16716-13-5

Basic information

• Product Name: M-QUINQUEPHENYL
• Synonyms: 1,1':3',1'':3'',1''':3''',1''''-Quinquephenyl;m-Quinquiphenyl;M-QUINQUEPHENYL;1,1':3',1'':3'',1''':3''',1''''-Quinquebenzene;1,3-Bis(biphenyl-3-yl)benzene
• CAS NO: 16716-13-5
• Molecular Formula: C₃₀H₂₂
• Molecular Weight: 382.5
• EINECS: 240-774-9
• Mol File: 16716-13-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 97-98 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• Boiling Point: 567.7°Cat760mmHg
• Flash Point: 296.7°C
• Appearance: /
• Density: 1.091g/cm³
• Vapor Pressure: 2.56E-12mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: M-QUINQUEPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: M-QUINQUEPHENYL(16716-13-5)
• EPA Substance Registry System: M-QUINQUEPHENYL(16716-13-5)

Safety Data

• Hazardous Substances Data: 16716-13-5(Hazardous Substances Data)

Usage

General Description

M-QUINQUEPHENYL is a chemical compound with the molecular formula C29H22. It is a polycyclic aromatic hydrocarbon that consists of five phenyl rings connected by carbon-carbon single bonds. M-QUINQUEPHENYL is a stable, non-reactive solid at room temperature and is used in organic synthesis as a building block for the construction of more complex organic molecules. It has potential applications in the development of materials such as liquid crystals, conductive polymers, and organic semiconductors. M-QUINQUEPHENYL is also being studied for its potential use in organic light-emitting diodes (OLEDs) and other electronic devices. However, due to its aromatic nature, M-QUINQUEPHENYL may pose health and environmental risks if not handled and disposed of properly.

InChI:InChI=1/C30H22/c1-3-10-23(11-4-1)25-14-7-16-27(20-25)29-18-9-19-30(22-29)28-17-8-15-26(21-28)24-12-5-2-6-13-24/h1-22H

Upstream product

• 108-36-1 1,3-dibromobenzene 
• 19821-80-8 1,3-dibromo-2-iodo-benzene 
• 103068-18-4 [(1,1'-biphenyl)-3-yl]magnesium bromide 
• 20442-79-9 3-iodo-1,1'-biphenyl 
• 97923-51-8 1,3-Bis-<3-oxo-5-phenyl-cyclohex-4-enyl>-benzol 
• 2113-57-7 3-bromobiphenyl 
• 196212-27-8 4,4,5,5-tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,2-dioxaborolane 
• 58258-94-9 3,3'-(1,3-phenylene)-bis(1-phenyl-2-propene-1-one) 
• 591-19-5 m-Bromoaniline 
• 619-45-4 4-methoxycarbonyl aniline 
• 78626-83-2 2''-nitro-m-quinquephenyl 
• 3282-10-8 methyl 3,5-dibromo-4-aminobenzoate 
• 13402-32-9 1,3-dibromo-2-nitrobenzene 
• 4123-72-2 4-amino-3,5-dibromobenzoic acid 

Downstream Products

• 127131-73-1 1,3-Bis-(3-phenyl-cyclohexa-1,4-dienyl)-benzene 

Relevant articles and documents

A low-temperature polymorph of m-quinquephenyl

A low-temperature polymorph of 1,1′:3′,1′′: 3′′,1′′′:3′′′, 1′′′′-quinquephenyl (m-quinquephenyl), C30H22, crystallizes in the space group P21/c with two molecules in the asymmetric unit. The crystal is a three-component nonmerohedral twin. A previously reported room-temperature polymorph [Rabideau, Sygula, Dhar & Fronczek (1993). Chem. Commun. pp. 1795-1797] also crystallizes with two molecules in the asymmetric unit in the space group P . The unit-cell volume for the low-temperature polymorph is 4120.5(4)A3, almost twice that of the room-temperature polymorph which is 2102.3(6)A3. The molecules in both structures adopt a U-shaped conformation with similar geometric parameters. The structural packing is similar in both compounds, with the molecules lying in layers which stack perpendicular to the longest unit-cell axis. The molecules pack alternately in the layers and in the stacked columns. In both polymorphs, the only interactions between the molecules which can stabilize the packing are very weak C-H...π interactions.

A One-Pot Synthesis of m-Terphenyls via a Two-Aryne Sequence

Aryl-Grignards (3+ equiv) react with 2,6-dibromoiodobenzene or other 1,2,3-trihalobenzenes to give 2,6-diarylphenylmagnesium halides.The mechanism involves Grignard exchange at the central halogen, followed by two cycles of magnesium halide loss and regioselective capture of the resulting aryne by the aryl-Grignard reagent (Scheme I).Typical examples are shown in Table I.The method is especially applicable to m-terphenyls in which the "outer" rings are identical and/or in which substitution at the 2' or other positions of the "central" ring is desired.

Polyphenyl synthesis by means of the Kharash-type Grignard cross-coupling reaction

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