Conditions | Yield |
---|---|
With molybdenum trisulfide; hydrogen In octane at 240℃; under 75006 Torr; for 1.5h; | 98% |
Stage #1: xanth-9-one With aluminum (III) chloride; lithium aluminium tetrahydride Stage #2: Acidic conditions; | 94% |
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 23 - 60℃; for 3h; Solvent; Temperature; Inert atmosphere; | 90% |
9-hydroxyxanthene
aniline
A
xanthene
B
xanth-9-one
C
phenyl-xanthen-9-yl-amine
Conditions | Yield |
---|---|
methyltrioxorhenium(VII) In benzene for 48h; Ambient temperature; | A n/a B n/a C 96% |
Conditions | Yield |
---|---|
With phenylphosphane at 140℃; for 10h; | 93% |
With disodium telluride In tetrahydrofuran; N,N-dimethyl-formamide for 48h; Heating; | 82% |
With diphosphorus tetraiodide In benzene for 9h; Heating; | 56% |
2-(phenoxy)benzaldehyde
xanthene
Conditions | Yield |
---|---|
With indium(III) triflate In di-isopropyl ether at 95℃; for 24h; Inert atmosphere; Sealed tube; | 86% |
With titanium tetrachloride In dichloromethane at 20℃; for 24h; | 85% |
xanthene
Conditions | Yield |
---|---|
With water; copper diacetate; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 12h; Inert atmosphere; Sealed tube; | 85% |
Conditions | Yield |
---|---|
With Nafion-H; toluene for 24h; Heating; | A n/a B 80% |
Conditions | Yield |
---|---|
With manganese triacetate In acetic acid for 2h; Heating; | A 17% B 73% |
With iodine In acetonitrile at 20℃; for 0.0833333h; | A 43% B 42% |
With 2-oxoindole; 1,3-dichloro-1,1,3,3-tetrabutylstannoxane In dichloromethane at 20℃; for 10h; | A 42% B 13% |
9-hydroxyxanthene
tert.-butylhydroperoxide
A
xanthene
B
xanth-9-one
C
(tert-butyl)xanthyl peroxy-ether
D
dixanthyl ether
Conditions | Yield |
---|---|
With 2-Picolinic acid In pyridine; acetic acid at 20℃; for 1h; Title compound not separated from byproducts; | A 22% B 66% C 34% D 18% |
9-hydroxyxanthene
A
xanthene
B
xanth-9-one
C
(tert-butyl)xanthyl peroxy-ether
D
dixanthyl ether
Conditions | Yield |
---|---|
With 2-Picolinic acid; tert.-butylhydroperoxide In pyridine; acetic acid at 20℃; for 1h; Title compound not separated from byproducts; | A 22% B 66% C 34% D 18% |
Conditions | Yield |
---|---|
platinum on activated charcoal at 340 - 360℃; | A 65% B 3.6% |
4-morpholinecarboxaldehyde
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
A
xanthene
B
xanth-9-one
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile at 20℃; for 14h; | A 15% B 23% C 62% |
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
N,N-dimethyl-formamide
A
xanthene
B
xanth-9-one
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile at 20℃; for 13h; | A 16% B 24% C 62% |
Conditions | Yield |
---|---|
With 1,3-benzodithiole In tetrahydrofuran at 80℃; | 60% |
With N-ethyl-N,N-diisopropylamine In pyridine for 1h; Heating; | 57% |
With N-ethyl-N,N-diisopropylamine Mechanism; | |
Multi-step reaction with 2 steps 2: 56 percent / diisopropylethylamine / pyridine / 1 h / Heating View Scheme | |
With isopropyl alcohol In acetonitrile at 60℃; Kinetics; Reagent/catalyst; |
Conditions | Yield |
---|---|
With aluminium trichloride; toluene for 12h; Ambient temperature; | A 60% B 25% |
N,N-dimethylthioformamide
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
A
xanthene
B
xanth-9-one
C
diphenyl sulfide
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile at 20℃; for 13h; | A 10% B 12% C 60% D 60% |
9-hydroxyxanthene
3-phenyloxindole
A
xanthene
B
xanth-9-one
Conditions | Yield |
---|---|
With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea In dichloromethane at 20℃; for 24h; Reagent/catalyst; | A n/a B n/a C 59% |
Conditions | Yield |
---|---|
With potassium hydroxide; zinc In dimethyl sulfoxide at 30℃; | A 58.5% B 37% |
With potassium hydroxide; zinc In dimethyl sulfoxide at 30℃; | A 58% B 37.5% |
With iodine; magnesium In methanol at 20℃; for 2.5h; | A 33% B 22% |
With sodium tetrahydroborate; nickel dichloride In tetrahydrofuran at 20℃; for 4h; | A n/a B 32% |
(9H-xanthene-9-yl) triphenyl phosphonium perchlorate
xanthene
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In pyridine for 1h; Heating; | 56% |
Conditions | Yield |
---|---|
With scandium tris(trifluoromethanesulfonate) In chlorobenzene at 180℃; for 0.5h; Microwave irradiation; | 56% |
Conditions | Yield |
---|---|
With gallium(III) triflate; isopropyl alcohol for 12h; Glovebox; Reflux; | 54% |
With iodine; magnesium In methanol at 20℃; for 0.75h; |
1,1-Diphenylethylene
monomethyl 2-(9-xanthenyl)malonate
A
xanthene
B
xanth-9-one
C
2-methoxycarbonyl-4,4-diphenyl-2-(9-xanthenyl)-4-butanolide
D
10-(methoxycarbonyl)dibenzoxepin
Conditions | Yield |
---|---|
With manganese triacetate In acetic acid for 0.166667h; Reflux; | A 5% B 12% C 31% D 51% |
Spiro
A
3,4-dimethylthiophene
B
xanthene
C
2,3-Dimethyl-2-butene
D
9H-xanthene-9-thione
E
9,9'-bixanthene
F
2,3-dimethyl-buta-1,3-diene
Conditions | Yield |
---|---|
at 240 - 260℃; for 0.333333h; Product distribution; | A 23 % Spectr. B 25% C 8 % Spectr. D 50% E 18% F 26 % Spectr. |
Spiro
A
xanthene
B
9H-xanthene-9-thione
C
9,9'-bixanthene
D
2,3-dimethyl-buta-1,3-diene
Conditions | Yield |
---|---|
at 240 - 260℃; for 0.333333h; Further byproducts given; | A 25% B 50% C 18% D 26 % Spectr. |
Conditions | Yield |
---|---|
With 1-Benzyl-1,4-dihydronicotinamide In water; acetonitrile at 25℃; Kinetics; Thermodynamic data; Mechanism; pH=6.90, ionic strength of 1.0; ΔH(excit.), ΔS(excit.); various reagents are used; | 50% |
With potassium chloride; 1,4-dihydropyridine-1-phenyl-3-carboxamide In phosphate buffer; acetonitrile at 25℃; pH=6.90; Kinetics; Further Variations:; Reagents; | |
With 1,4-dihydropyridine-1-phenyl-3-carboxamide In water; acetonitrile at 20℃; for 16h; |
monomethyl 2-(9-xanthenyl)malonate
A
xanthene
B
xanth-9-one
C
10-(methoxycarbonyl)dibenzoxepin
Conditions | Yield |
---|---|
With water; manganese triacetate; copper(ll) bromide In acetic acid for 0.0833333h; Reflux; | A 23% B 25% C 49% |
salicylaldehyde
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
A
xanthene
B
xanth-9-one
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile at 20℃; for 15h; | A 42% B 46% |
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at 20℃; for 24h; | A 42% B 45.4% |
7-(4-Aminophenyl)-1,3,5-cycloheptatrien
Xanthylium perchlorate
A
xanthene
Conditions | Yield |
---|---|
With 1H-imidazole In tetrahydrofuran at 20℃; for 2.5h; | A n/a B 44% |
Spiro
A
3,4-dimethylthiophene
B
xanthene
C
9,9'-bixanthene
D
3,4-Dimethyl-2-(9'-xanthenyl)thiophen
Conditions | Yield |
---|---|
In benzene for 10h; Product distribution; Heating; | A n/a B n/a C n/a D 38% |
In benzene for 10h; Heating; | A n/a B n/a C n/a D 38% |
2-hydroxytricyclo[7.3.1.02.7]tridecan-13-one
A
xanthene
B
o-Benzylphenol
Conditions | Yield |
---|---|
platinum on activated charcoal at 280 - 300℃; | A 32% B 35% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; pentafluorobenzeneseleninic acid In benzene for 4h; Heating; | 100% |
With aluminum oxide; potassium permanganate at 120℃; for 0.2h; Irradiation; | 100% |
With potassium permanganate; manganese(II) sulfate In dichloromethane at 20℃; for 24h; | 100% |
xanthene
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran for 0.05h; Ambient temperature; | 99% |
xanthene
1-ethyl-4-phenylquinazolin-2(1H)-one
1-Ethyl-4-phenyl-4-(9H-xanthen-9-yl)-3,4-dihydro-1H-quinazolin-2-one
Conditions | Yield |
---|---|
In benzene for 15h; Ambient temperature; Irradiation; | 99% |
Conditions | Yield |
---|---|
Stage #1: xanthene With n-butyllithium at -50℃; Stage #2: cyclohexanecarbaldehyde | 99% |
Conditions | Yield |
---|---|
With KN(SiMe3)2; palladium diacetate; nixantphos In cyclopentyl methyl ether at 24℃; for 12h; Inert atmosphere; | 99% |
With bis(1,5-cyclooctadiene)nickel (0); sodium hexamethyldisilazane; nixantphos at 110℃; for 16h; | 81% |
xanthene
cis-2,3-diphenyl-N-benzenesulphonylaziridine
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran for 0.0833333h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With methanesulfonic acid; tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 2h; Electrochemical reaction; | 98% |
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere; | 97% |
xanthene
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With dibenzoyl peroxide In 1,2-dichloro-ethane at 80℃; for 6h; Schlenk technique; | 97% |
With tetrabutylammonium perchlorate In acetonitrile at 23℃; for 2.9h; Electrochemical reaction; | 94% |
1,2,3-Benzotriazole
xanthene
1-(9H-xanthen-9-yl)-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With dibenzoyl peroxide In 1,2-dichloro-ethane at 80℃; for 6h; Mechanism; Reagent/catalyst; Solvent; Temperature; Schlenk technique; | 96% |
With tetrabutylammonium perchlorate In acetonitrile at 23℃; for 3.1h; Electrochemical reaction; | 78% |
With methanesulfonic acid; tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 2h; Electrochemical reaction; | 72% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 2h; Heating; | 20% |
xanthene
1-cinnamoyl-2,2-dimethylaziridine
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran for 24h; Ambient temperature; | 96% |
xanthene
1-methyl-4-phenyl-1,2-dihydroquinazol-2-one
1-Methyl-4-phenyl-4-(9H-xanthen-9-yl)-3,4-dihydro-1H-quinazolin-2-one
Conditions | Yield |
---|---|
In benzene Product distribution; Mechanism; Ambient temperature; Irradiation; other hydrogen donors; other solvents and reaction time; also with addition of t-stilbene; | 96% |
In benzene for 15h; Ambient temperature; Irradiation; | 96% |
xanthene
diethyl malonate
9-(1'-ethoxycarbonyl-2'-oxo-3'-oxapent-1'-yl)xanthene
Conditions | Yield |
---|---|
With oxygen at 25℃; for 12h; Irradiation; | 96% |
With trifluorormethanesulfonic acid; oxygen In dichloromethane at 20 - 25℃; under 45004.5 Torr; for 64h; Autoclave; | 39% |
With trifluorormethanesulfonic acid; oxygen In dichloromethane at 20 - 25℃; under 45004.5 Torr; for 144h; | 39% |
1,2,3-trimethoxybenzene
xanthene
9-(2',4',6'-trimethoxyphenyl)-9H-xanthene
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; methanesulfonic acid In decane; acetone at 40℃; for 18h; Solvent; | 96% |
With trifluorormethanesulfonic acid; oxygen In dichloromethane at 70℃; under 75007.5 Torr; for 24h; | 80% |
With palladium diacetate; copper(II) bis(trifluoromethanesulfonate) at 130℃; for 3h; | 45% |
Conditions | Yield |
---|---|
With palladium diacetate; trifluoroacetic acid at 20℃; for 0.75h; | 96% |
Conditions | Yield |
---|---|
With air In ethanol at 20℃; for 24h; Green chemistry; | 96% |
With air In ethanol at 20℃; for 24h; Schlenk technique; | 96% |
4-ethoxycarbonylpyrazole
xanthene
Conditions | Yield |
---|---|
With dibenzoyl peroxide In 1,2-dichloro-ethane at 80℃; for 6h; Schlenk technique; | 96% |
Conditions | Yield |
---|---|
With aluminium trichloride In 1,2-dichloro-ethane for 3h; Ambient temperature; | 95% |
With carbon disulfide; aluminium trichloride |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane for 2h; Ambient temperature; | 95% |
With n-butyllithium In diethyl ether | 81% |
Stage #1: xanthene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran for 3h; Inert atmosphere; | 70% |
Conditions | Yield |
---|---|
Stage #1: xanthene With n-butyllithium at 20℃; for 1h; Stage #2: trimethylene oxide | 95% |
Conditions | Yield |
---|---|
With methanesulfonic acid; oxygen at 40℃; under 750.075 Torr; for 5h; Neat (no solvent); Sealed vial; | 95% |
xanthene
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With air In ethanol at 20℃; for 24h; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With air In ethanol at 20℃; for 24h; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With dibenzoyl peroxide In 1,2-dichloro-ethane at 80℃; for 6h; Schlenk technique; | 95% |
xanthene
2,7-dibromo-9H-xanthene
Conditions | Yield |
---|---|
With bromine; acetic anhydride; acetic acid at 20℃; for 2h; Inert atmosphere; Cooling with ice; | 94% |
With bromine In chloroform | 38.1% |
Conditions | Yield |
---|---|
With methanesulfonic acid; oxygen at 40℃; under 750.075 Torr; for 36h; Neat (no solvent); Sealed vial; | 94% |
With oxygen at 40℃; for 24h; Sealed tube; | 91% |
With oxygen at 25℃; for 3h; Reagent/catalyst; Wavelength; Temperature; Irradiation; | 91% |
With methanesulfonic acid; tetrabutylammonium tetrafluoroborate In methanol; acetonitrile at 20℃; for 2h; Electrochemical reaction; | 68% |
Chemistry informtion about Xanthene (CAS NO.92-83-1) is:
IUPAC Name: 9H-xanthene
Synonyms: 10h-9-Oxaanthracene ; 9h-Xanthene ; Dibenzo[A,E]Pyran ; Dibenzopyran, Tricyclic ; Xanthane ; Dibenzopyran ; Xanthan ; Xanthene
MF: C13H10O
MW: 182.22
EINECS: 202-194-4
Melting Point: 101-102 °C(lit.)
Density: 1.159 g/cm3
Flash Point: 137.5 °C
Boiling Point: 311 °C at 760 mmHg
Vapour Pressure: 0.00106 mmHg at 25°C
Enthalpy of Vaporization: 52.99 kJ/mol
Water Solubility: Soluble
Stability: Stable, Combustible,Incompatible with oxidizing agents.
Following is the molecular structure of Xanthene (CAS NO.92-83-1) is:
Xanthene (CAS NO.92-83-1) is used as a fungicide and it is also a useful intermediate in organic synthesis.
Preparation Products: Xanthene-9-Carboxylic Acid
Raw Materials: Sodium Hydroxide→Diethyl Ether→Phenol→Phosphorus Pentoxide→2-Hydroxybenzyl Alcohol
1. | scu-mus LD50:690 mg/kg | ARZNAD Arzneimittel-Forschung. Drug Research. 8 (1958),107. |
Reported in EPA TSCA Inventory.
Moderately toxic by subcutaneous route. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:
Xn: Harmful
Risk Statements:
R42/43: May cause sensitization by inhalation and skin contact.
Safety Statements:
S22: Do not breathe dust.
S36/37: Wear suitable protective clothing and gloves.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S24: Avoid contact with skin.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 3
RTECS: ZD5520000
HS Code: 29181100
Xanthene (CAS NO.92-83-1) is a yellow organic heterocyclic compound.
First Aid Measures:
Ingestion: If victim is conscious and alert, give 2-4 cupfuls of milk or water. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. May cause digestive tract disturbances. Seek medical assistance.
Inhalation: Move victim to fresh air. Apply artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. May cause respiratory tract irritation. Get medical aid immediately. Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Skin: Remove and isolate contaminated clothing and shoes. Immediately flush with running water for at least 20 minutes. Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Remove contaminated clothing and shoes. May cause skin irritation.
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately. Immediately flush with running water for at least 20 minutes. May cause eye irritation.
Handling and Storage:
Storage: Keep away from heat, sparks, and flame. Store in a cool, dry, well-ventilated area away from incompatible substances. Flammables-area. Keep containers tightly closed.
Handling: Ground and bond containers when transferring material. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Avoid contact with heat, sparks and flame. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
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