16433-88-8

Basic information

• Product Name: 2,7-Dibromofluorene
• Synonyms: 2,7-Dibromo-9H-fluorene;Fluorene, 2,7-dibromo-;2,7-DIBROMOFLUORENE;TIMTEC-BB SBB007691;Aluminum oxide, fused, #325 mesh, 99+%;Dibromofluorene;2,7-Dibromofluorene, 98+%;2,7-Dibromofluorene,99%
• CAS NO: 16433-88-8
• Molecular Formula: C₁₃H₈Br₂
• Molecular Weight: 324.01
• EINECS: 1592732-453-0
• Product Categories: Fluorene Derivatives;blocks;Bromides;Fluorenes, Flurenones;Fluorenes;Fluorenes & Fluorenones;Aryl;C13 to C37+;Halogenated Hydrocarbons;Fluorene Series;OLED materials,pharm chemical,electronic;Thiadiazoles ,Benzothiazoles
• Mol File: 16433-88-8.mol

Chemical Properties

• Melting Point: 164-166 °C(lit.)
• Boiling Point: 329.77°C (rough estimate)
• Flash Point: 230.9 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.7203 (estimate)
• Vapor Pressure: 2.5E-06mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly)
• BRN: 2049205
• CAS DataBase Reference: 2,7-Dibromofluorene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-Dibromofluorene(16433-88-8)
• EPA Substance Registry System: 2,7-Dibromofluorene(16433-88-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 16433-88-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Light Emitting Devices (OLEDs):
2,7-Dibromofluorene is used as a template for the N-carbazole capped oligofluorenes, which show potential as hole-transporting materials for OLEDs. This application takes advantage of its ability to enhance the performance of these devices by improving their efficiency and brightness.
Used in Synthesis of Conjugated Polymers:
In the field of polymer chemistry, 2,7-Dibromofluorene is utilized in the synthesis of conjugated polymer, poly[9,9′-bis(6′′-N,N,N-trimethylammonium)hexyl)fluorene-co-alt-4,7-(2,1,3-benzothiadiazole) dibromide] (PFBT). This polymer is used in label-free DNA microarrays, which are essential tools in molecular biology and genomics research.
Used in Preparation of Blue Photoluminescent Polyfluorene:
2,7-Dibromofluorene is also employed in the preparation of blue photoluminescent unsymmetrically substituted polyfluorene. This application leverages its properties to create materials with specific optical and electronic characteristics, which are valuable in various optoelectronic applications.
Used in Preparation of Dendrimers:
Furthermore, 2,7-Dibromofluorene is used in the preparation of 2,7-dibromofluorene monomers containing benzyl ether dendrons (generations 1, 2, and 3) in the 9,9′-position of the fluorene ring. These dendrimers have potential applications in various fields, including drug delivery, catalysis, and sensing, due to their unique structural and functional properties.

InChI:InChI=1/C13H8Br2/c14-10-1-3-12-8(6-10)5-9-7-11(15)2-4-13(9)12/h1-4,6-7H,5H2

Upstream product

• 86-73-7 9H-fluorene 
• 1600-27-7 mercury(II) diacetate 
• 5744-03-6 dodecahydrofluorene 
• 23346-78-3 2,7-dibromo-fluorene-9-carboxylic acid 
• 73838-62-7 2,7-dibromo-fluorene-9-carboxylic acid methyl ester 
• 15465-80-2 (2,7-dibromo-fluoren-9-yl)-glyoxylic acid ethyl ester 
• 27192-95-6 2,7,2',7',2'',7''-hexabromo-[9,9';9',9'']terfluorene 
• 24764-32-7 2,7-dibromofluorenylidenetriphenyl-phosphorane 
• 67-56-1 methanol 
• 18833-08-4 2,7-dibromo-9-diazo-9H-fluorene 
• 106112-41-8 2,7-dibromo-3,6-di-t-butylfluorene 
• 27192-91-2 2,2',7,7'-tetrabromo-9,9'-bifluorenylidene 
• 75-03-6 ethyl iodide 
• 67-66-3 chloroform 

Downstream Products

• 857789-65-2 (2,7-dibromo-fluoren-9-yl)-phenyl ketone 
• 858440-75-2 N'-(2,7-dibromo-fluoren-9-ylidene)-N,N-dimethyl-p-phenylenediamine 
• 86-73-7 9H-fluorene 
• 39168-58-6 9H,9'H-2,2'-bifluorene 
• 14348-75-5 2,7-dibromofluorene-9-one 
• 26279-24-3 2,7,9-tribromofluorene 
• 1785-07-5 2,7-dibromo-4-nitro-9H-fluorene 
• 65550-90-5 2,7-dibromo-9-(4-methylbenzylidene)-9H-fluorene 
• 23000-28-4 2,7-Dibromo-9-(1-phenylmethylene)-9H-fluorene 
• 70600-01-0 2,7-dibromo-9-(3-chloro-benzylidene)-fluorene 
• 68570-33-2 2,7-dibromo-9-cinnamylidene-fluorene 
• 794-95-6 1,2-bis(4-(dimethylamino)phenyl)diazene oxide 
• 65439-99-8 2,7-dibromo-9-(4-iodo-benzylidene)-fluorene 

Relevant articles and documents

Condensed polycyclic compounds and organic light emitting device comprising the same

Disclosed are a condensed-cyclic compound and an organic light emitting device including the same, which can have high efficiency, low driving voltage and long lifespan. The condensed-cyclic compound is represented by chemical formula 1 which is (R1)_(a1)-(L)_n-(R2)_(a2), wherein L is selected among substituted or unsubstituted C_3-C_10 cycloalkylene, substituted or unsubstituted C_1-C_10 heterocycloalkylene, substituted or unsubstituted C_3-C_10 cycloalkenylene, substituted or unsubstituted C_1-C_10 heterocycloalkenylene, substituted or unsubstituted C_6-C_60 arylene, substituted or unsubstituted C_1-C_60 heteroarylene, and substituted or unsubstituted non-aromatic condensed polycycle.COPYRIGHT KIPO 2015

Simple and efficient method for obtaining fluorene and spirobifluorene bromide derivatives

A mild, simple, and efficient synthetic procedure for the preparation of 2-monobromo-, 2,7-dibromo-, and 2,2′,7,7′-tetrabromo-substituted spirobifluorene derivatives and their key intermediates, 2-monobromo- and 2,7-dibromo-substituted fluorene compounds, has been developed. The oxidative bromination of fluorene and spirobifluorene was achieved using NaBr/H2O2 as the bromine source. High conversion of the starting materials was achieved together with good selectivities under optimized reaction conditions. Copyright Taylor & Francis Group, LLC.

Pinacol Formation and Reduction of Aromatic Carbonyls with Magnesium-Methanol at Ambient Temperature

A simple and inexpensive procedure for the pinacol formation of aromatic aldehydes and reduction of aromatic ketones to the corresponding alcohols with magnesium in dry methanol at ambient temperature is reported. The pinacol formation and reduction are proposed to be proceeding by SET from magnesium.

Increasing the selectivity of bromination of aromatic compounds using Br2/SiO2

Br2/SiO2 possessed considerable practical advantages over traditional reagents for the bromination of aromatic hydrocarbons, e.g., toluene, o-, m-, and p-xylene, anthracene and phenol. In the presence of SiO2, toluene reacted with bromine instantly. Compounds containing electron-donating substituents showed mainly bromination on the rings. The behavior of o-, m-, and p-xylene showed predominant substitution on the rings. The bromination of phenol to p-bromophenol showed good yield at 81%. Naphthalene was monobrominated to 1-bromonaphthalene with a yield of 84% in 2 has the potential to alter reaction selectivity. It may be able to switch a mechanism from radical to polar, or to influence the regioselectivity of the products formed. In the absence of SiO2, selectivity was lost and a mixture of products by substitution of bromine atom on the ring and on the side chain without any preferability was obtained. The nature of silica gel was important for the success of the reaction. Optimal results were obtained with silica gel dried at 250°C for 1 hr.

Investigation of the 2,7-Dihalofluorenylidenes: Search for Heavy Atom Effects in the Reactions of Triplet Carbenes

The properties of the 2,7-dihalofluorenylidenes (Cl, Br, I) were examined by laser and EPR spectroscopy and by conventional chemical analyses.Their reactions with alcohols and olefins were studied.No evidence was found for the operation of a heavy atom effect in their reaction with methyl alcohol.Analysis of the kinetic and product results indicates an energy gap between the triplet (ground state) and the singlet for the three dihalofluorenylidenes of 4.2 +/- 0.5 kcal/mol, ca. twice the value of fluorenylidene itself.

Selective Preparation of Fluorene Derivatives Using the t-Butyl Function as a Positional Protective Group

Several 4-substituted 2,7-di-t-butylfluorene derivatives (3) were prepared by electrophilic substitutions of 2,7-di-t-butylfluorene (1). 4-Substituted fluorene (4), such as 4-bromo- (4a), 4-methyl (4e), and 4-aacetylaminofluorene (4j), were obtained by the trans-t-butylations of 3.Although we attempted to synthesize 1,8-disubstituted fluorene from 3,6-di-t-butylfluorene (2) which was derived from 2,2'-diiodo-4,4'-di-t-butyldiphenylmethane (5), by the same methods, we obtained only 2,7-disubstituted fluorene derivatives (8); it turned out electrophilic substitutions of 2 gave 2,7-disubstituted 3,6-di-t-butylfluorene derivatives.