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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)
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
Synthesis of 9, 9?-biphenanthryl-10, 10?-bis (oxazoline) s and their preliminary evaluations in the Friedel-Crafts alkylations of indoles with nitroalkenes
Lin S, et al.
Tetrahedron, 65, 1010-1016 (2009)
Charge-transfer complexes of brominated polycyclic aromatic hydrocarbons
Spotswood, T Mcl
Australian Journal of Chemistry, 15, 278-289 (1962)
Aryne cycloaddition reactions in the synthesis of large polycyclic aromatic compounds
Perez, et al,
European Journal of Organic Chemistry, 2013, 5981-6013 (2013)

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