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Merck
CN

B75409

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
209-351-6
Beilstein/REAXYS Number:
1869927
MDL number:
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Product Name

9-Bromophenanthrene, 96%

InChI key

RSQXKVWKJVUZDG-UHFFFAOYSA-N

InChI

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

SMILES string

Brc1cc2ccccc2c3ccccc13

assay

96%

form

powder

bp

180-190 °C/2 mmHg (lit.)

mp

60-64 °C (lit.)

Quality Level

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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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Aryne cycloaddition reactions in the synthesis of large polycyclic aromatic compounds
Perez, et al,
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)
Tanimoto
Bulletin of the Institute of Maritime and Tropical Medicine in Gdynia, 58, 289-292 (1980)
Charge-transfer complexes of brominated polycyclic aromatic hydrocarbons
Spotswood, T Mcl
Australian Journal of Chemistry, 15, 278-289 (1962)
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)
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)

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