ChemicalBook > CAS DataBase List > 9,10-Dibromoanthracene

9,10-Dibromoanthracene

Product Name
9,10-Dibromoanthracene
CAS No.
523-27-3
Chemical Name
9,10-Dibromoanthracene
Synonyms
9,10-Dibromoanthracene99%;NSC 6263;9,10-anthracene;ms-Dibromoanthracene;9, 10-Dibromoanthrac;9,I O-Dibromanthracen;9,1-Dibromoanthracene;9,1O-dibromoanthracene;9,10-DIRBOMOANTHRACENE;9,10-DIBROMOANTHRACENE
CBNumber
CB6318033
Molecular Formula
C14H8Br2
Formula Weight
336.02
MOL File
523-27-3.mol
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9,10-Dibromoanthracene Property

Melting point:
223-224 °C (lit.)
Boiling point:
342.21°C (rough estimate)
Density 
1.7167 (estimate)
refractive index 
1.6300 (estimate)
storage temp. 
Sealed in dry,Room Temperature
solubility 
Chloroform
form 
Fluffy Powder
color 
Yellow to yellow-green
Water Solubility 
Soluble in water.
Merck 
14,3018
BRN 
1912109
InChIKey
BRUOAURMAFDGLP-UHFFFAOYSA-N
CAS DataBase Reference
523-27-3(CAS DataBase Reference)
NIST Chemistry Reference
Anthracene, 9,10-dibromo-(523-27-3)
EPA Substance Registry System
Anthracene, 9,10-dibromo- (523-27-3)
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Safety

Hazard Codes 
Xi,N
Risk Statements 
36/37/38-50/53
Safety Statements 
37/39-26-61-60-36
RIDADR 
UN 3077
WGK Germany 
3
TSCA 
Yes
HS Code 
29039990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D38855
Product name
9,10-Dibromoanthracene
Purity
98%
Packaging
10g
Price
$84.6
Updated
2024/03/01
Sigma-Aldrich
Product number
D38855
Product name
9,10-Dibromoanthracene
Purity
98%
Packaging
50g
Price
$149.4
Updated
2024/03/01
TCI Chemical
Product number
D0166
Product name
9,10-Dibromoanthracene
Purity
>98.0%(GC)
Packaging
25g
Price
$107
Updated
2024/03/01
TCI Chemical
Product number
D0166
Product name
9,10-Dibromoanthracene
Purity
>98.0%(GC)
Packaging
100g
Price
$236
Updated
2024/03/01
Alfa Aesar
Product number
L12680
Product name
9,10-Dibromoanthracene, 98%
Packaging
5g
Price
$32.65
Updated
2024/03/01
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9,10-Dibromoanthracene Chemical Properties,Usage,Production

Description

9,10-Dibromoanthracene is an organic chemical compound containing anthracene with two bromine atoms substituted on its central ring. As a symmetrically brominated anthracene derivative, it is bearing functional groups to extend its conjugation further mainly via C-C bond forming i.e. Stille and Suzuki coupling reactions. It is notable in that it was the first single molecule to have a chemical reaction observed by an atomic force microscope and scanning tunneling microscopy. It is a low-molecular-weight organic semiconductor. It can used as an initiator in visible-spectrum solar-light-mediated benzylic C–H oxygenation through solar light or the blue LED activate[1-2].

Chemical Properties

Yellow to yellow-green fluffy powder. Melting point 226°C. It can be sublimated and oxidized to generate anthraquinone. It is soluble in hot benzene and hot toluene, but only slightly soluble in alcohol, ether, and cold benzene. It is insoluble in water.

Uses

9,10-Dibromoanthracene is a dibrominated polycyclic aromatic hydrocarbon (PAH). 9,10-Dibromoanthracene is often used as an energy acceptor and activator in reactions that produce chemiluminescence.

Preparation

9,10-Dibromoanthracene is synthesized by the bromination of anthracene. The bromination reaction is carried out at room temperature using carbon tetrachloride as a solvent. Using 80-85% anthracene as raw material, adding bromine to react for half an hour, the yield is 83-88%.

Origin

9,10-Dibromoanthracene was first synthesized in 1923 by Ian (formerly Isidor) M. Heilbron and John S. Heaton, chemists working at the University of Liverpool.

Purification Methods

Recrystallise it from toluene, xylene or CCl4 (yellow needles), and sublime it in a vacuum [Johnston et al. J Am Chem Soc 109 1291 1987]. [Heilbron & Heaton Org Synth Coll Vol I 207 1941, Beilstein 5 H 665.]

References

[1] Santra S, et al. Visible-Spectrum Solar-Light-Mediated Benzylic C–H Oxygenation Using 9,10-Dibromoanthracene As an Initiator. The Journal of Organic Chemistry, 2020; 86: 1164–1171.
[2] Watanabe M. Formation of aligned needle-like crystals of 9,10-dibromoanthracene in small droplets. Journal of Applied Polymer Science, 2023; 140: e54515.

9,10-Dibromoanthracene Preparation Products And Raw materials

Raw materials

Carbon tetrachloride Anthracene

Preparation Products

9,10-ANTHRACENEDICARBOXALDEHYDE
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View Lastest Price from 9,10-Dibromoanthracene manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
9,10-Dibromoanthracene 523-27-3
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-04-07
Speranza Chemical Co., Ltd.
Product
9,10-Dibromoanthracene 523-27-3
Price
US $450.00/KG
Min. Order
1KG
Purity
98%+
Supply Ability
300MT/year
Release date
2019-11-15
Henan Fengda Chemical Co., Ltd
Product
9,10-Dibromoanthracene 523-27-3
Price
US $100.00-1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2023-12-23

523-27-3, 9,10-DibromoanthraceneRelated Search:

1,2-DIBROMOETHYLENE 1,3-Dibromo-5,5-dimethylhydantoin 1,3-Bis(bromomethyl)benzene 2,2-Bis(bromomethyl)propane-1,3-diol DBDCB 2,4-DIBROMOPENTANE meso-2,3-Dibromosuccinic acid 1,2-Dibromopropane 2-Bromo-9,9-dimethylfluorene 9-Bromoanthracene ANTHRACENE, 9-BROMO-10-(1-NAPHTHALENYL)- 9,10-DIHYDROANTHRACENE Anthracene 9,10-DIBROMO-2-METHYLANTHRACENE 9,10-DIBROMOANTHRACENE-2-SULFONIC ACID 9,10-Dibromoanthracene-2-sulfonyl Chloride 2-TERTBUTYL-9,10-DIBROMOANTHRACENE 9,10-Dibromoanthracene-2-sulfonic Acid, Sodium Salt

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  • 523-27-3
  • C14H8Br2
  • C6H4CBr2C6H4
  • C13 to C37+
  • Aryl
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  • Aryl
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  • Halogenated Hydrocarbons
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