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 N-Bromosuccinimide; C5H13NO3S In n-heptane at 25℃; for 19h; Reagent/catalyst; Darkness; | 85% |
With bis(trifluoroacetoxy)iodobencene; trimethylsilyl bromide In dichloromethane at 20℃; Inert atmosphere; | 83% |
With phosphorus pentabromide; benzene | |
With nitric acid; acetic acid | |
With 2,6-di-tert-butyl-pyridine; Bromoform In acetonitrile platinum mesh electrodes, H cell containing 0.1 M Bu4NPF6, constant current 10 mA; | 57 % Chromat. |
Conditions | Yield |
---|---|
With potassium permanganate; hydrogen bromide In acetonitrile | A 85% B 3% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; 2,4,6-trimethylaniline In dichloromethane at 0℃; for 8h; Inert atmosphere; regioselective reaction; | A 84% B 7% |
With N-Bromosuccinimide; C5H13NO3S In n-heptane at 60℃; for 4.5h; Darkness; | A 81% B 8% |
With N-Bromosuccinimide; iodine In tetrachloromethane Bromination; Heating; |
methanol
anthracene
A
trans-9,10-dihydro-9,10-dimethoxyanthracene
B
9,10-Dibromoanthracene
C
9-methoxyanthracene
D
9,10-dimethoxyanthracene
Conditions | Yield |
---|---|
With pyridine; bromine; sodium hydrogencarbonate; water at 20℃; for 0.25h; | A 82% B n/a C 1% D 1% |
Conditions | Yield |
---|---|
In dichloromethane for 24h; | 75% |
9-nitroanthracene
A
9,10-Dibromoanthracene
B
bromo-9 nitro-10 anthracene
Conditions | Yield |
---|---|
With bromine In nitromethane Heating; | A 22% B 44% |
9-anthracene aldehyde
A
9,10-Dibromoanthracene
B
9,10-bromoanthracene-9-carbaldehyde
Conditions | Yield |
---|---|
With bromine In tetrachloromethane at 0 - 5℃; for 20h; | A n/a B 22% |
9,10-dihydroanthracene
A
9,10-Dibromoanthracene
B
2,9,10-tribromo-anthracene
Conditions | Yield |
---|---|
With carbon disulfide; bromine; iodine Ausschluss von Licht; |
9,19-Dibromo-9,10-dihydroanthracene
9,10-Dibromoanthracene
diethyl ether
1,2,3,4,9,10-hexabromo-1,2,3,4-tetrahydro-anthracene
9,10-Dibromoanthracene
Conditions | Yield |
---|---|
Behandeln mit organischen Magnesiumverbindungen; β-form; |
Conditions | Yield |
---|---|
With tetrachloromethane; bromine |
Conditions | Yield |
---|---|
With bromine |
Conditions | Yield |
---|---|
With carbon disulfide; bromine at 20℃; |
1,2,3,4,9,10-hexabromo-1,2,3,4-tetrahydro-anthracene
benzene
9,10-Dibromoanthracene
Conditions | Yield |
---|---|
Einw. von Tageslicht; α-form; | |
bei Einw. von Sonnenlicht oder Quecksilber-Bogenlicht; α-form; |
Conditions | Yield |
---|---|
In diphenylether at 200℃; Rate constant; |
Conditions | Yield |
---|---|
With [76]fullerene In dichloromethane Rate constant; Ambient temperature; also with C78; |
9,10-epidioxy-9,10-dihydroanthracene
hydrogen bromide
9,10-Dibromoanthracene
Conditions | Yield |
---|---|
Je nach Konzentration; |
Conditions | Yield |
---|---|
at 260℃; |
tetrachloromethane
9-nitroanthracene
bromine
9,10-Dibromoanthracene
Conditions | Yield |
---|---|
at 75℃; |
9-Anthracenecarboxylic acid
bromine
A
9,10-Dibromoanthracene
B
10-bromo-9-anthracenecarboxylic acid
9-Bromoanthracene
nitric acid
acetic acid
A
9,10-Dibromoanthracene
B
9-nitroanthrone
9,10-Dibromoanthracene
Conditions | Yield |
---|---|
With acetic acid; zinc | |
With benzene Irradiation; | |
With zinc; benzene | |
With copper; benzene |
9,10-Dibromoanthracene
Conditions | Yield |
---|---|
With zinc; benzene | |
With copper; benzene | |
With acetic acid; zinc | |
durch Behandeln mit organischen Magnesiumverbindungen; |
carbon disulfide
9-benzylanthracene
bromine
9,10-Dibromoanthracene
Conditions | Yield |
---|---|
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) at 89℃; for 3h; | 100% |
With copper(l) iodide; C44H68N10*PdCl2; caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 5h; Sonogashira Cross-Coupling; Inert atmosphere; | 95% |
With potassium phosphate tribasic trihydrate; C50H40N6O2Pd(2+)*2F6P(1-); tetrabutylammomium bromide In 1,4-dioxane; water at 100℃; for 24h; Sonogashira Cross-Coupling; | 93% |
9,10-Dibromoanthracene
3-chlorophenylboronic acid
9,10-di(3-chlorophenyl)anthracene
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetra(n-butyl)ammonium hydroxide In 1,4-dioxane; water at 90℃; for 20h; Suzuki coupling; Inert atmosphere; | 100% |
9,10-Dibromoanthracene
4-methylphenylboronic acid
9,10-di-p-tolyl-anthracene
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 85℃; for 3h; Suzuki-Miyaura cross-coupling reaction; | 99% |
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 85℃; for 3h; Suzuki-Miyaura cross-coupling reaction; | 99% |
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate In water; toluene at 90℃; for 24h; Inert atmosphere; | 95% |
With tetrakis(triphenylphosphine) palladium(0); water; sodium carbonate In ethanol; toluene for 24h; Suzuki Coupling; Inert atmosphere; Reflux; | 89% |
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 24h; Suzuki coupling reaction; Heating; | 81% |
9,10-Dibromoanthracene
4-methoxyphenylboronic acid
9,10-bis-(4-methoxy-phenyl)-anthracene
Conditions | Yield |
---|---|
With water; palladium diacetate; cesium fluoride; cyclo-octa-1,5-diene; DavePhos In neat (no solvent) for 1.65h; Suzuki-Miyaura Coupling; Milling; Green chemistry; | 99% |
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene Suzuki-Miyaura cross-coupling reaction; Heating; | 95% |
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 85℃; for 7h; Suzuki-Miyaura cross-coupling reaction; | 95% |
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 85℃; for 10h; Suzuki-Miyaura cross-coupling reaction; | 99% |
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 85℃; for 11h; Suzuki-Miyaura cross-coupling reaction; | 99% |
9,10-Dibromoanthracene
4-formylphenylboronic acid,
4,4'-(anthracene-9,10-diyl)dibenzaldehyde
Conditions | Yield |
---|---|
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine In water at 20℃; for 0.166667h; Suzuki-Miyaura Coupling; Inert atmosphere; | 98.1% |
With dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; triethylamine In water at 20℃; for 12h; Suzuki-Miyaura Coupling; Green chemistry; | 95% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; benzene for 48h; Heating; | 78% |
9,10-Dibromoanthracene
tris-iso-propylsilyl acetylene
9,10-bis[(triisopropylsilanyl)ethynyl]-anthracene
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere; Reflux; | 98% |
With diethylamine; copper(l) iodide Sonogashira coupling; Heating; | 52% |
9,10-Dibromoanthracene
(3aR)-5,10-dibromo-2-(2,6-difluorophenyl)-3a,4,11,11a-tetrahydro-1H-4,11-ethenonaphtho[2,3-f]isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With aluminum (III) chloride In chloroform at 20℃; for 1h; Reagent/catalyst; Diels-Alder Cycloaddition; stereoselective reaction; | 98% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene for 5h; Inert atmosphere; Reflux; | 98% |
(4-(naphthalen-1-yl)phenyl)boronic acid
9,10-Dibromoanthracene
9-bromo-10-(4-(naphthalene-1-yl)phenyl)anthracene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 1.5h; Inert atmosphere; Reflux; | 97.5% |
Stage #1: (4-(naphthalen-1-yl)phenyl)boronic acid; 9,10-Dibromoanthracene With tetrakis(triphenylphosphine)palladium (0) In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #2: With potassium carbonate In tetrahydrofuran at 80℃; for 0.333333h; Inert atmosphere; |
Conditions | Yield |
---|---|
With tributyl-amine; PdCl2*4P(o-Tol)3; potassium carbonate In water at 100℃; for 3h; | 97% |
With C44H68N10*PdCl2; tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane at 110℃; for 6h; Heck Reaction; | 95% |
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; Heck Reaction; Green chemistry; | 90% |
With C50H40N6O2Pd(2+)*2F6P(1-); sodium acetate In 1,4-dioxane at 100℃; for 24h; Heck Reaction; | 86% |
styrene
9,10-Dibromoanthracene
A
(E,E)-9,10-Bis(styryl)anthracene
B
(Z,Z)-9,10-Bis(styryl)anthracene
Conditions | Yield |
---|---|
With dichlorobis(tri-O-tolylphosphine)palladium; tributyl-amine; potassium carbonate; tris-(o-tolyl)phosphine In water at 100℃; for 3h; | A 97% B n/a |
9,10-Dibromoanthracene
trimethylsilylacetylene
9,10-bis(trimethylsilyl)ethynylanthracene
Conditions | Yield |
---|---|
With copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride; diisopropylamine In tetrahydrofuran for 8h; Sonogashira coupling; Reflux; | 97% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran for 8h; Reflux; | 97% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine at 70℃; for 22h; Inert atmosphere; Reflux; | 95% |
Conditions | Yield |
---|---|
With potassium phosphate; dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium(II) In toluene at 80℃; for 0.0833333h; Suzuki-Miyaura cross-coupling reaction; Air; | 97% |
With potassium carbonate In methanol at 80℃; for 0.5h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; | 97% |
With potassium phosphate In ethanol at 80℃; for 2h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; | 97% |
4-morpholinecarboxaldehyde
9,10-Dibromoanthracene
9,10-diformylanthracene
Conditions | Yield |
---|---|
Stage #1: 9,10-Dibromoanthracene With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: 4-morpholinecarboxaldehyde In tetrahydrofuran at -78℃; | 97% |
tert-Butyl acrylate
9,10-Dibromoanthracene
di-tert-butyl 3,3'-(9,10-anthracenediyl)bis(2-propenoate)
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 120℃; for 4h; | 97% |
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 120℃; for 4h; | 97% |
9,10-Dibromoanthracene
3-fluorophenylboronic acid
9,10-di-(3-fluorophenyl)anthracene
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetra(n-butyl)ammonium hydroxide In 1,4-dioxane; water at 90℃; for 12h; Suzuki coupling; Inert atmosphere; | 97% |
9,10-Dibromoanthracene
1,1-dimethylethyl 2-ethenyl-1H-pyrrole-1-carboxylate
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; acetylacetone In N,N-dimethyl-formamide at 130℃; for 6h; Heck Reaction; Inert atmosphere; Sealed tube; | 97% |
Conditions | Yield |
---|---|
With propylamine; tetrakis(triphenylphosphine) palladium(0) at 60℃; for 48h; | 96% |
9,10-Dibromoanthracene
4-Vinylphenylboronic acid
9,10-(p,p'-divinyl)-diphenylanthracene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 85℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 96% |
With potassium carbonate; Pd2(dba)3/Pd(PtBu3)2 In toluene at 110℃; for 48h; Suzuki coupling; | 91% |
With potassium carbonate In toluene at 110℃; for 48h; Inert atmosphere; | 90% |
9,10-Dibromoanthracene
2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2.5h; Inert atmosphere; Schlenk technique; | 96% |
9,10-Dibromoanthracene
ethyl acrylate
diethyl 3,3'-(9,10-anthracenediyl)bisacrylate
Conditions | Yield |
---|---|
With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate In N,N-dimethyl-formamide at 120℃; for 48h; Heck reaction; | 95% |
With palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylamine In N,N-dimethyl-formamide at 100℃; for 10h; Heck reaction; | 94% |
9,10-Dibromoanthracene
dodecahedrene
Conditions | Yield |
---|---|
In benzene at 20℃; for 1h; | 95% |
9,10-Dibromoanthracene
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
Conditions | Yield |
---|---|
With potassium hydroxide; bis(dicyclohexylamine)palladium acetate In ethanol at 40℃; for 24h; Suzuki cross-coupling; | 95% |
9,10-Dibromoanthracene
Chlorodiisopropylphosphane
9,10-bis(diisopropylphosphanyl)anthracene
Conditions | Yield |
---|---|
Stage #1: 9,10-Dibromoanthracene With n-butyllithium In diethyl ether; hexane at -15 - 20℃; for 1h; Stage #2: Chlorodiisopropylphosphane In diethyl ether; hexane at 20℃; for 4h; Further stages.; | 95% |
Stage #1: 9,10-Dibromoanthracene With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at -30℃; Inert atmosphere; Schlenk technique; Stage #2: Chlorodiisopropylphosphane In tetrahydrofuran; diethyl ether; hexane at 35 - 40℃; Inert atmosphere; Schlenk technique; | 20.6% |
9,10-Dibromoanthracene
9,10-dibromo-1,2,3,4-tetrabromo-1,2,3,4-tetrahydroanthracene
Conditions | Yield |
---|---|
With bromine In tetrachloromethane at 25℃; UV-irradiation; stereoselective reaction; | 95% |
With bromine In tetrachloromethane for 48h; Irradiation; | 71% |
With bromine In tetrachloromethane at 25℃; Irradiation; | |
With bromine In tetrachloromethane Irradiation; stereoselective reaction; |
4-Methoxystyrene
9,10-Dibromoanthracene
9,10-bis(4-methoxystyryl)anthracene
Conditions | Yield |
---|---|
With potassium phosphate; palladium diacetate In N,N-dimethyl acetamide at 110℃; for 24h; | 95% |
With potassium phosphate; palladium diacetate In N,N-dimethyl acetamide at 110℃; for 24h; |
Conditions | Yield |
---|---|
In toluene at 160℃; for 4h; | 95% |
IUPAC Name: 9,10-Dibromoanthracene
Synonyms of Anthracene, 9,10-dibromo- (CAS NO.523-27-3): 9,10-Dibromoanthracene ; EINECS 208-342-4 ; NSC 6263
CAS NO: 523-27-3
Molecular Formula: C14H8Br2
Molecular Weight: 336.0213
Molecular Structure:
Melting Point: 220-225 °C
ProductCategories: Aromatic Compounds ; Miscellaneous ; Electronic Chemicals ; Anthracenes ; Anthracene series ; Aryl ; C13 to C37+ ; Halogenated Hydrocarbons
Index of Refraction: 1.748
Molar Refractivity: 77.31 cm3
Molar Volume: 190 cm3
Surface Tension: 54.3 dyne/cm
Density of 1.768 g/cm3
Flash Point: 248.1 °C
Enthalpy of Vaporization: 65.56 kJ/mol
Boiling Point: 427.1 °C at 760 mmHg
Vapour Pressure: 4.19E-07 mmHg at 25°C
Anthracene, 9,10-dibromo- (CAS NO.523-27-3) is used as intermediates in organic synthesis.
Hazard Codes of Anthracene, 9,10-dibromo- (CAS NO.523-27-3): Xi,N
Risk Statements: 36/37/38-50/53
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.
Safety Statements: 37/39-26-61-60-36
S37/39: Wear suitable gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
S60: This material and its container must be disposed of as hazardous waste.
S36: Wear suitable protective clothing.
RIDADR UN 3077
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