9,10-Dibromoanthracene

Catalog Number	ACM523273
CAS Number	523-27-3
Synonyms	Anthracene,9,10-dibromo-
IUPAC Name	9,10-dibromoanthracene
Molecular Weight	336.02
Molecular Formula	C14H8Br2
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
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.