9,10-Dibromoanthracene

Base Information

• Chemical Name: 9,10-Dibromoanthracene
• CAS No.: 523-27-3
• Molecular Formula: C14H8Br2
• Molecular Weight: 336.026
• Hs Code.: 29039990
• European Community (EC) Number: 208-342-4
• NSC Number: 6263
• UNII: 61CP7C5Y82
• DSSTox Substance ID: DTXSID5049312
• Nikkaji Number: J6.630C
• Wikipedia: 9,10-Dibromoanthracene
• Wikidata: Q27263331
• ChEMBL ID: CHEMBL3183379
• Mol file: 523-27-3.mol

Synonyms:9,10-Dibromoanthracene;523-27-3;Anthracene, 9,10-dibromo-;9,10-Dibromo-anthracene;C14H8Br2;MFCD00001244;UNII-61CP7C5Y82;DTXSID5049312;61CP7C5Y82;NSC 6263;NSC-6263;EINECS 208-342-4;NSC6263;9,10 dibromoanthracene;Anthracene,10-dibromo-;9,10 -dibromoanthracene;9,10- dibromoanthracene;SCHEMBL28511;9,10-Dibromoanthracene, 98%;C14-H8-Br2;CHEMBL3183379;DTXCID0029268;AMY11187;BCP06867;Tox21_202923;BBL002460;STK286015;9,10-DIBROMOANTHRACENE [MI];AKOS003241118;AC-4953;CS-W011924;NCGC00260469-01;AS-14616;CAS-523-27-3;SY012827;D0166;FT-0621594;EN300-68262;W-105834;Q27263331

Chemical Property of 9,10-Dibromoanthracene

Chemical Property:

• Appearance/Colour: yellow to yellow-green fluffy powder
• Vapor Pressure: 4.19E-07mmHg at 25°C
• Melting Point: 220-225 °C
• Refractive Index: 1.748
• Boiling Point: 427.1 °C at 760 mmHg
• Flash Point: 248.1 °C
• PSA: 0.00000
• Density: 1.768 g/cm³
• LogP: 5.51800
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform
• Water Solubility.: Soluble in water.
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 335.89723
• Heavy Atom Count: 16
• Complexity: 203

Purity/Quality:

99.0%min ^*data from raw suppliers

9,10-Dibromoanthracene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53
• Safety Statements: 37/39-26-61-60-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Polyaromatics
• Canonical SMILES: C1=CC=C2C(=C1)C(=C3C=CC=CC3=C2Br)Br
• 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. 9,10-Dibromoanthracene is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Technology Process of 9,10-Dibromoanthracene

There total 48 articles about 9,10-Dibromoanthracene 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) → 9,10-Dibromoanthracene (523-27-3)

Guidance literature:

With N-Bromosuccinimide; lithium perchlorate; silica gel; In dichloromethane; at 20 ℃; for 0.0833333h;

DOI:10.1139/v05-001

Reference yield: 85.0%

9-Bromoanthracene (1564-64-3) → 9,10-Dibromoanthracene (523-27-3)

Guidance literature:

With N-Bromosuccinimide; C₅H₁₃NO₃S; In n-heptane; at 25 ℃; for 19h; Reagent/catalyst; Darkness;

DOI:10.1039/d0cc04673f

Reference yield: 84.0%

anthracene (120-12-7) → 9-Bromoanthracene (1564-64-3) + 9,10-Dibromoanthracene (523-27-3)

Guidance literature:

With N-Bromosuccinimide; 2,4,6-trimethylaniline; In dichloromethane; at 0 ℃; for 8h; regioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201502234

upstream raw materials:

9,10-dihydroanthracene

9,19-Dibromo-9,10-dihydroanthracene

diethyl ether

1,2,3,4,9,10-hexabromo-1,2,3,4-tetrahydro-anthracene

Downstream raw materials:

9,10-Ethano-9,10-dibrom-9,10-dihydro-anthracen-11,12-dicarbonsaeureanhydrid

9-Bromoanthracene

9,10-diformylanthracene

anthracene

Refernces

9,10-diarylanthracenes as molecular switches: Syntheses, properties, isomerisations and their reactions with singlet oxygen

10.1002/chem.200801355

The research focuses on the synthesis, properties, and isomerization behavior of 9,10-diarylanthracene compounds, which are polyaromatic hydrocarbons with potential applications in electronic and photonic devices. The study aims to explore the reversible addition of singlet oxygen to these compounds, making them suitable for use as photochromic materials and photoresists in lithography. The researchers synthesized a series of 9,10-diarylanthracenes with various substituents at the ortho positions using palladium-catalyzed cross-coupling reactions. They found that these compounds can exist as stable syn and anti isomers, which exhibit different physical properties and reactivity towards singlet oxygen. The reactions with singlet oxygen revealed different reactivities and reaction pathways depending on the size and electronic nature of the substituents. The study concluded that 9,10-diarylanthracenes are ideal substrates for molecular switches that operate under mild and environmentally friendly conditions. Key chemicals used in the process include 9,10-dibromoanthracene, various arylboronic acids, tetrakis(triphenylphosphine)palladium, and potassium carbonate.

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