18631-82-8

Basic information

• Product Name: 1,2,3,4,5-pentaphenylbenzene
• CAS NO: 18631-82-8
• Molecular Formula: C₃₆H₂₆
• Molecular Weight: 458.602
• Mol File: 18631-82-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 516.2°Cat760mmHg
• Flash Point: 269.6°C
• Density: 1.102g/cm³
• CAS DataBase Reference: 1,2,3,4,5-pentaphenylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,5-pentaphenylbenzene(18631-82-8)
• EPA Substance Registry System: 1,2,3,4,5-pentaphenylbenzene(18631-82-8)

Safety Data

• Hazardous Substances Data: 18631-82-8(Hazardous Substances Data)

Usage

Chemical structure

A polycyclic aromatic hydrocarbon composed of five phenyl rings attached to a central benzene ring.

Applications

a. Organic synthesis
b. Materials science
c. Organic semiconductors
d. Fluorescent dye in imaging applications

Symmetrical

The compound has a symmetrical structure with five phenyl rings attached to a central benzene ring.

Rigid

The structure is rigid due to the multiple carbon-carbon bonds in the aromatic rings.

Significance in organic chemistry and materials science

Its unique structure and properties make it a valuable building block for constructing larger molecules and materials with specific properties.

Upstream product

• 932-87-6 1-Bromo-2-phenylacetylene 
• 536-74-3 phenylacetylene 
• 501-65-5 diphenyl acetylene 
• 855265-97-3 7-benzyl-1,2,3,4,5-pentaphenyl-norborn-2-en-7-ol 

Relevant articles and documents

Organic and organometallic derivatives of pentaphenylbenzene, C 6Ph5X: Correlation of peripheral phenyl ring orientations with the steric bulk of "x"

A series of C6Ph5X compounds, including X = H, Br, CO2H, CO2R, CCPh, cis-BrC=C(Br)Ph, 2-bornenyl, and ferrocenyl, have been characterized by use of X-ray crystallography. Also, the first organometallic complexes of pentaphenylbenzene have been prepared by reaction with chromium hexacarbonyl to yield (η6-C 6Ph5H)Cr(CO)3 complexes in which the metal tripod is attached either to an ortho peripheral ring or to the central ring. Crystalline pentaphenylbenzoic acid exists as a hydrogen-bonded dimer; however, the steric bulk of the substituents does not allow the carboxylic acid moieties to be linked directly but instead via two bridging methanol molecules. In the solid state, the orientation of the peripheral rings in bulky C 6Ph5X systems is very sensitive to the size of the "X" substituents, such that the twist angle of the para ring responds inversely with increasing bulk of "X", which drives the ortho rings farther out of the plane of the central ring. The relevance of these observations to correlated motion in molecular propellers, and ultimately to molecular machines, is discussed.

OBSERVATIONS AND COMMENTS ON THE THERMAL BEHAVIOR OF 7-SILANORBORNADIENES

Evidence for a radical mechanism in the termal decomposition of a 7-silanorbornadiene is presented.It is demonstrated that 2-carboxy-7-silanorbornadienes undergo a formal 1,5-migration of silicon to form O-silyl enol ethers.An earlier suggested rearrangement of a 7-silanorbornadiene to a silepin or silanorcardiene is excluded.A recent report of thermal and photochemical epimerization of 7-silanorbornadienes is shown to be incorrect.