| Identification | More | [Name]
9-Bromophenanthrene | [CAS]
573-17-1 | [Synonyms]
9-BROMOPHENANTHRENE
9-bromo-phenanthren
9-Phenanthryl bromide
9-Phenathryl bromide
9-phenathrylbromide
9-Bromophenanthrene,97%
9-Bromophenathrene
9-Bromophenanthrene,95%
Phenanthrene, 9-bromo-
9-Bromoanth raceme 96% | [EINECS(EC#)]
209-351-6 | [Molecular Formula]
C14H9Br | [MDL Number]
MFCD00001174 | [Molecular Weight]
257.13 | [MOL File]
573-17-1.mol |
| Chemical Properties | Back Directory | [Appearance]
light yellow powder | [Melting point ]
60-64 °C (lit.) | [Boiling point ]
180-190 °C/2 mmHg (lit.) | [density ]
1.4251 (rough estimate) | [refractive index ]
1.6404 (estimate) | [Fp ]
>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 | [InChIKey]
RSQXKVWKJVUZDG-UHFFFAOYSA-N | [SMILES]
C1=C2C(C3C(C(Br)=C2)=CC=CC=3)=CC=C1 | [CAS DataBase Reference]
573-17-1(CAS DataBase Reference) | [NIST Chemistry Reference]
Phenanthrene, 9-bromo-(573-17-1) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
SF7197000
| [F ]
8 | [Hazard Note ]
Irritant | [HS Code ]
29036990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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 | [Uses]
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. | [Synthesis]
The general procedure for the synthesis of 9-bromophenanthrene from phenanthrene was as follows: a 50 mL round-bottomed flask was charged with a magnetic stirrer, followed by the addition of a solvent mixture of acetic acid and water (9:1, 10 mL, by volume). Phenanthrene (514 mg, 2 mmol) and potassium bromide (215 mg, 1.8 mmol) were added sequentially to the flask and allowed to dissolve completely under magnetic stirring. Zinc-aluminum bromate layered double hydroxide (ZnAl-BrO3-LDH, 1.2 g, containing 1.2 mmol BrO3?) was added slowly in batches over a period of half an hour, and the reaction temperature was maintained at 40 °C with continuous stirring for 4 hours. The progress of the reaction was monitored by thin-layer chromatography (TLC) during the reaction using ethyl acetate and petroleum ether (1:15, v/v) as the unfolding agent. Upon completion of the reaction, the reaction mixture was extracted with dichloromethane (3 × 10 mL), and the combined organic phases were washed with distilled water (3 × 10 mL). The organic phase was dried over anhydrous sodium sulfate and filtered, and purified by column chromatography (eluent ratio of petroleum ether to ethyl acetate 15:1, v/v) to obtain the final white crystalline product in 91% yield. | [References]
[1] Organic Letters, 2003, vol. 5, # 18, p. 3317 - 3319
[2] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 2093 - 2094
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2005, vol. 180, # 2, p. 533 - 536
[4] Patent: CN107151197, 2017, A. Location in patent: Paragraph 0018; 0019; 0021-0024; 0025-0028
[5] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 7, p. 1918 - 1921 |
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