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B75409

Sigma-Aldrich

9-Bromophenanthrene

96%

Synonym(s):

9-Phenanthryl bromide

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About This Item

Empirical Formula (Hill Notation):
C14H9Br
CAS Number:
Molecular Weight:
257.13
Beilstein:
1869927
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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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N-heterocyclic-carbene complexes readily prepared from di-$\mu$-hydroxopalladacycles catalyze the Suzuki arylation of 9-bromophenanthrene
Serrano, et al.
Organometallics, 34, 522-533 (2005)
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)
Tanimoto
Bulletin of the Institute of Maritime and Tropical Medicine in Gdynia, 58, 289-292 (1980)
Aryne cycloaddition reactions in the synthesis of large polycyclic aromatic compounds
Perez, et al,
European Journal of Organic Chemistry, 2013, 5981-6013 (2013)
Charge-transfer complexes of brominated polycyclic aromatic hydrocarbons
Spotswood, T Mcl
Australian Journal of Chemistry, 15, 278-289 (1962)
Long Zhao et al.
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

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