2-Bromofluorene
2-Bromofluorene
CAS: 1133-80-8
Molecular Formula: C13H9Br
2-Bromofluorene - Names and Identifiers
| Name | 2-Bromofluorene |
| Synonyms | BROMOFLUORENE 2-Bromofluorene 3-bromo-9H-fluorene 2-broMo-2H-fluorene 2-bromo-9H-fluorene 2-Bromofluorene, Pract. 2-broMo-9H-fluorene(2BF) 2-BroMofluorene, BroMofluorene 4-Bromo-2,2'-methylenebiphenyl |
| CAS | 1133-80-8 |
| EINECS | 214-480-6 |
| InChI | InChI=1/C13H9Br/c14-11-6-5-10-7-9-3-1-2-4-12(9)13(10)8-11/h1-6,8H,7H2 |
| InChIKey | FXSCJZNMWILAJO-UHFFFAOYSA-N |
2-Bromofluorene - Physico-chemical Properties
| Molecular Formula | C13H9Br |
| Molar Mass | 245.11 |
| Density | 1.4187 (rough estimate) |
| Melting Point | 112-114 °C (lit.) |
| Boling Point | 185 °C/135 mmHg (lit.) |
| Flash Point | 185°C/135mm |
| Solubility | Soluble in chloroform and ethyl acetate. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White to yellow crystalline powder |
| Color | White to slightly yellow |
| BRN | 1946701 |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.6290 (estimate) |
| MDL | MFCD00001115 |
| Use | 2-bromofluorene was used to study the conversion of aryl bromide (aryl bromides) to aryltriethoxysilane (aryltriethoxysilanes) by Barbier-type reactions irradiated with ultrasound. It is also used to prepare N-carbazole end-capped oligofluorene. Used as an intermediate in OLED materials in industry. |
2-Bromofluorene - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| HS Code | 29039990 |
| Hazard Class | IRRITANT |
2-Bromofluorene - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| use | fluorene is one of the separation products of coal tar, with a wide range of uses and low price. as an important raw material of fine chemicals, its derivatives can be used in the fields of medicine, pesticides, dyes, plastics and functional polymer materials. 2-Bromofluorene is one of fluorene derivatives, which can be used in the synthesis of medicine and OLED materials, especially the 9-position modification of 2-bromofluorene, and can be used to synthesize various materials with unique photoelectric properties. 2-bromofluorene is used as a reagent to prepare dibromofluorobutadiene-labeled polystyrene through nitrogen oxide-mediated polymerization. In the agricultural sector, it is also used as a fungicide for tomato disease control. Its carcinogenic effects on humans are currently being studied. 2-bromofluorene is used as a reagent for the preparation of dibrofluorene-labeled polystyrene through nitro-oxygen-mediated polymerization. It is also used in agriculture as a fungicide for the control of tomato diseases. Its carcinogenic effects on humans are currently being studied. Pharmaceutical intermediates are also important intermediates for the synthesis of photoelectric materials Through the Barbier-type reaction of ultrasonic radiation, 2-bromofluorene is used to study the conversion of aryl bromides into aryl triethoxysilane (aryltriethoxysilanes). It is also used to prepare N-carbazole end-trapped oligofluorene. Used as an intermediate in OLED materials in industry. |
| preparation | add 172g of hydrobromic acid (0.98mol) and 32.3 g2-aminofluorene (0.178mol) with a mass fraction of 46% into a 500mL three-mouth bottle, stir, heat and reflux for 2 hours. Heat in a water bath at 50 ℃, add 25.5g of cuprous bromide (0.178mol), after stirring evenly, dropwise add 14.8g of sodium nitrite (0.214mol) and 70mL of water to prepare a solution, continue to heat preservation reaction for 1 hour after dropping, add 200mL of toluene and 50mL of water, stir for 30 minutes to dissolve the product, filter and desalinate, separate liquid, wash with water, concentrate, add 175mL of ethanol to recrystallize to obtain 38.7g of light yellow crystal product with a yield of 88.7%, the purity of gas chromatography is 99.4%. Heat and dissolve the product with 230mL of petroleum ether (90-120 ℃), pass through a preheated chromatography column filled with 40g of silica gel (80-120 mesh) under normal pressure, and rinse the column with 40mL of hot petroleum ether each time after passing through, and rinse the column three times in total. The column solution is cooled, frozen and crystallized, and filtered to obtain 34.6g of white flake crystal with 79.3% yield, 99.85% gas chromatography purity and 99.69%(254nm) liquid chromatography purity, the melting point is 113.3-113.5 ℃(0.5 ℃/min), and the product is 2-bromofluorene with high purity. |
| Overview | Industrial 2-bromofluorene is often used as an intermediate in the synthesis of OLED materials. Through the barbier-type reaction with ultrasonic radiation, 2-bromofluorene can also be used to study the conversion of aryl bromide to aryl triethoxysilane. laboratory preparation method: 2-bromofluorene and 2,7-dibromofluorene were synthesized by bromination reaction of fluorene with propylene carbonate as solvent and N-bromosuccinimide (NBS) as bromination reagent. The best reaction conditions for the synthesis of 2-bromofluorene were determined by investigating the reaction temperature, the amount of NBS and the addition method. The optimum reaction conditions were as follows: the reaction temperature was 23 ℃, the molar ratio of NBS to fluorene was 1.1: 1, and NBS was added in batches. First preheat fluorene and propylene carbonate to 60°C to dissolve all fluorene, then reduce to the reaction temperature, and add NBS in batches. 2-bromofluorene and 2, 7-dibromofluorene were recrystallized with absolute ethanol and glacial acetic acid respectively, and the liquid chromatographic purity of the target product could reach above 99%. |
Last Update：2024-04-09 19:05:09
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