ChemicalBook > CAS DataBase List > 9-Bromoanthracene

9-Bromoanthracene

Product Name
9-Bromoanthracene
CAS No.
1564-64-3
Chemical Name
9-Bromoanthracene
Synonyms
9-BROMOANTHRENE;9-BROMOANTHRACENE;9-Anthryl bromide;MS-BROMOANTHRACENE;10-Bromoanthracene;9-Bromo anthrecene;TIMTEC-BB SBB007978;RARECHEM AQ BD AN02;9-Anthracyl bromide;Anthracene, 9-bromo-
CBNumber
CB5319891
Molecular Formula
C14H9Br
Formula Weight
257.13
MOL File
1564-64-3.mol
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9-Bromoanthracene Property

Melting point:
97-100 °C (lit.)
Boiling point:
303.85°C (rough estimate)
Density 
1.4251 (rough estimate)
refractive index 
1.6404 (estimate)
storage temp. 
Sealed in dry,Room Temperature
solubility 
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form 
Powder
color 
Yellow
Water Solubility 
Insoluble in water.
BRN 
1869747
InChI
InChI=1S/C14H9Br/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9H
InChIKey
ZIRVQSRSPDUEOJ-UHFFFAOYSA-N
SMILES
C1=C2C(C=C3C(=C2Br)C=CC=C3)=CC=C1
CAS DataBase Reference
1564-64-3(CAS DataBase Reference)
NIST Chemistry Reference
9-Bromoanthracene(1564-64-3)
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Safety

Hazard Codes 
Xi
Safety Statements 
22-24/25
WGK Germany 
3
Hazard Note 
Irritant
HS Code 
29049090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H341Suspected of causing genetic defects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
B56609
Product name
9-Bromoanthracene
Purity
94%
Packaging
5g
Price
$79.5
Updated
2024/03/01
Sigma-Aldrich
Product number
B56609
Product name
9-Bromoanthracene
Purity
94%
Packaging
25g
Price
$345
Updated
2024/03/01
TCI Chemical
Product number
B0872
Product name
9-Bromoanthracene
Purity
>95.0%(GC)
Packaging
5g
Price
$23
Updated
2024/03/01
TCI Chemical
Product number
B0872
Product name
9-Bromoanthracene
Purity
>95.0%(GC)
Packaging
25g
Price
$76
Updated
2024/03/01
Alfa Aesar
Product number
L06733
Product name
9-Bromoanthracene, 96%
Packaging
5g
Price
$57.65
Updated
2024/03/01
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9-Bromoanthracene Chemical Properties,Usage,Production

Description

9-bromoanthracene is a kind of bromine-derived anthracene. It is known to be able to reversibly photodimerize in a head-to tail fashion upon irradiation by long-wavelength ultraviolet light. The photodimers of 9-bromoanthracene are suitable to be used as alkyl halide initiators in the atom transfer radical polymerization (ATRP) reactions. It is also used as the intermediate for the preparation of the 9-substitued form of the polycyclic aromatic hydrocarbon (PAH) anthracene.

Chemical Properties

white to light yellow crystal powder. boiling point 190°C (0.16kPa, sublimation), relative density 1.409. soluble in acetic acid; carbon disulfide.

Uses

9-Bromoanthracene acts as an intermediate in the preparation of 9-substituted derivative of the polycyclic aromatic hydrocarbon (PAH) anthracene.

Preparation

Anthracene (5 g, 28.05 mmol) was dissolved in CHCl3. Then N-bromosuccinimide (NBS，4.99 g, 28.05 mmol) was added in batches away from light, and the reaction solution was continuously stirred for 12 h. The resulting mixture was stirred for another 30 min with appropriate water, and extracted with CH2Cl2. The CH2Cl2 solution was dried over anhydrous MgSO4. After removing CH2Cl2 solvent, the residue was recrystallized from anhydrous ethanol to give 4.78 g (66.3 %) of a green-yellow needle solid 9-Bromoanthracene. 1H NMR (500 MHz, CDCl3) δ 8.55 (d, J = 8.9 Hz, 2H), 8.48 (s, 1H), 8.03 (d, J = 8.4 Hz, 2H), 7.67 – 7.60 (m, 2H), 7.56 – 7.51 (m, 2H). EI-MS (m/z): Calculated for C14H9Br: 257.13. Found [M+ ]: 255.96.
Synthesis of 9-bromoanthracene

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 2740, 1992 DOI: 10.1021/jo00035a038

Purification Methods

Crystallise 9-bromoanthracene from MeOH or EtOH followed by sublimation in vacuo. [Masnori et al. J Am Chem Soc 108 126 1986, Beilstein 5 IV 2295.]

Properties and Applications

9-Bromoanthracene could be used to synthesise 6-bromoaceanthrylene-1,2-dione by Friedel-Crafts acylation reaction with oxalyl chloride. The pure 9-Bromoanthracene’s energy level is -5.710 eV. A 1:1 co-crystal of Picric acid and 9-Bromoanthracene was prepared by a solvent evaporation method. The PIC: BRA co-crystal shows significantly reduced impact sensitivity relative to pure Picric acid. The primary non-covalent interaction occurs between the electron-poor π-system of Picric acid and the electron-rich π-system of 9-Bromoanthracene. The distance between the Picric acid centroid and the 9-Bromoanthracene centroid was measured to be 3.492 Å, a typical value in materials which exhibit aromatic face-to-face πinteractions (<4.00 Å). An interaction is also indicated between aromatic hydrogen on the 9-Bromoanthracene ring and nitro group oxygen on a parallel Picric acid ring (C3-H3…O6). The donor-acceptor π ... π interactions dominate the formation of the Picric Acid co-crystal. The π electron cloud of the 9-Bromoanthracene ring is concentrated towards the electron-poor region at the centre of the Picric acid moiety, and the two rings combine. The π system of picric acid is known to deform due to the electron-withdrawing effect of nitro groups and an electron vacancy formed at the centre of the ring. This is partially filled by π electrons of the 9-Bromoanthracene ring. In other words, a charge transformation complex is formed[4].

References

[1]Cohen, Nicole A., et al. Macromolecular Chemistry and Physics 210.3 ‐4 (2009): 263-268.
[2]Xu, Xiaoming, Wenzhe Lu, and Richard B. Cole. Analytical chemistry 68.23 (1996): 4244-4253.
[3]Dang, Hung, and Miguel A. Garcia-Garibay. Journal of the American Chemical Society 123.2 (2001): 355-356.
[4] Se Hun Kim. “Highly efficient deep-blue emitting organic light emitting diode based on the multifunctional fluorescent molecule comprising covalently bonded carbazole and anthracene moieties.” Journal of Materials Chemistry B 13 1 (2011): 9139–9148.

9-Bromoanthracene Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 9-Bromoanthracene manufacturers

Shanghai Qyubiotech Co., Ltd.
Product
9-Bromoanthracene 1564-64-3
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%+
Supply Ability
10000kgs per Month
Release date
2022-10-11
Shanghai Daken Advanced Materials Co.,Ltd
Product
Anthracene, 9-bromo- 1564-64-3
Price
US $0.00/KG
Min. Order
1KG
Purity
98.00%
Supply Ability
150KG /month
Release date
2021-11-19
Henan Fengda Chemical Co., Ltd
Product
9-Bromoanthracene 1564-64-3
Price
US $100.00-1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2023-12-26

1564-64-3, 9-BromoanthraceneRelated Search:

9-(bromomethyl)anthracene ANTHRACENE, 9-BROMO-10-(1-NAPHTHALENYL)- 9-Bromo-10-(2-naphthyl)anthracene 10,10'-Dibromo-9,9'-bianthryl 9-Bromoanthracene 9,10-Dibromoanthracene 10-BROMOANTHRACENE-9-BORONIC ACID 7-BROMOBENZ[A]ANTHRACENE 2-BROMOANTHRACENE 1,5-DIBROMOANTHRAQUINONE 2,6-Dibromoanthraquinone 2-Bromoanthraquinone 1-amino-2-bromo-4-(phenylamino)anthraquinone Bromaminic acid 1-Methylamino-4-bromo anthraquinone 1-bromoanthracene-9,10-dione 2,6-DIBROMOANTHRACENE 1-amino-4-bromoanthracene-9,10-dione

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  • 9-Anthracyl bromide
  • 50KG/100KG(CIF INDIA COURIER/AIR)
  • RARECHEM AQ BD AN02
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  • TIMTEC-BB SBB007978
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  • 9-Bromoanthracene,96%
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  • 9-Bromoanthracene, 95%, for synthesis
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  • 9-Bromoanthracene in isooctane
  • 1564-64-3
  • 15464-64-3
  • 1564-6-64-3
  • C14H9Br
  • C14H8Br
  • ARYL HALIDE
  • Halogenated Hydrocarbons
  • Organic Building Blocks
  • Aryl
  • C13 to C37+
  • Building Blocks
  • Anthracenes
  • blocks
  • Bromides
  • OLED materrials
  • Aryl
  • C13 to C37+
  • Halogenated Hydrocarbons
  • Aromatic Halides (substituted)
  • Anthracenes
  • Anthracene series
  • Aromatic Compounds
  • bc0001