9-Bromophenanthrene

9-Bromophenanthrene Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

9-Bromophenanthrene Chemical Properties,Usage,Production

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