2-Bromofluorene Property

Melting point:

112-114 °C (lit.)

Boiling point:

185 °C/135 mmHg (lit.)

Density 

1.4187 (rough estimate)

refractive index 

1.6290 (estimate)

Flash point:

185°C/135mm

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in chloroform and ethyl acetate.

form 

Slightly Crystalline Powder or Flakes

color 

White to slightly yellow

BRN 

1946701

InChIKey

FXSCJZNMWILAJO-UHFFFAOYSA-N

CAS DataBase Reference

1133-80-8(CAS DataBase Reference)

NIST Chemistry Reference

9H-Fluorene, 2-bromo-(1133-80-8)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29039990

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.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

2-Bromofluorene Chemical Properties,Usage,Production

description

2-Bromofluorene is an isolated product of coal tar and its derivatives are used as important raw materials for fine chemicals. It is often used as synthetic intermediate of the OLED material in industry, by the reaction of barbier-type ultrasonic radiation, It is also used to study the conversion of aryl bromides to aryl triethoxy silane.
Lab Preparation Methods: propylene carbonate is used as solvent, N-bromosuccinimide (NBS) is used as brominated reagent to carry bromination reaction of fluorine, and this reaction can synthesize 2-bromofluorene and 2,7-dibromofluorene. By the investigation of reaction temperature, NBS amount, the adding methods, the optimal reaction conditions for the synthesis of 2-bromofluorene is confirmed. The optimal reaction conditions are: reaction temperature is 23℃, the molar ratio of NBS with fluorine is 1.1:1, NBS is added by stage addition. First fluorene and propylene carbonate is preheated to 60℃, so fluorine is all dissolved, and then it drops to the reaction temperature, NBS is added by stage addition. 2-bromofluorene and 2,7-dibromofluorene recrystallizes with ethanol and acetic acid respectively, the purity of target product of liquid chromatography can reach more than 99%.

Uses

(1) It can be used as pharmaceutical intermediate, it is also important intermediate in the synthesis of optoelectronic material.
(2) By ultrasonic radiation of Barbier-type reaction, 2-bromofluorene is used for the study of aryl bromide (aryl bromides) converts to aryl triethoxysilane (aryltriethoxysilanes). It is also for the preparation of N-carbazole fluorene oligomers end-capped. It can be used as intermediates of OLED materials in industry.

Chemical Properties

white to slightly yellow crystalline powder

Uses

2-Bromofluorene was used in the synthesis of end-capping reagent 2-bromo-9,9-di-nhexylfluorene. It has been used in the preparation of poly(di-n-hexylfluorene)s end capped with 2-bromofluorene, 2-bromo-9,9-di-n-hexylfluorene and 9-bromoanthracene through Ni(0) mediated polymerization. It was also used in the synthesis of 2-bromo-9,9-dihexylfluorene.

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 4327, 1958 DOI: 10.1021/ja01549a053

General Description

2-Bromofluorene is a nonintrusive end-capping reagent to control molecular weights and to generate well-defined oligomers. It is used as a reagent for the preparation of dibromofluorene-labelled polystyrene by nitroxide-mediated polymerization. It is also being used in the agricultural sector as a fungicide for tomato disease control. Its carcinogenic effects on humans are currently being investigated.