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:
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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Long Zhao et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 20(6), 791-797 (2019-02-03)
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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)
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)
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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