9-Bromophenanthrene Chemical Properties

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

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 Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

SF7197000

F 

8

Hazard Note 

Irritant

HS Code 

29036990

MSDS

• Language:English Provider:9-Bromophenanthrene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

9-Bromophenanthrene Usage And Synthesis

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).

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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