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Cas Database

90-46-0

90-46-0

Identification

  • Product Name:Xanthene, hydroxy-

  • CAS Number: 90-46-0

  • EINECS:201-996-1

  • Molecular Weight:198.221

  • Molecular Formula: C13H10O2

  • HS Code:29329990

  • Mol File:90-46-0.mol

Synonyms:Xanthen-9-ol(6CI,7CI,8CI);9H-Xanthen-9-ol;9-Xanthydrol;NSC 4038;Xanthydrol;

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Safety information and MSDS view more

  • Pictogram(s):FlammableF,ToxicT

  • Hazard Codes:F,T,Xi,Xn

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:Xanthydrol
  • Packaging:1g
  • Price:$ 55
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Xanthydrol 98%
  • Packaging:5g
  • Price:$ 48.9
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Xanthydrol for the detection of urea, ≥99.0% (HPLC)
  • Packaging:25g
  • Price:$ 177
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Xanthydrol 98%
  • Packaging:25g
  • Price:$ 158
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Xanthydrol for the detection of urea, ≥99.0% (HPLC)
  • Packaging:100g
  • Price:$ 575
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  • Manufacture/Brand:Chem-Impex
  • Product Description:9-Hydroxyxanthene,99+% 99+%
  • Packaging:1KG
  • Price:$ 2234.4
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  • Manufacture/Brand:Chem-Impex
  • Product Description:9-Hydroxyxanthene 99+%
  • Packaging:250G
  • Price:$ 710
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  • Manufacture/Brand:Chem-Impex
  • Product Description:9-Hydroxyxanthene,99+% 99+%
  • Packaging:100G
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  • Manufacture/Brand:Chem-Impex
  • Product Description:9-Hydroxyxanthene 99+%
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  • Manufacture/Brand:Chem-Impex
  • Product Description:9-Hydroxyxanthene,99+% 99+%
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Relevant articles and documentsAll total 39 Articles be found

A highly reactive P450 model compound I

Bell, Seth R.,Groves, John T.

, p. 9640 - 9641 (2009)

(Graph Presented) The detection and kinetic characterization of a cytochrome P450 model compound I, [OFeIV-4-TMPyP]+ (1), in aqueous solution shows extraordinary reaction rates for C-H hydroxylations. Stopped-flow spectrophotometric monitoring of the oxidation of Fe III-4-TMPyP with mCPBA revealed the intermediate 1, which displays a weak, blue-shifted Soret band at 402 nm and an absorbance at 673 nm, typical of a porphyrin π-radical cation. This intermediate was subsequently transformed into the well-characterized OFeIV-4-TMPyP. Global analysis afforded a second-order rate constant k1 = (1.59 ± 0.06) × 10 7 M-1 s-1 for the formation of 1 followed by a first-order decay with k2 = 8.8 ± 0.1 s-1. 1H and 13C NMR determined 9-xanthydrol to be the major product (~90% yield) of xanthene oxidation by 1. Electrospray ionization mass spectrometry carried out in 47.5% 18OH2 indicated 21% 18O incorporation, consistent with an oxygen-rebound reaction scenario. Xanthene/xanthene-d2 revealed a modest kinetic isotope effect, kH/kD = 2.1. Xanthene hydroxylation by 1 occurred with a very large second-order rate constant k3 = (3.6 ± 0.3) × 106 M-1 s-1. Similar reactions of fluorene-4-carboxylic acid and 4-isopropyl- and 4-ethylbenzoic acid also gave high rates for C-H hydroxylation that correlated well with the scissile C-H bond energy, indicating a homolytic hydrogen abstraction transition state. Mapping the observed rate constants for C-H bond cleavage onto the Bronsted- Evans-Polanyi relationship for similar substrates determined the H-OFe IV-4-TMPyP bond dissociation energy to be ~100 kcal/mol. The high kinetic reactivity observed for 1 is suggested to result from a high porphyrin redox potential and spin-state-crossing phenomena. More generally, subtle charge modulation at the active site may result in high reactivity of a cytochrome P450 compound I.

Meso-Substitution Activates Oxoiron(IV) Porphyrin π-Cation Radical Complex More Than Pyrrole-β-Substitution for Atom Transfer Reaction

Fukui, Nami,Ueno, Kanako,Hada, Masahiko,Fujii, Hiroshi

supporting information, p. 3207 - 3217 (2021/03/01)

There have been two known categories of porphyrins: a meso-substituted porphyrin like meso-tetramesitylporphyrin (TMP) and a pyrrole-β-substituted porphyrin like native porphyrins and 2,7,12,17-tetramethyl-3,8,13,18-tetramesitylporphyrin (TMTMP). To reveal the chemical and biological function of native hemes, we compare the reactivity of the oxoiron(IV) porphyrin π-cation radical complex (Compound I) of TMP (TMP-I) with that of TMTMP (TMTMP-I) for epoxidation, hydrogen abstraction, hydroxylation, sulfoxidation, and demethylation reactions. Kinetic analysis of these reactions indicated that TMP-I is much more reactive than TMTMP-I when the substrate is not sterically bulky. However, as the substrate is sterically bulkier, the difference of the reactivity between TMP-I and TMTMP-I becomes smaller, and the reactivity of TMP-I is comparable to that of TMTMP-I for a sterically hindered substrate. Since the redox potential of TMP-I is almost the same as that of TMTMP-I, we conclude that TMP-I is intrinsically more reactive than TMTMP-I for these atom transfer reactions, but the steric effect of TMP-I is stronger than that of TMTMP-I. This is contrary to the previous result for the single electron transfer reaction: TMTMP-I is faster than TMP-I. DFT calculations indicate that the orbital energies of the Fe=O moiety for TMTMP-I are higher than those for TMP-I. The difference in steric effect between TMP-I and TMTMP-I is explained by the distance from the mesityl group to the oxo ligand of Compound I. Significance of the pyrrole-β-substituted structure of the hemes in native enzymes is also discussed on the basis of this study.

Manganese(Ⅲ)-iodosylbenzene complex, preparation method thereof and oxidant comprising the same

-

Paragraph 0130-0136; 0141; 0166, (2020/09/22)

The present invention relates to a manganese(III)-iodosylbenzene complex, a preparation method thereof, and an oxidant comprising the same. The manganese(III)-iodosylbenzene complex provided in one aspect of the present invention has an effect of inducing a hydrogen atom abstraction (HAA) reaction of cyclohexadiene, dihydroanthracene and xanthine, and an oxygen atom transfer (OAT) reaction of thioanisole and stilbene with excellent electrophilic reactivity. The manganese(III)-iodosylbenzene complex is represented by a compound of formula 1: [Mn^III(L)(OIPh)(OH)]^2+.COPYRIGHT KIPO 2020

Asymmetric synthesis of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives proper for solid-phase peptide coupling

Tokairin, Yoshinori,Soloshonok, Vadim A.,Moriwaki, Hiroki,Konno, Hiroyuki

, p. 419 - 432 (2018/11/27)

Practical new routes for preparation of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives, the key structural components of cytotoxic marine peptides callipeltin O and Q, suitable for the Fmoc-SPPS, were developed. (2S,3S)-Fmoc-3-Me-Gln(Xan)-OH was synthesized via Michael addition reactions of Ni (II) complex of chiral Gly-Schiff base; while Fmoc-(R)-allo-Thr-OH was prepared using chiral Ni (II) complex-assisted α-epimerization methodology, starting form (S)-Thr(tBu)-OH.

CoI-Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines

Presset, Marc,Paul, Jér?me,Cherif, Ghania Nait,Ratnam, Nisanthan,Laloi, Nicolas,Léonel, Eric,Gosmini, Corinne,Le Gall, Erwan

supporting information, p. 4491 - 4495 (2019/02/27)

The reductive Barbier coupling of aromatic halides and electrophiles has been achieved using a CoBr2/1,10-phenanthroline catalytic system and over stoichiometric amounts of zinc. The reaction displayed a broad scope of substrates, including (hetero)aryl chlorides as pro-nucleophiles and aldehydes or imines as electrophiles, leading to diarylmethanols and diarylmethylamines in moderate to excellent yields, respectively.

Preparation method of xanthydrol

-

Paragraph 0008; 0009, (2018/03/26)

The invention relates to the chemical field, in particular to a preparation method of xanthydrol. The method comprises the steps as follows: 31.3 g of o-chlorobenzoic acid, 37.6 g of phenol, 5.53 g ofpotassium carbonate, 16.2 mL of pyridine, 2 g of copper powder, 2 g of cuprous iodide and 200 mL of water are added to a 500 mL three-neck flask, the mixture is stirred mechanically, subjected to reflux for 2 h and cooled to the room temperature, diluted hydrochloric acid is added to make a reaction solution to be acid, a solid is filtered out, washed and dissolved in a 10% sodium hydroxide aqueous solution, the obtained solution is added to a mixed solution of acetic acid and water for precipitation of a solid, the obtained solid is recrystallized with the mixed solution of acetic acid and water, and 36.4 g of white crystal o-phenoxybenzoic acid is obtained; 20 g of o-phenoxybenzoic acid and 80 mL of tetrahydrofuran are added to a 150 mL three-neck flask, the mixture is stirred mechanically and cooled to 0 DEG C, 23 mL of a catalyst is dropwise added at the temperature of 0 DEG C, the obtained mixture is heated for reflux for 30 min after addition and cooled to the room temperature,and ice water is added to a reaction solution. The technological process is simple and safe to operate, the production cost is reduced, environmental pollution is avoided in the reaction process, andthe product quality is improved.

Process route upstream and downstream products

Process route

hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

(2-nitro-phenyl)-xanthen-9-yl-amine
6630-79-1

(2-nitro-phenyl)-xanthen-9-yl-amine

9-hydroxyxanthene
90-46-0

9-hydroxyxanthene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
Conditions Yield
xanth-9-one
90-47-1

xanth-9-one

9-hydroxyxanthene
90-46-0

9-hydroxyxanthene

Conditions
Conditions Yield
With tetrabutylammomium bromide; zinc(II) cation; In N,N-dimethyl-formamide; Ambient temperature; electrolysis;
100%
With ethanol; sodium hydroxide; zinc; at 20 ℃; for 4h; Concentration; Reflux;
94%
With methanol; potassium hydroxide; aluminium; for 0.5h; Ambient temperature;
92%
With sodium tetrahydroborate; In ethanol; at 20 ℃;
92%
With chromium chloride; tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 20 ℃; electrolysis;
90%
With chromium (III) ion; tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 20 ℃;
90%
With methanol; sodium tetrahydroborate;
82%
With acridine; acetic acid; for 4h; Heating;
65%
With sodium hydroxide; ethanol; zinc; Wasser;
With sodium amalgam; ethanol;
With sodium amalgam; ethanol;
With aluminum isopropoxide; isopropyl alcohol;
With lithium aluminium tetrahydride; diethyl ether;
With sodium hexachloroplatinate; nickel; Hydrogenation;
With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃;
With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;
With acetate-phosphate-borate buffer; tetramethylammonium bromide; In ethanol; for 2h; Mechanism; polarographic reduction;
With sodium tetrahydroborate; In water;
With lithium aluminium tetrahydride; In diethyl ether;
With lithium aluminium tetrahydride; In diethyl ether;
With sodium tetrahydroborate; In ethanol; at 20 ℃; for 4h; Inert atmosphere;
With sodium tetrahydroborate; In methanol;
With sodium tetrahydroborate; In methanol; at 20 ℃; for 24.3h;
With sodium hydroxide; zinc; In ethanol; for 2h; Reflux;
9.5 g
xanthene
92-83-1

xanthene

9-hydroxyxanthene
90-46-0

9-hydroxyxanthene

xanth-9-one
90-47-1

xanth-9-one

Conditions
Conditions Yield
With [5,10,15,20-tetrakis-1-methyl-4-pyridylporphyrinate iron(III) tetrachloride salt]chloride; 3-chloro-benzenecarboperoxoic acid; In acetonitrile; at 20 ℃; pH=4.7; aq. acetate buffer;
90%
With [MnIV(N,N'-di-tert-butyl-2,11-diaza[3.3](2,6)-pyridinophane)(OIPh)(OH)]2+; In 2,2,2-trifluoroethanol; acetonitrile; at 20 ℃; Kinetics;
51%
13%
With oxygen; ozone; In dichloromethane; at 0 ℃; for 0.0666667h; Product distribution; var. solvents (CHCl3, CCl4), presence of singlet oxygen acceptor (1,3-diphenylisobenzofuran, tetraphenylcyclopentadiene ) at -78 deg C;
4 % Turnov.
74 % Turnov.
With Fe(4+)*O(2-)*NO3(1-)*C56H52N4(1-); In dichloromethane; at -30 ℃; Temperature; Reagent/catalyst; Kinetics; Catalytic behavior; Schlenk technique;
75 %Spectr.
10 %Spectr.
With iodosylbenzene; [MnII(N,N′-di-tert-butyl-2,11-diaza[3.3](2,6)-pyridinophane)(triflato)2]; In 2,2,2-trifluoroethanol; acetonitrile; at 20 ℃; Kinetics;
51 %Chromat.
13 %Chromat.
salicylaldehyde
90-02-8

salicylaldehyde

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

9-hydroxyxanthene
90-46-0

9-hydroxyxanthene

Conditions
Conditions Yield
With potassium carbonate; cesium fluoride; In acetonitrile; at 20 ℃; for 15h;
91%
xanth-9-one
90-47-1

xanth-9-one

9-hydroxyxanthene
90-46-0

9-hydroxyxanthene

xanthene
92-83-1

xanthene

Conditions
Conditions Yield
With potassium hydroxide; zinc; In dimethyl sulfoxide; at 30 ℃;
37%
58.5%
With potassium hydroxide; zinc; In dimethyl sulfoxide; at 30 ℃;
58%
37.5%
With iodine; magnesium; In methanol; at 20 ℃; for 2.5h;
33%
22%
With sodium tetrahydroborate; nickel dichloride; In tetrahydrofuran; at 20 ℃; for 4h;
32%
xanthene
92-83-1

xanthene

9-hydroxyxanthene
90-46-0

9-hydroxyxanthene

C<sub>13</sub>H<sub>10</sub>O<sup>(18)</sup>O

C13H10O(18)O

Conditions
Conditions Yield
With [5,10,15,20-tetrakis-1-methyl-4-pyridylporphyrinate iron(III) tetrachloride salt]chloride; 18O-labeled water; 3-chloro-benzenecarboperoxoic acid; In acetonitrile; at 20 ℃; pH=4.7; aq. acetate buffer;
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

N,N-dimethyl-formamide
68-12-2,33513-42-7

N,N-dimethyl-formamide

9-hydroxyxanthene
90-46-0

9-hydroxyxanthene

Conditions
Conditions Yield
With potassium carbonate; cesium fluoride; In acetonitrile; at 20 ℃; for 14h;
52%
xanthene
92-83-1

xanthene

9-hydroxyxanthene
90-46-0

9-hydroxyxanthene

9H-xanthen-2-ol
30414-78-9

9H-xanthen-2-ol

xanth-9-one
90-47-1

xanth-9-one

Conditions
Conditions Yield
With perchloric acid; 4C16H36N(1+)*HO40PV2W10(4-); dihydrogen peroxide; In water; acetonitrile; tert-butyl alcohol; at 59.84 ℃; for 1h; under 760.051 Torr; chemoselective reaction; Inert atmosphere;
2-(2-bromophenoxy)benzaldehyde
1020959-71-0

2-(2-bromophenoxy)benzaldehyde

9-hydroxyxanthene
90-46-0

9-hydroxyxanthene

xanth-9-one
90-47-1

xanth-9-one

Conditions
Conditions Yield
With 1,10-Phenanthroline; 3-chloroprop-1-ene; trifluoroacetic acid; cobalt(II) bromide; zinc; In acetonitrile; at 80 ℃; for 16h; Inert atmosphere; Sealed tube;
30%
18%
xanthene
92-83-1

xanthene

9-hydroxyxanthene
90-46-0

9-hydroxyxanthene

Conditions
Conditions Yield
With [5,10,15,20-tetrakis-1-methyl-4-pyridylporphyrinate iron(III) tetrachloride salt]chloride; 3-chloro-benzenecarboperoxoic acid; In acetonitrile; at 14.5 ℃; pH=4.7; Kinetics; aq. acetate buffer;
With Fe(4+)*O(2-)*NO3(1-)*C56H52N4(1-)*C3H4N2; In dichloromethane; at -60 ℃; Temperature; Kinetics; Catalytic behavior; Schlenk technique;
97 %Spectr.

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