9-Bromoanthracene

Base Information

• Chemical Name: 9-Bromoanthracene
• CAS No.: 1564-64-3
• Molecular Formula: C14H9Br
• Molecular Weight: 257.129
• Hs Code.: 29049090
• European Community (EC) Number: 216-359-3
• NSC Number: 803
• UNII: 4KA5657H57
• DSSTox Substance ID: DTXSID6049224
• Nikkaji Number: J206.801J
• Wikidata: Q27259865
• ChEMBL ID: CHEMBL3183594
• Mol file: 1564-64-3.mol

Synonyms:9-Bromoanthracene;1564-64-3;Anthracene, 9-bromo-;9-Anthracenyl bromide;9-bromo anthracene;9-bromo-anthracene;DTXSID6049224;UNII-4KA5657H57;NSC 803;NSC-803;EINECS 216-359-3;MFCD00001243;4KA5657H57;9-bromoanthracene-d9;9-bromanthracen;NSC803;9-Bromoanthracene, 94%;10-BROMOANTHRACENE;9-ANTHRACYL BROMIDE;BIDD:GT0390;SCHEMBL132836;CHEMBL3183594;DTXCID2029080;Tox21_202958;AKOS008967293;AC-4961;CS-W010171;NCGC00260504-01;AS-15095;SY011479;CAS-1564-64-3;AM20030057;B0872;B2871;FT-0621630;EN300-17978;A809751;AB-131/40897137;W-108012;Q27259865

Chemical Property of 9-Bromoanthracene

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 6.28E-06mmHg at 25°C
• Melting Point: 97-100 °C(lit.)
• Refractive Index: 1.733
• Boiling Point: 389.7 °C at 760 mmHg
• Flash Point: 190.3 °C
• PSA: 0.00000
• Density: 1.479 g/cm³
• LogP: 4.75550
• Storage Temp.: 0-6°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 255.98876
• Heavy Atom Count: 15
• Complexity: 203

Purity/Quality:

99.5% ^*data from raw suppliers

9-Bromoanthracene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C=C3C=CC=CC3=C2Br
• 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.
• Uses: 9-Bromoanthracene acts as an intermediate in the preparation of 9-substituted derivative of the polycyclic aromatic hydrocarbon (PAH) anthracene.

Technology Process of 9-Bromoanthracene

There total 28 articles about 9-Bromoanthracene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

anthracene (120-12-7) → 9-Bromoanthracene (1564-64-3)

Guidance literature:

With bis(trifluoroacetoxy)iodobencene; trimethylsilyl bromide; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.joc.9b02784

Reference yield: 99.0%

(10-bromoanthracen-9-yl)boronic acid (641144-16-3) → 9-Bromoanthracene (1564-64-3)

Guidance literature:

With [Pd(N-phenylbenzaldimine)(OAc)(PPh₃)]; In tetrahydrofuran; at 20 ℃; for 24h; chemoselective reaction; Schlenk technique;

DOI:10.1039/c4ra09678a

Reference yield: 94.0%

1-(anthracen-10-yl)-2-bromoethanone (24100-41-2) → 9-acetylanthracene (784-04-3) + 9-Bromoanthracene (1564-64-3)

Guidance literature:

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; acetic acid; for 0.7h; Irradiation; Inert atmosphere;

DOI:10.1055/s-0037-1610629

upstream raw materials:

N-Bromosuccinimide

anthracene

9,19-Dibromo-9,10-dihydroanthracene

2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one

Downstream raw materials:

9-bromo-9,10-dihydro-9,10-ethano-anthracene-11,12-dicarboxylic acid-anhydride

anthracen-9-carboxylic acid

anthracen-9(10H)-one

9,10-Dibromoanthracene

Refernces

• 1、 Mosnaim,D.,Nonhebel,D.C.. "". . p. 1591 - 1595. Retrieved 1969.
• 2、 Zong, Zhi-Min,Zhang, Wei-Hong,Jiang, Qun,Lu, Jin,Wei, Xian-Yong. "Photochemical reactions of hydroarenes with N-bromosuccinimide". . p. 769 - 771. Retrieved 2002.
• 3、 Beringer,F.M. et al.. "-". . p. 685 - 689. Retrieved 1969.
• 4、 He, Xinxin,Wang, Xinyan,Tse, Ying-Lung Steve,Ke, Zhihai,Yeung, Ying-Yeung. "Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis". . p. 12632 - 12642. Retrieved 2021/10/21.
• 5、 Arrieta, Ana,Cossío, Fernando P.,Granados, Albert,Shafir, Alexandr,Vallribera, Adelina. "Stepwise mechanism for the bromination of arenes by a hypervalent iodine reagent". . p. 2142 - 2150. Retrieved 2020/03/11.