9,10-Dibromoanthracene
Catalog Number
ACM523273
CAS
523-27-3
IUPAC Name
9,10-dibromoanthracene
Synonyms
Anthracene,9,10-dibromo-
Application
The purpose of 9,10-Dibromoanthracene is multifaceted, as it serves primarily as a dibrominated polycyclic aromatic hydrocarbon (PAH) used in various chemical and photochemical reactions. As a low-molecular-weight organic semiconductor, it has the unique ability to act as an energy acceptor and activator in processes that produce chemiluminescence. This compound, characterized by two bromine atoms substituted on the central ring of anthracene, offers extended conjugation through functional groups, enabling reactions such as Stille and Suzuki couplings. Additionally, 9,10-Dibromoanthracene has the notable distinction of being the first single molecule with a chemical reaction observed using advanced microscopy techniques. Its role extends to serving as an initiator in visible-spectrum solar-light-mediated benzylic C-H oxygenation, activated by solar light or blue LED, making it an invaluable component in modern organic synthesis and photochemical applications.
Molecular Weight
336.02
Molecular Formula
C14H8Br2
Product Information
Canonical SMILES
C1=CC=C2C(=C1)C(=C3C=CC=CC3=C2Br)Br
InChI
InChI=1S/C14H8Br2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H
InChI Key
BRUOAURMAFDGLP-UHFFFAOYSA-N
Melting Point
227 °C
Purity
99.5%+
Density
1.7167 (estimate)
Appearance
Yellow to Orange to Green powder to crystal
Complexity
203
Exact Mass
335.89723g/mol
Hazard Statements
H315-H319-H335
Heavy Atom Count
16
MDL Number
MFCD00001244
Monoisotopic Mass
333.89928g/mol
Precautionary Statements
P261-P280-P302+P352-P305+P351+P338
Reaxys Registry Number
1912109
Rotatable Bond Count
0
Signal Word
Warning
Solubility In Water
Insoluble
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