Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

563749

Sigma-Aldrich

9-Phenanthrylmagnesium bromide

0.5 M in THF

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Quality Level

100

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBQ2567
SHBL4206
SHBH9994
61596BP
05196DM

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service