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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:
573-17-1
Molecular Weight:
257.13
Beilstein:
1869927
EC Number:
209-351-6
MDL number:
MFCD00001174
UNSPSC Code:
12352100
PubChem Substance ID:
24892005
NACRES:
NA.22

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

B75409-10G:
B75409-BULK:
B75409-100G:
B75409-VAR:
B75409-25G:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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