1,2,3,4-tetrahydroxy-1β,2α,3α,4β,4aβ,9α,9aβ,10α-hexahydro-9,10<1',2'>benzenoanthracene
A
anthracene
B
conduritol A
Conditions | Yield |
---|---|
at 460℃; under 0.1 Torr; for 0.5h; | A 100% B 100% |
2,3-dihydroxy-1,4-dimethoxy-1β,2α, 3α,4β,4aβ,9α,9aβ,10α-octahydro-9,10<1',2'>benzenoanthracene
A
anthracene
B
<1α,2α,3β,6β>-3,6-dimethoxycyclohex-4-ene-1,2-diol
Conditions | Yield |
---|---|
at 440℃; under 0.05 Torr; for 2h; | A 100% B 99% |
Conditions | Yield |
---|---|
at 651.9℃; under 1E-06 Torr; sublimation through a short path flash vacuum pyrolysis (fvp) oven; | A n/a B 100% C n/a |
Conditions | Yield |
---|---|
at 651.9℃; under 1E-06 Torr; sublimation through a short path flash vacuum pyrolysis (fvp) oven; | A n/a B 100% C n/a |
Conditions | Yield |
---|---|
at 600℃; under 0.06 Torr; | A n/a B 100% |
2-benzylbenzaldehyde
anthracene
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; toluene-4-sulfonamide In toluene at 20℃; for 0.166667h; | 100% |
With boron trifluoride diethyl etherate; toluene-4-sulfonamide In toluene at 20℃; for 0.166667h; | 99% |
With indium(III) triflate In 1,2-dichloro-ethane at 115℃; for 6h; Inert atmosphere; | 94% |
C14H10Yb
anthracene
Conditions | Yield |
---|---|
With oxygen In 1,2-dimethoxyethane addn. of dry oxygen to a suspension of Yb complex; | 100% |
anthracene
Conditions | Yield |
---|---|
With oxygen In 1,2-dimethoxyethane addn. of dry oxygen to a suspension of Sm complex; | 100% |
Conditions | Yield |
---|---|
With sulfuric acid; dinitrogen monoxide; Ru(5,10,15,20-tetramesitylporphyrin)(O)2 In benzene at 120℃; under 7600 Torr; for 4h; | 99% |
With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In toluene at 120℃; under 9750.98 Torr; for 8h; | 99% |
With C64H50F8N6Ru In dichloromethane-d2 at 20℃; Reagent/catalyst; Schlenk technique; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With SmI2(hmpa)4 In tetrahydrofuran at 20℃; for 0.0166667h; | 99% |
With potassium tert-butylate; N,N-dimethyl-formamide at 35℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation; | 70% |
With triethylamine In acetonitrile Product distribution; Quantum yield; Mechanism; Ambient temperature; Irradiation; quenching rate constants by azulene, ferrocene, and amines, decay rate constants of the radical anion; | |
With tetraethylammonium perchlorate In acetonitrile at 24.99℃; Electrochemical reaction; |
Conditions | Yield |
---|---|
With 2-H-1,3-di-tert-butyl-1,3,2-diazaphosphorinane; 2,2'-azobis(isobutyronitrile) In toluene at 90℃; for 5h; | 99% |
With 1,3-bis(2,6-diisopropylphenyl)-2,4-diphenylimidazole In N,N-dimethyl-formamide at 20℃; for 36h; Glovebox; | 98% |
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 96% |
A
anthracene
Conditions | Yield |
---|---|
at 440℃; | A 99% B 95% |
anthracene-9-boronic acid
anthracene
Conditions | Yield |
---|---|
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); water In toluene at 90℃; for 2h; Microwave irradiation; Green chemistry; | 99% |
With acetic acid at 130℃; for 3h; Green chemistry; | 92% |
With sodium hypochlorite; tetrabutylammomium bromide; water at 100℃; | 91% |
With copper(l) chloride In methanol at 25℃; for 3h; |
1,2,3,4-tetramethoxy-1β,2α, 3α,4β,4aβ,9α,9aβ,10α-octahydro-9,10<1',2'>benzenoanthracene
A
anthracene
B
3α,4β,5β,6α-tetramethoxycyclohex-4-ene-1α,2α-diol
Conditions | Yield |
---|---|
at 410℃; under 0.03 Torr; for 1.5h; | A 57 mg B 98% |
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate In ethyl acetate at 150℃; under 12929 Torr; for 0.833333h; Microwave irradiation; Molecular sieve; | 98% |
With palladium nanoparticles supported on fibrous silica In cyclohexane at 130℃; for 20h; Molecular sieve; | 98% |
With palladium diacetate In cyclohexane at 140℃; for 24h; Molecular sieve; air; | 97% |
9,10-dihydroanthracene
A
[(1,10-phenanthroline)2Mn(η1-OClO3)2]
B
anthracene
C
anthracen-9(10H)-one
D
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
In acetonitrile Kinetics; the soln. in acetonitrile was allowed to stand overnight at room temp.; the organic products were detected by GC/MS; the soln. was layered with ether; | A n/a B 97% C 0.8% D 2% |
anthracene
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 0 - 20℃; for 1h; | 97% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; H5PV2Mo10O40(1,11) In toluene for 24h; Ambient temperature; | A 96% B 4% |
With dinitrogen monoxide; Ru(5,10,15,20-tetramesitylporphyrin)(O)2 In benzene at 200℃; under 7600 Torr; for 20h; Product distribution; Further Variations:; Solvents; Reagents; Temperatures; | A 9% B 90% |
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In benzene at 200℃; under 7600 Torr; for 20h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures; | A 9% B 90% |
Conditions | Yield |
---|---|
aluminum oxide In isopropyl alcohol at 400℃; benzene as solvent; | 95% |
With iodine; magnesium In methanol at 20℃; for 3.5h; | 94% |
With sulfur In isopropyl alcohol at 400℃; for 5h; | 90% |
Conditions | Yield |
---|---|
With nickel(II) acetate tetrahydrate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 170℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; | 95% |
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triisopropyl phosphite; chlorotriisopropylsilane In toluene at 160℃; for 15h; Inert atmosphere; | 94% |
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triisopropyl phosphite; chlorotriisopropylsilane In toluene at 160℃; for 15h; Inert atmosphere; | 94% |
Multi-step reaction with 2 steps 1: 12 percent / NH4Cl, NaN3 / dimethylformamide / 360 h / 90 °C 2: 9 percent / 600 °C / 0 - 0.1 Torr View Scheme | |
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; ethanol; potassium hexamethylsilazane In toluene at 150℃; for 8h; Inert atmosphere; | 62 %Spectr. |
9-chloroanthracene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
anthracene
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); lithium chloride In toluene at 100℃; for 15h; | 94% |
9,10-dihydro-9,10-(2-phenyl-1-thiaethano)anthracene
2,3-dimethyl-buta-1,3-diene
A
anthracene
B
3,4-dimethyl-6-phenyl-5,6-dihydro-2H-thiopyran
Conditions | Yield |
---|---|
In toluene at 98 - 99℃; for 1h; | A 92% B 92% |
Heating; | A 92% B 92% |
o-benzylbenzylidene chloride
anthracene
Conditions | Yield |
---|---|
at 475℃; under 0.1 Torr; flash vacuum pyrolysis; | 91% |
9,10-dihydroanthracen-9-ol
A
anthracene
B
anthracen-9(10H)-one
C
9,10-phenanthrenequinone
Conditions | Yield |
---|---|
With aluminum oxide; Ru(OH)x; oxygen In para-xylene at 129.85℃; under 760 Torr; for 0.166667h; | A 91% B 7% C 2% |
Conditions | Yield |
---|---|
With aluminum (III) chloride at 60℃; for 3.5h; | 90.3% |
With aluminium trichloride at 60℃; | |
With aluminium trichloride |
Conditions | Yield |
---|---|
at 575℃; under 0.1 Torr; flash vacuum pyrolysis; | 90% |
Conditions | Yield |
---|---|
With boron trifluoride In diethyl ether | A n/a B 90% |
(9,10-dihydro-9,10-anthracenylene)-3a,6a-(4,5-dihydro-1H,3H-thieno<3,4-c>thiophene)
A
anthracene
Conditions | Yield |
---|---|
at 700℃; under 0.001 Torr; | A 90% B 83% |
1,4-dihydro-1,4-epoxyanthracene
anthracene
Conditions | Yield |
---|---|
With triphenyl phosphite; ammonium perrhenate In toluene at 80℃; for 18h; Inert atmosphere; | 90% |
With isopropylmagnesium bromide In tetrahydrofuran for 2h; Heating; | 42% |
Multi-step reaction with 2 steps 1: 95 percent / Mg / 10percent Pd/C / methanol / 25 °C 2: HCl gas / ethanol / 2 h / Heating View Scheme |
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate; water; lithium cation In N,N-dimethyl-formamide cathodic reduction; | 100% |
With tetraethylammonium bromide In ethanol at 60℃; electrolysis, lead cathode; | 100% |
With tetrabutylammonium tetrafluoroborate; water; lithium cation In N,N-dimethyl-formamide Product distribution; cathodic reduction; other hydroxy compounds, other solvent; | 100% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 18h; Reagent/catalyst; Inert atmosphere; | 100% |
With Iodine monochloride In chloroform; acetonitrile for 3h; | 98.1% |
With N-chloro-succinimide; dimethyl sulfoxide In chloroform at 25℃; for 12h; Schlenk technique; | 75% |
Conditions | Yield |
---|---|
With bis(trifluoroacetoxy)iodobencene; trimethylsilyl bromide In dichloromethane at 20℃; Inert atmosphere; | 100% |
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide In dichloromethane at 25℃; for 0.583333h; | 98% |
With copper(ll) bromide In chloroform Reflux; | 94% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; lithium perchlorate; silica gel In dichloromethane at 20℃; for 0.0833333h; | 100% |
With oxygen; 1,2-dibromomethane at 20℃; for 2h; | 99% |
With N-Bromosuccinimide; lithium perchlorate; silica gel In dichloromethane for 0.5h; | 99% |
Conditions | Yield |
---|---|
With nicotinium dichromate In acetic acid for 0.75h; Heating; | 100% |
With potassium bromate In acetic acid Heating; | 100% |
With ruthenium trichloride; dihydrogen peroxide; acetic acid | 100% |
4-Phenyl-1,2,4-triazolidine-3,5-dione
anthracene
9,10-(4’-phenyl)urazolo-9,10-dihydroanthracene
Conditions | Yield |
---|---|
In toluene at 20℃; for 2h; | 100% |
In chloroform-d1 at 25℃; Equilibrium constant; Temperature; Diels-Alder reaction; Darkness; | 84 %Spectr. |
In chloroform at 24.84℃; Kinetics; Solvent; Diels-Alder Cycloaddition; |
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane for 1h; Ambient temperature; | 100% |
With aluminium trichloride In dichloromethane Diels-Alder reaction; | 87% |
With zinc(II) chloride for 4.5h; Diels-Alder Cycloaddition; Sealed tube; | 87% |
anthracene
(E)-But-2-enedioic acid methyl ester (1S,2R,3S,4R)-4,7,7-trimethyl-3-phenylcarbamoyloxy-bicyclo[2.2.1]hept-2-yl ester
C36H37NO6
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane at -30℃; for 24h; | 100% |
anthracene
Conditions | Yield |
---|---|
With oxygen; germanium hydride trichloride In benzene at 5℃; Product distribution; Mechanism; | 100% |
Conditions | Yield |
---|---|
In benzene Irradiation; | 100% |
Conditions | Yield |
---|---|
In dichloromethane for 0.5h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
In toluene for 4h; Diels-Alder Cycloaddition; Reflux; | 100% |
In toluene for 24h; Heating; | 36% |
Conditions | Yield |
---|---|
In dichloromethane for 4h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 20℃; for 0.5h; cycloaddition; elimination; | 100% |
Conditions | Yield |
---|---|
100% | |
100% |
Conditions | Yield |
---|---|
With C2H4I2 In 1,2-dimethoxyethane activation of Sm with C2H4I2 soln. (2h,room temp.) , flask cooled to -20°C and charged with anthracene , after 2h reaction time the flask was warmed to room temp. and the mixt. stirred overnight ; suspension; not isolated , GC anal.; | 100% |
Conditions | Yield |
---|---|
With C2H4I2 In 1,2-dimethoxyethane activation of Yb with C2H4I2 soln. (2h,room temp.) , flask cooled to -20°C and charged with anthracene , after 2h reaction time the flask was warmed to room temp. and the mixt. stirred overnight ; suspension; not isolated , GC anal.; | 100% |
anthracene
Conditions | Yield |
---|---|
In benzene-d6 at 70℃; for 1.16667h; Inert atmosphere; Schlenk technique; | 100% |
Conditions | Yield |
---|---|
at 20℃; for 0.0333333h; Diels-Alder Cycloaddition; | 100% |
(2,4-bis(2,6-diisopropylphenylimino)pentan-3-ide-.kappa2N,N')aluminum(I)
anthracene
Conditions | Yield |
---|---|
In benzene-d6 at 25 - 100℃; for 88h; Glovebox; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With C44H36B4F4N4O8S2 In dichloromethane at 20℃; for 12h; Reagent/catalyst; Inert atmosphere; Irradiation; | 100% |
The Molecular Structure of Anthracene (CAS NO.120-12-7):
Empirical Formula: C14H10
Molecular Weight: 178.2292
Nominal Mass: 178 Da
Average Mass: 178.2292 Da
Monoisotopic Mass: 178.07825 Da
Index of Refraction: 1.714
Molar Refractivity: 61.93 cm3
Molar Volume: 157.6 cm3
Surface Tension: 47.9 dyne/cm
Density: 1.13 g/cm3
Flash Point: 146.6 °C
Enthalpy of Vaporization: 55.76 kJ/mol
Boiling Point: 337.4 °C at 760 mmHg
Vapour Pressure: 0.000206 mmHg at 25°C
Appearance: Colourless Crystalline Solid
IUPAC Name: anthracene
Product Categories: Pharmaceutical Intermediates;Aromatic Compounds;Aromatics Compounds;Anthracenes;Highly Purified Reagents;Other Categories;Zone Refined Products;Aromatics;AM to AQAnalytical Standards;AromaticsChemical Class;Chemical Class;Hydrocarbons;NeatsAnalytical Standards;PAHs;ArenesEssential Chemicals;Reagent Plus;Routine Reagents;Arenes;Building Blocks;Organic Building Blocks;A;A-BAlphabetic;Alpha Sort;AM to AQ;Volatiles/ Semivolatiles;ArenesOrganic Electronics and Photonics;Light Emitters and Dopants;OLED and PLED Materials;DetectionSpectroscopy;Biochemicals and Reagents;Fluorescence/Luminescence;Fluorescent Probes, Labels, Particles and Stains;Luminescent Compounds/Detection;Scintillation reagents;Scintillation ReagentsBiochemicals and Reagents
Synonyms: Anthracene ; AI3-00155 ; ANTHRACENE ; Anthracen ; Anthracen [German] ; Bis-alkylamino anthracene ; CCRIS 767 ; EINECS 204-371-1 ; Green Oil ; HSDB 702 ; Paranaphthalene ; Tetra Olive N2G ; Anthracene ; Anthracene, pure ; Anthracene ; Anthracene oil (coal tar fraction) ; Coal tar pitch volatiles: anthracene
1. Anthracene (CAS NO.120-12-7) is used in the artificial production of the red dye alizarin. It is also used in wood preservatives, insecticides, and coating materials.
2. Anthracene (CAS NO.120-12-7) is an organic semiconductor. It is used as a scintillator for detectors of high energy photons, electrons and alpha particles. Plastics such as polyvinyltoluene can be doped with anthracene to produce a plastic scintillator that is approximately water equivalent for use in radiation therapy dosimetry.
1. | skn-mus 118 µg MLD | CALEDQ Cancer Letters (Shannon, Ireland). 4 (1978),333. | ||
2. | mma-sat 100 µg/plate ABCHA6 43,1433,79 | |||
3. | dns-hmn:fbr 10 mg/L | CNREA8 Cancer Research. 38 (1978),2091. | ||
4. | hma-mus/sat 125 mg/kg | JNCIAM Journal of the National Cancer Institute. 62 (1979),911. | ||
5. | dnd-mam:lym 100 µmol | BIPMAA Biopolymers. 9 (1970),689. | ||
6. | orl-mus LD:>17 g/kg | GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 13 (5)(1969),59. | ||
7. | ipr-mus LD50:430 mg/kg | PMRSDJ Progress in Mutation Research. 1 (1981),682. |
IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 56; Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 32 (1983),p. 105 ; Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 32 (1983),p. 105 . Reported in EPA TSCA Inventory. Community Right-To-Know List.
Hazard Codes: XiXnFTN
Risk Statements: 36/37/38-50/53-67-36-11-39/23/24/25-23/24/25-65-38
R36/37/38: Irritating to eyes, respiratory system and skin
R50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
R67: Vapours may cause drowsiness and dizziness
R36: Irritating to eyes
R11: Highly flammable
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed
R65: Harmful: may cause lung damage if swallowed
R38: Irritating to skin
Safety Statements: 26-60-61-24/25-16-9-45-36/37-62-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S60: This material and its container must be disposed of as hazardous waste
S61: Avoid release to the environment. Refer to special instructions / safety data sheets
S24/25: Avoid contact with skin and eyes
S16: Keep away from sources of ignition
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37: Wear suitable protective clothing and gloves
S62: If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label
S36: Wear suitable protective clothing
RIDADR: UN 3077 9/PG 3
WGK Germany: 2
HS Code: 29029010
Moderately toxic by intraperitoneal route. A skin irritant and allergen. Questionable carcinogen with experimental neoplastigenic and tumorigenic data. Combustible when exposed to heat, flame, or oxidizing materials. Moderately explosive when exposed to flame, Ca(OCl)2, chromic acid. To fight fire, use water, foam, CO2, water spray or mist, dry chemical. Explodes on contact with fluorine.
OSHA PEL: TWA 0.2 mg/m3
For occupational chemical analysis use OSHA: #ID-58 or NIOSH: Polynuclear Aromatic Hydrocarbons (HPLC), 5506; (GC), 5515.
1. Fire Fighting Measures
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. This material in sufficient quantity and reduced particle size is capable of creating a dust explosion.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
2. Handling and Storage
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Do not store in direct sunlight. Store in a tightly closed container.
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