and poured into water yielded 2 g. XII, white crystals from EtOH, m. 186-7°. VIIa (6.5 g.) in 30 cc. hot C₆H₆ added to p-MeOC₆H₄MgBr (from 1.2 g. Mg and 9.2 g. p-BrC₆H₄OMe) in 50 cc. Et₂O, and the mixture stirred and refluxed 4 h. and hydrolyzed with NH₄Cl yielded 6 g. 9-(p-methoxyphenyl)xanthydrol (XIII), white prisms from Me₂CO, m. 120-1°. XIII (5 g.) in 100 cc. 90% HCO₂H containing 2 g. Na₂CO₃ refluxed 1 h. yielded 4.3 g. 9-(p-methoxyphenyl)xanthene (XIV), white prisms from EtOH, m. 113-14°. NaNO₂ (2.55 g.) added during 2 h. to 10 g. XI in 30 cc. AcOH and 10 cc. concentrated H₂SO₄, and the mixture poured into 50 cc. H₂SO₄ and 50 cc. water (boiling), boiled 15 min., and poured into ice water yielded 6 g. red solid, m. 130-40°, which, refluxed 20 h. with 0.8 g. NaOH, 3 cc. Me₂SO₄, and 20 cc. water, cooled, and poured into cold water, yielded 2.1 g. XIV, white prisms, m. 113-14° (from MeOH). V (24 g.), 20 g. VI, 10 cc. concentrated HCl, and 120 cc. AcOH refluxed 4 h., cooled to 25°, poured into 1 l. water containing 20 g. Na₂CO₃, and stirred on the steam bath 30 min., yielded 28 g. yellow solid, which, refluxed 8 h. with 400 cc. 80% EtOH and 100 cc. concentrated HCl, cooled, poured into 1 l. cold water, and treated with Na₂CO₃ yielded 17.8 g. VII, yellow crystals from 500 cc. absolute EtOH, m. 160-1°. VI (20 g.) added to 24 g. V in 450 cc. EtOH, 20 cc. AcOH added after solution, and the mixture stirred 2 h. at 25° and cooled 2 h. to 0-5° yielded 36.5 g. 9-(ο-nitrophenylamino)xanthene (XV), orange crystals from pyridine, m. 197-9° (uncorrected). XV (2 g.) refluxed 4 h. in 50 cc. 15% HCl and cooled to room temperature yielded 1.2 g. V, m. 116-20°, and 0.5 g. VI, m. 70-1°. V and AcNH₂ in AcOH (Phillips and Pitt, C.A. 37, 5371.6) yielded N-xanthylacetamide, m. 237-9°. XV (10 g.) refluxed 4 h. in 50 cc. AcOH containing 2 cc. concentrated H₂SO₄, cooled to 25°, poured into 500 cc. water, 5 g. Na₂CO₃ added, and the mixture warmed on the steam bath 30 min. yielded 8.4 g. VII, m. 159-61° (from EtOH). NaNO₂ (2.15 g.) in 10 cc. cold water added dropwise (15 min.) to 10 g. VII in 30 cc. AcOH and 5 cc. concentrated H₂SO₄ at 5°, the mixture stirred 1 h. at 5-10°, 15 cc. cold 50% H₃PO₂ added, the mixture stirred 1 h., kept at 0-5° 16 h., 10 cc. H₃PO₂ added, then 25 cc. water, the solution extracted with three 100-cc. portions of C₆H₆, the combined extracts washed with water, 20% NaOH, and water, and the C₆H₆ removed, yielded 8.1 g. red crystals, m. 120-30°, which, allowed to stand 8 h. at 25° in 125 cc. EtOH, yielded 0.5 g. IV, pale yellow crystals from EtOH, m. 155-6°.

Journal of the American Chemical Society published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C7H8BBrO3, SDS of cas: 596-38-3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Conant, J. B. published the artcileSuperacid solutions. IV. Determination of the strength of weak bases and pseudo bases in glacial acetic acid solution, Recommanded Product: 9-Phenyl-9H-xanthen-9-ol, the publication is Journal of the American Chemical Society (1930), 4436-50, database is CAplus.

cf. C. A. 22, 4035. A spectrophotometric study has been made of the acid-base equilibrium in solutions of crystal violet in buffered glacial AcOH solutions The extinction coefficient was measured at intervals of 10 mμ from 470 to 680. Data are given for the fundamentals chosen for the violet, green and yellow forms; also for the dissociation constants of crystal violet from spectrophotometric data at 25° in urea-H₂SO₄, urea-HClO₄ and acetoxime-H₂SO₄ buffers. The change of pK’₁ for crystal violet with change in ionic strength is shown in the form of curves; this effect is very marked; the total change of pK’₁ from the limiting value at μ = 0 to √μ = 0.5 is about 2.6 p_H units. In the more concentrated solutions there are sp. effects depending on the nature of the neutral salt. These effects are larger than the corresponding effects in H₂O because of the low dielec. constants of AcOH; the natures of both the cation and anion of the neutral salt are important. An electrometric study of weak bases and pseudo bases in glacial AcOH reveals the large effect of changing ionic strength, also noted in the spectrophotometric study. The following apparent pK’ values for pseudo bases at 25° in glacial AcOH are reported (bases in 0.05 M solution titrated with H₂SO₄ μ = 0.2 with Me₃NHSO₃C₆H₄Ne-p): Ph₃COH -1.47; C₁₀H₇CPh₂OH -1.25; (MeOC₆H₄)₂CHOH -1.14; MeOC₆H₄CPh₂OH -0.59; phenylxanthanol 1.91; dinaphthoxanthanol. 2.40 MeOC₆H₄)₃COH, 2.56. The effect of added H₂O on the apparent constants of a number of weak pseudo bases is reported. A method is outlined for obtaining significant values for the relative basicity of the “halochromic carbinols.”

Journal of the American Chemical Society published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Recommanded Product: 9-Phenyl-9H-xanthen-9-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Berger, R. M. published the artcileStable cation formation and luminescence on inorganic oxide surfaces: 9-phenylxanthenyl cation, Application of 9-Phenyl-9H-xanthen-9-ol, the publication is Chemical Physics Letters (1990), 169(3), 213-17, database is CAplus.

The alc. 9-phenylxanthen-9-ol (I) was adsorbed on silica gel and alumina surfaces. Under room temperature conditions the 9-phenylxanthenyl cation (II) was formed and stabilized on silica gel. Steady state fluorescence studies show II fluoresces with λ_max = 210 nm and that this luminescence occurs via both direct excitation of II as well as adiabatic dehydroxylation of the excited singlet of I. Time-resolved experiments show II has a fluorescence lifetime on silica gel of 37 ± 2 ns and is quenched by oxygen at a rate of 1.5 × 10⁴ torr^-1 s^-1.

Chemical Physics Letters published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Application of 9-Phenyl-9H-xanthen-9-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts