15810-15-8

Basic information

• Product Name: 9,10-DibromoPhenanthrene
• Synonyms: 9,10-DibromoPhenanthrene;Phenthren-9-ylaMine
• CAS NO: 15810-15-8
• Molecular Formula: C₁₄H₈Br₂
• Molecular Weight: 336.02132
• Mol File: 15810-15-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 179-180℃ (heptane )
• Boiling Point: 441.1±18.0 °C(Predicted)
• Appearance: /
• Density: 1.768±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 9,10-DibromoPhenanthrene(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-DibromoPhenanthrene(15810-15-8)
• EPA Substance Registry System: 9,10-DibromoPhenanthrene(15810-15-8)

Safety Data

• Hazardous Substances Data: 15810-15-8(Hazardous Substances Data)

Usage

General Description

9,10-DibromoPhenanthrene is a chemical compound with the molecular formula C14H8Br2. It is a brominated derivative of phenanthrene, which is a polycyclic aromatic hydrocarbon. 9,10-DibromoPhenanthrene is a white to light brown powder that is sparingly soluble in water but soluble in organic solvents. It is commonly used as a building block in organic synthesis and as a starting material for the production of various pharmaceuticals, agrochemicals, and dyes. It is also being studied for its potential use in the development of new materials and as a tool for chemical research. The compound is known to have moderate to high levels of toxicity, and appropriate safety measures should be taken when handling it.

Upstream product

• 85-01-8 phenanthrene 
• 92161-37-0 2,2′‐bis(dibromomethyl)‐1,1′‐biphenyl 
• 605-39-0 2,2'-dimethyl-1,1'-biphenyl 
• 1091603-62-1 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenanthrene 
• 17024-21-4 9-Bromo-10-nitrophenanthrene 
• 36262-79-0 phenanthro[9,10-d][1,2,3]triazol-1-ylamine 

Downstream Products

• 1288982-08-0 9,10-bis(trimethylsilyl)phenanthrene 
• 151161-86-3 9,10-phenanthraquinone 

Relevant articles and documents

Donor-acceptor substituted benzo-, naphtho- and phenanthro-fused norbornadienes

The photochromic norbornadiene/quadricyclane (NBD/QC) couple has found interest as a molecular solar thermal energy (MOST) system for storage of solar energy. To increase the energy difference between the two isomers, we present here the synthesis of a selection of benzo-fused NBD derivatives that contain an aromatic unit, benzene, naphthalene or phenanthrene, fused to one of the NBD double bonds, while the carbon atoms of the other double bond are functionalized with donor and acceptor groups. The synthesis protocols involve functionalization of benzo-fused NBDs with bromo/chloro substituents followed by a subjection of these intermediates to a cyanation reaction (introducing a cyano acceptor group) followed by a Sonogashira coupling (introducing an arylethynyl donor group, -C≡CC6H4NMe2 or -C≡CC6H4OMe). While the derivatives have good absorption properties in the visible region (redshifted relative to parent system) in the context of MOST applications, they lack the ability to undergo NBD-to-QC photoisomerization, even in the presence of a photosensitizer. It seems that loss of aromaticity of the fused aromatics is too significant to allow photoisomerization to occur. The concept of destroying aromaticity of a neighboring moiety as a way to enhance the energy density of the NBD/QC couple thus needs further structural modifications, in the quest for optimum MOST systems.

Simultaneous expansion of 9,10 boron-doped anthracene in longitudinal and lateral directions

Doubly boron-doped anthracenes and pentacenes have been longitudinally and laterally expanded through annulation of thiophene or benzene rings. The obtained series of closely related compounds allowed an assessment of key structure-property relationships with a focus on optoelectronic characteristics. Most of the products are benchtop-stable blue emitters and capable of accepting two electrons in a reversible manner. The syntheses involved late-stage modifications through photocyclization or stepwise oxidative C-C coupling (DDQ/BF3·Et2O) as well as cyclocondensation of ortho-disilylated or -diborylated aryl building blocks.