9-Bromophenanthrene
- CAS NO.:573-17-1
- Empirical Formula: C14H9Br
- Molecular Weight: 257.13
- MDL number: MFCD00001174
- EINECS: 209-351-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2025-01-27 09:38:02
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What is 9-Bromophenanthrene?
Description
9-Bromophenanthrene is a luminescent material that fluoresces at short wavelengths and can be used as a molecular probe to detect the presence of other compounds and the mechanism of reaction, among other things.
Chemical properties
light yellow powder. soluble in toluene, and chloroform (50 mg/ml).
The Uses of 9-Bromophenanthrene
9-Bromophenanthrene is used as halogenated building block. Isotope labelled 9-Bromophenanthrene (B687200), a halogenated polycyclic aromatic hydrocarbon that has been seen to have a room temperature phosphorescence that can be induced by β-cyclodextrin (β-CD) in the presence of cyclohexane; however, trace Fe(III) causes a decrease of the RTP emission.
Preparation
9-Bromophenanthrene (90-94%) is produced by adding bromine to a refluxing solution of phenanthrene in carbon tetrachloride. This is the starting-point of 9-substituted phenanthrenes, e.g, when heated with cuprous cyanide at 260℃, 9-bromophenanthrene forms the corresponding cyano-compound; this may be hydrolysed to phenanthrene-9-carboxylic acid. Phenanthrene undergoes the Friedel-Crafts reaction mainly in the 3-, and to a small extent, in the 2-position. It is chloromethylated in the 9-position. When nitrated, phenanthrene gives a mixture of three mononitro-derivatives, the 3-isomer predominating. Sulphonation of phenanthrene gives a mixture of 1-, 2-, 3- and 9-phenanthrenesulphonic acids, and the ratio of these isomers depends on the temperature.
Properties of 9-Bromophenanthrene
Melting point: | 60-64 °C (lit.) |
Boiling point: | 180-190 °C/2 mmHg (lit.) |
Density | 1.4251 (rough estimate) |
refractive index | 1.6404 (estimate) |
Flash point: | >230 °F |
storage temp. | Sealed in dry,Room Temperature |
solubility | chloroform: 50 mg/mL, clear |
form | Powder |
color | Light yellow |
BRN | 1869927 |
InChI | InChI=1S/C14H9Br/c15-14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9H |
CAS DataBase Reference | 573-17-1(CAS DataBase Reference) |
NIST Chemistry Reference | Phenanthrene, 9-bromo-(573-17-1) |
Safety information for 9-Bromophenanthrene
Signal word | Warning |
Pictogram(s) |
![]() Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 9-Bromophenanthrene
InChIKey | RSQXKVWKJVUZDG-UHFFFAOYSA-N |
SMILES | C1=C2C(C3C(C(Br)=C2)=CC=CC=3)=CC=C1 |
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