474918-32-6

Basic information

• Product Name: 2-Bromo-9,9-diphenylfluorene
• Synonyms: 9H-Fluorene, 2-bromo-9,9-diphenyl-;2-bromo-9,9-diphenylfluorene;2-bromo-9,9-diphenyl-fluororene;2-Bromo-9,5-diphenylfluorene;2--9,9--;2-Dibromo-9,9-diphenylfluorene;2-Bromo-9,9-diphenyl;2-BroMo-9,9-diphenyl-9H-fluorene
• CAS NO: 474918-32-6
• Molecular Formula: C₂₅H₁₇Br
• Molecular Weight: 397.31
• EINECS: 1312995-182-4
• Product Categories: Fluorene Derivatives;OLED materials,pharm chemical,electronic
• Mol File: 474918-32-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 217.0 to 221.0 °C
• Boiling Point: 480.5 °C at 760 mmHg
• Flash Point: 235.7 °C
• Appearance: /
• Density: 1.363 g/cm³
• Refractive Index: 1.681
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Toluene
• CAS DataBase Reference: 2-Bromo-9,9-diphenylfluorene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-9,9-diphenylfluorene(474918-32-6)
• EPA Substance Registry System: 2-Bromo-9,9-diphenylfluorene(474918-32-6)

Safety Data

• Hazardous Substances Data: 474918-32-6(Hazardous Substances Data)

Usage

Uses

2-Bromo-9,9-dimethylfluorene is a fluorene derivative which shows π-electron conjugation. It has a high fluorescent and high electron delocalization. It can be used as a non-linear optical (NLO) material. 2-bromo-9, 9-diphenylfluorene can be synthesized by using 2-bromofluorene and iodomethane as the major reactants. It can be majorly used in organic electronic based applications.

Description

2-bromo-9, 9-diphenylfluorene appears as an off-white solid. It belongs to the fluorene group compound. It is a kind of OLED (organic light-emitting diodes) intermediate. It can be used for the production of 9, 9-diphenylfluorene-capped oligothiophenes which can be used as active materials such as filed-effect transistors and light-emitting diodes.

Chemical Properties

off-white powder

Synthesis

10 g (30 mmol) of 2-bromo-9-phenyl-9H-fluoren-9-ol was dissolved in 60 ml of benzene, and 2.4 ml (45 mmol) of concentrated sulfuric acid diluted with a small amount of benzene was added to the solution. The mixture was stirred for 5 hours at 80° C, and after evaporating the benzene, 1 N sodium hydroxide solution was added to the remaining solution to a pH of around 7. The mixture was extracted 3 times with ethyl acetate (40 ml). The collected organic layer was dried with magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography. 6 g of Intermediate N (yield: 50%).

References

(2015). Synthesis method of 2-bromo-9, 9-diphenylfluorene, Google Patents. Wong, Ken-Tsung, et al. "Synthesis and properties of novel thiophene-based conjugated homologues: 9, 9-diphenylfluorene-capped oligothiophenes."Organic letters 4.25 (2002): 4439-4442.

InChI:InChI=1/C25H17Br/c26-20-15-16-22-21-13-7-8-14-23(21)25(24(22)17-20,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H

Upstream product

• 3096-56-8 2-bromofluoren-9-one 
• 71-43-2 benzene 
• 17103-26-3 methyl 4'-bromo-[1,1'-biphenyl]-2-carboxylate 
• 100-58-3 phenylmagnesium bromide 
• 486-25-9 9-fluorenone 
• 108-86-1 bromobenzene 
• 736928-22-6 2-bromo-9-phenyl-9-hydroxyfluorene 

Downstream Products

• 462128-39-8 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-diphenyl-9H-fluorene 
• 1158844-76-8 C₃₁H₂₂ 
• 1610059-33-0 C₇₇H₇₁N₃ 
• 400607-31-0 (9,9-diphenyl-9H-fluoren-2-yl)boronic acid 

Relevant articles and documents

Preparation method 2 -amino -9-9 - diphenyl fluorene

The invention discloses a preparation method of 2 - amino -9 and 9 - diphenyl fluorene, which comprises the following steps: taking 9 - fluorenone as a raw material, and carrying out bromination reaction to obtain 2 - bromo -9 - fluorenone. 2 - Bromo -9 - fluorenone and bromobenzene formative reagent are reacted to obtain 2 - bromo -9 - phenyl -9 - hydroxyl - fluorene. 2 - Bromo -9 - phenyl -9 - hydroxy - fluorene was subjected to an alkylation reaction with benzene to give 2 - bromo -9, 9 - diphenylfluorene. 2 - Bromo -9, 9 - diphenylfluorene and cuprous oxide, palladium acetate (II) and N - methylpyrrolidinone were reacted in liquid ammonia to give 2 - amino -9, 9 - diphenylfluorene. The preparation method is used for preparing 2 - amino -9 and 9 - diphenylfluorene, the used preparation is easy to obtain, the technological process is simple, the product yield is high, the production cost is reduced, 2 - amino -9 and 9 - diphenyl fluorene are produced.

A 2 - bromo - 9, 9 - diphenyl wu synthetic method

The invention discloses a synthetic method of 2-bromo-9,9-diphenyl fluorene. The synthetic method comprises the following steps: (1) mixing trifluoroacetic acid, aluminium chloride anhydrous and benzene in a molar ratio to obtain A liquid; (2) mixing 2-bromo-9-phenyl-fluoren-9-ol and benzene in a molar ratio to obtain B liquid; (3) under gas shield, mixing the A liquid and the B liquid in proportion while stirring, and controlling the system temperature to be not over 50 DEG C at the same time; (4) raising the temperature to be 65-75 DEG C, reacting for 1-1.5 h, supplementing trifluoroacetic acid, and continuously reacting for 2-4 h; and (5) separating and purifying to obtain the 2-bromo-9,9-diphenyl fluorene. The synthetic method is simple in operation and mild in reaction condition, has higher yield and lower cost, and has wide industrial popularization prospect.

DERIVATIVES OF 2-DIARYLAMINOFLUORENE AND ORGANIC ELECTRONIC COMPOUNDS CONTAINING THEM

The present invention relates to certain fluorenes, to the use of the compounds in an electronic device, and to an electronic device comprising at least one of these compounds. The present invention furthermore relates to a process for the preparation of the compounds and to a formulation and composition comprising one or more of the compounds.