B75409
9-Bromophenanthrene
96%
Synonym(s):
9-Phenanthryl bromide
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About This Item
Quality Level
Assay
96%
form
powder
bp
180-190 °C/2 mmHg (lit.)
mp
60-64 °C (lit.)
SMILES string
Brc1cc2ccccc2c3ccccc13
InChI
1S/C14H9Br/c15-14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9H
InChI key
RSQXKVWKJVUZDG-UHFFFAOYSA-N
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General description
9-bromophenanthrene is a versatile halogenated organic compound that can be used as a reagent in various reactions such as Friedel-Crafts reaction and the Diels-Alder reaction. It is also used as a precursor for the synthesis of 9-bromoanthracene, 9-bromophenanthroline, and 9-bromophenanthridine.
Application
9-bromophenanthrene can be used as a building block in the synthesis of N-heterocyclic-carbene complexes via Suzuki−Miyaura cross-coupling reaction with aryl boronic acids.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Aryne cycloaddition reactions in the synthesis of large polycyclic aromatic compounds
European Journal of Organic Chemistry, 2013, 5981-6013 (2013)
Diels-Alder Addition of N, N-Diethyl-1, 3-butadienylamine to Dehydroaromatic Intermediates Generated from Some Haloaromatics (Commemoration Issue Dedicated to Professor Tatsuo Yamamoto on the Occasion of his Retirement)
Bulletin of the Institute of Maritime and Tropical Medicine in Gdynia, 58, 289-292 (1980)
Charge-transfer complexes of brominated polycyclic aromatic hydrocarbons
Australian Journal of Chemistry, 15, 278-289 (1962)
Chemphyschem : a European journal of chemical physics and physical chemistry, 20(6), 791-797 (2019-02-03)
For the last decades, the hydrogen-abstraction-acetylene-addition (HACA) mechanism has been widely invoked to rationalize the high-temperature synthesis of PAHs as detected in carbonaceous meteorites (CM) and proposed to exist in the interstellar medium (ISM). By unravelling the chemistry of the
N-heterocyclic-carbene complexes readily prepared from di-$\mu$-hydroxopalladacycles catalyze the Suzuki arylation of 9-bromophenanthrene
Organometallics, 34, 522-533 (2005)
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