55135-66-5

Basic information

• Product Name: 9-Bromo-9-phenylfluorene
• Synonyms: 9-BROMO-9-PHENYL-9H-FLUORENE;9-BROMO-9-PHENYLFLUORENE;AKOS 91526;9-Bromo-9-phenylfluorene,97%;9-Bromo-9-phenylfluorene ,98%;9-Phenylfluorenyl BroMide;NSC 28079;(9-Bromo-9H-fluoren-9-yl)benzene
• CAS NO: 55135-66-5
• Molecular Formula: C₁₉H₁₃Br
• Molecular Weight: 321.21
• EINECS: -0
• Product Categories: Aromatics Compounds;Fluorenes;Fluorenes & Fluorenones;Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Chiral Compound;Aromatics;Aryl;C13 to C37+;Halogenated Hydrocarbons;Intermediates
• Mol File: 55135-66-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 99-101 °C(lit.)
• Boiling Point: 394.324 °C at 760 mmHg
• Flash Point: 172.533 °C
• Appearance: /
• Density: 1.426 g/cm³
• Vapor Pressure: 1.73E-06mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water
• BRN: 2561445
• CAS DataBase Reference: 9-Bromo-9-phenylfluorene(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Bromo-9-phenylfluorene(55135-66-5)
• EPA Substance Registry System: 9-Bromo-9-phenylfluorene(55135-66-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 55135-66-5(Hazardous Substances Data)

Usage

Description

9-Bromo-9-phenylfluorene is a yellow crystalline solid that is known for its solvolysis properties, which proceed via a limiting SN1 mechanism. This organic compound is characterized by the presence of a bromine atom at the 9-position and a phenyl group at the 9-phenyl position on a fluorene backbone.

Uses

Used in Chemical Synthesis:
9-Bromo-9-phenylfluorene is used as a chemical intermediate for the synthesis of various organic compounds, including:
N-(9-(9-phenylfluorenyl))-L-alaninal: 9-Bromo-9-phenylfluorene is utilized in the development of complex organic molecules and has potential applications in the pharmaceutical industry.
N-(9-phenylfluoren-9-yl)-L-serine: This molecule is an important building block in the synthesis of peptides and other biomolecules, with potential applications in drug discovery and development.
1-hydroxypyrazoles protected at the oxygen atom: These molecules are used in the synthesis of various heterocyclic compounds, which have a wide range of applications in the chemical and pharmaceutical industries.
Used in Bulky Amine Protecting Reagent:
9-Bromo-9-phenylfluorene is also used as a bulky amine protecting reagent, which is reported to be 6000 times more stable to acid than the trityl group. This property makes it a valuable tool in organic synthesis, particularly in the protection of amine groups during chemical reactions, allowing for selective deprotection under acidic conditions without affecting the protected amine.

InChI:InChI=1/C19H13Br/c20-17-12-6-11-16-14-9-4-5-10-15(14)18(19(16)17)13-7-2-1-3-8-13/h1-12,18H

Upstream product

• 789-24-2 9-Phenylfluorene 
• 108-86-1 bromobenzene 
• 486-25-9 9-fluorenone 
• 76-84-6 triphenylmethyl alcohol 
• 7726-95-6 bromine 
• 506-96-7 Acetyl bromide 
• 25603-67-2 9-phenyl-fluoren-9-ol 

Downstream Products

• 102593-53-3 ethyl 10-phenylphenanthrene-9-carboxylate 
• 147912-84-3 (S)-N-(9-phenylfluoren-9-yl)-o-bromophenylalanine 
• 125229-20-1 (2S,3R)-3-Allyloxymethyl-1-(9-phenyl-9H-fluoren-9-yl)-aziridine-2-carboxylic acid methyl ester 
• 120230-62-8 dimethyl (S)-N-(9-phenyl-9H-fluoren-9-yl)aspartate 
• 128576-61-4 1-(tert-butyl) 4-methyl N-benzyl-N-(9-phenyl-9H-fluoren-9-yl)-L-aspartate 
• 128576-73-8 (2S)-4-benzyl 1-methyl N-benzyl-N-(9-phenylfluoren-9-yl)aspartate 
• 128599-28-0 (2S)-4-benzyl 1-tert-butyl N-benzyl-N-(9-phenylfluoren-9-yl)aspartate 
• 95407-38-8 N-<2-(methoxycarbonyl)ethyl>-N-(9-phenylfluorenyl)-3-cyanoalanine benzyl ester 
• 105519-71-9 (S)-N-[9-(9-phenylfluorenyl)]alanine 
• 147698-07-5 (S)-2-hexanedioic acid γ-methyl ester 
• 147698-06-4 1-tert-Butyl 6-methyl (S)-2-[N-(9-phenylfluoren-9-yl)amino]hexandioate 
• 147912-65-0 methyl 2--3-(2-bromophenyl)propanoate 
• 147912-68-3 methyl 2--3-(2-bromo-3,4-dimethoxyphenyl)propanoate 
• 147912-66-1 methyl 2--3-(2-bromo-4,5-dimethoxyphenyl)propanoate 

Relevant articles and documents

Synthesis of Kainoids and C4 Derivatives

A unified stereoselective synthesis of 4-substituted kainoids is reported. Four kainic acid analogues were obtained in 8-11 steps with up to 54% overall yields. Starting from trans-4-hydroxy-l-proline, the sequence enables a late-stage modification of C4 substituents with sp2 nucleophiles. Stereoselective steps include a cerium-promoted nucleophilic addition and a palladium-catalyzed reduction. A 10-step route to acid 21a was also established to enable ready functionalization of the C4 position.

Fluorene-based organic compound and application thereof on OLED device

The invention relates to a fluorene-based organic compound and application thereof on an OLED device. A structure of the compound is that fluorine is connected with a hexatomic ring structure of a benzo hexatomic ring through a carbon-carbon bond, so that material chemical stability is improved and active positions of a branch chain radical are prevented from being exposed through the carbon-carbon bond connection; the whole molecule is a relatively great rigid structure, and has relatively high triplet-state energy level (T1); moreover, steric hindrance is great, rotation is not liable to occur and the three-dimensional space structure is more stable, so that the compound has a relatively high glass transition temperature and relatively high molecule thermal stability; besides, distribution positions of HOMO and LUMO of the compound are separated from each other, so that the fluorene-based organic compound has proper HOMO and LUMO energy level; and after the compound is applied to theOLED device, light-emitting efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.

Alkyl substituent effects on pipecolyl amide isomer equilibrium: Efficient methodology for synthesizing enantiopure 6-alkylpipecolic acids and conformational analysis of their N-acetyl N'-methylamides

Enantiopure 6-alkylpipecolic acid hydrochlorides 1a-e were synthesized in five steps and 15-59% overall yields from α-tert-butyl β-methyl N- (PhF)aspartate (3) via an approach featuring selective hydride reduction to the corresponding aspartate β-aldehyde 2, aldol condensations with the enolates of various methyl alkyl ketones, and diastereoselective intramolecular reductive aminations. The influence of the 6-position substituent on the equilibrium and the energy barrier for isomerization of the amide N-terminal to pipecolate was then explored via the synthesis of N- acetyl N'-methylpipecolinamide (16) and its (2S,6R)-6-tert- butylpipecolinamide counterpart 17, and their conformational analysis by proton NMR spectroscopy and coalescence experiments. The presence of the tert-butyl substituent augmented the population of the amide cis-isomer and lowered the barrier for pipecolyl amide isomerization in water. Compared with the results from our previous examination of N-acetyl-5-tert-butylproline N'- methylamides (Beausoleil, E.; Lubell, W. D. J. Am. Chem. Soc. 1996, 118, 12902), the consequences of the bulky 6-alkyl substituent on the acetamide geometry and isomerization barrier were less pronounced in the pipecolate series relative to the respective proline amides.