563749
9-Phenanthrylmagnesium bromide
0.5 M in THF
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About This Item
Fórmula empírica (notación de Hill):
C14H9BrMg
Número de CAS:
Peso molecular:
281.43
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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reaction suitability
reaction type: Grignard Reaction
Quality Level
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.
Rieke is a registered trademark of Rieke Metals, Inc.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
target_organs
Respiratory system
supp_hazards
Storage Class
3 - Flammable liquids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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)
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)
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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