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Sigma-Aldrich

9-Phenanthrylmagnesium bromide

0.5 M in THF

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About This Item

Empirical Formula (Hill Notation):
C14H9BrMg
CAS Number:
71112-64-6
Molecular Weight:
281.43
MDL number:
MFCD00672008
UNSPSC Code:
12352103
PubChem Substance ID:
24880126
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

bp

65 °C (lit.)

density

0.970 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

Br[Mg]c1cc2ccccc2c3ccccc13

InChI

1S/C14H9.BrH.Mg/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13;;/h1-9H;1H;/q;;+1/p-1

InChI key

ACMUZKQPXSHTGB-UHFFFAOYSA-M

General description

9-phenanthrylmagnesium bromide is a Grignard reagent. It can be prepared using magnesium turnings and 9-bromophenanthrene under anhydrous condition.

Application

9-Phenanthrylmagnesium bromide can be used as a reagent to prepare:
  • 9-alkyl and 9-arylthiophenanthrenes by reacting with alkyl or aryl thiol compounds.
  • (S)-α-methylbenzyl 1-(9-phenanthryl)-2-naphthoate by treating with (S)- α -methylbenzyl methoxy-2-naphthoate.
  • 1-(9-Phenanthryl)-1-phenylethanol (carbinol) by reacting with acetophenone. The obtained carbinol undergoes dehydration reaction in the presence of acetic acid and sulfuric acid to afford 1-(9-phenanthryl)-1-phenylethene (PPE).

Legal Information

Product of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

target_organs

Respiratory system

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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The use of the DPE radical polymerization method for the synthesis of chromophore-labelled polymers and block copolymers
Kos T, et al.
European Polymer Journal, 41(6), 1265-1271 (2005)
Novel acyclic nitroxides for nitroxide-mediated polymerization: Kinetic, electron paramagnetic resonance spectroscopic, X-ray diffraction, and molecular modeling investigations
Lagrille O, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 44(6), 1926-1940 (2006)
Synthesis of 9-alkyl-and 9-arylthiophenanthrenes
Sipila K and Hase T
Synthetic Communications, 27(8), 1391-1393 (1997)
Absolute stereochemistry of 1-(9-phenanthryl)-2-naphthoic acid as determined by CD and X-ray methods
Harada N, et al.
Tetrahedron Asymmetry, 4(8), 1789-1792 (1993)

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