CAS 1564-64-3 9-Bromoanthracene - Materials / Alfa Chemistry

NAVIGATION

9-Bromoanthracene

PRICE INQUIRY

Catalog Number

ACM1564643

CAS Number

1564-64-3

Product Name

9-Bromoanthracene

Structure

Category

Small Molecule Semiconductor Building Blocks; Electroluminescence Materials; Organic Light-Emitting Diode (OLED) Materials; Other Electronic Materials

IUPAC Name

9-bromoanthracene

Molecular Weight

257.12g/mol

Molecular Formula

C14H9Br

Canonical SMILES

C1=CC=C2C(=C1)C=C3C=CC=CC3=C2Br

InChI

InChI=1S/C14H9Br/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9H

InChI Key

ZIRVQSRSPDUEOJ-UHFFFAOYSA-N

Purity

98%

Application

9-Bromoanthracene is a versatile chemical compound primarily used as an intermediate in the synthesis of 9-substituted derivatives of anthracene, a polycyclic aromatic hydrocarbon (PAH). It appears as a white to light yellow crystal powder, with a boiling point of 190°C under controlled conditions and a relative density of 1.409. Its solubility in acetic acid and carbon disulfide makes it particularly useful in various chemical reactions. This compound exhibits unique properties, such as the ability to photodimerize reversibly upon exposure to long-wavelength ultraviolet light, making its photodimers effective as alkyl halide initiators in atom transfer radical polymerization (ATRP) reactions. 9-Bromoanthracene is also involved in the Sonogashira reaction with ethynyltrimethylsilane, leading to diverse products, like 9-(trimethylsilylethynyl)anthracene, through mechanistic pathways involving palladium catalysts. Additionally, it can be used in Friedel-Crafts acylation reactions to synthesize specific aromatic compounds, such as 6-bromoaceanthrylene-1,2-dione. One notable application is the formation of charge-transfer complexes, exemplified by its co-crystal with picric acid, which displays reduced impact sensitivity due to strong π-π interactions. This myriad of applications underscores the importance of 9-Bromoanthracene in organic synthesis and materials science.

Complexity

203

Covalently-Bonded Unit Count

EC Number

216-359-3

Exact Mass

255.98876g/mol

Formal Charge

Heavy Atom Count

Log P

5.37 (LogP)

Monoisotopic Mass