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

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

Uses

Used in Organic Synthesis:
M-QUINQUEPHENYL is utilized as a key building block in organic synthesis, contributing to the creation of complex organic molecules. Its structural properties make it a versatile component in the synthesis of a wide range of compounds.
Used in Material Development:
In the field of material development, M-QUINQUEPHENYL is employed for its potential in creating advanced materials such as liquid crystals, conductive polymers, and organic semiconductors. Its unique structure and properties lend themselves to the enhancement of these materials' performance.
Used in Electronic Devices:
M-QUINQUEPHENYL is also being explored for its application in electronic devices, particularly in organic light-emitting diodes (OLEDs). Its incorporation into these devices can potentially improve their efficiency and performance.
Used in Research and Development:
Due to its aromatic nature, M-QUINQUEPHENYL is a subject of ongoing research and development. Scientists are investigating its properties and potential applications further, with the aim of harnessing its capabilities in various industries.

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

• 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 
• 108-36-1 1,3-dibromobenzene 
• 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 
• 608-30-0 2,6-dibromoaniline 
• 103068-18-4 [(1,1'-biphenyl)-3-yl]magnesium bromide 
• 97923-51-8 1,3-Bis-<3-oxo-5-phenyl-cyclohex-4-enyl>-benzol 
• 78626-84-3 2''-amino-m-quinquephenyl 

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.

Acyclic, Linear Oligo-meta-phenylenes as Multipotent Base Materials for Highly Efficient Single-layer Organic Light-emitting Devices

Oligo-meta-phenylenes have been designed and synthesized as multipotent base materials of single-layer organic light-emitting devices. Simple molecular structures of oligo-meta-phenylenes composed of linear phenylene arrays benefited from the wealth of modern reactions available for biaryl couplings and were concisely synthesized in a series. Structure-performance relationship studies with the first seven congeners revealed key features important for the multipotent materials in single-layer devices. As a result, highly efficient phosphorescent electroluminescence was made possible in a highly simplified device architecture comprising one-region, single-layer configurations. Detailed investigations with hole-only devices disclosed that the hole mobility was effectively retarded by potent materials, which should facilitate hole/electron recombination for electroluminescence.

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.

Syntheses and Spectral Properties of Several Branched-chain Polyphenyls containing 1,3,5-Trisubstituted Ring(s)

Six polyphenyls, including four new compounds, 5',5''-di(2-biphenylyl)-2,2'''-diphenyl-m-quaterphenyl (3), 2,5',2''-triphenyl-m-terphenyl (4), 3,5-di(2-biphenylyl)-o-terphenyl (5), and 5''-(3-biphenylyl)-m-quinquephenyl (6), were synthesized by the Ullmann coupling reaction of iodo compounds.Proton magnetic resonance spectral studies indicated that the characteristic spectral features of the polyphenyls containing 1,3,5-trisubstituted ring system(s) were fully compatible with their conformational aspects deduced from stereomodels.Ultraviolet spectral data indicated that the dihedral angle of the pivot bond of the branched ring in the polyphenyls in solution is very similar to that of biphenyl.Keywords - Ullmann reaction; quinquephenyl; sexiphenyl; septiphenyl; decaphenyl; polyphenyl; IR; UV; 1H-NMR

Syntheses and Physical Properties of Several Octiphenyls and a Septiphenyl

Six symmetrical linear octiphenyls were synthesized by the Ullmann homo-coupling reaction of iodoquaterphenyl.Another satisfactory method for synthesizing octiphenyls is also described, i.e., a Kharash-type Grignard cross-coupling of biphenylylmagnesium bromide and diiodoquaterphenyl in the presence of bis(acetylacetonato)nickel(II).Moreover, m-septiphenyl was succesfully synthesized by deamination of the corresponding amino compound.Infrared studies of the polyphenyls indicated that the fine-structure bands in the regions of 770-810 and 870-915 cm-1 may be considered as indicators of the presence of consecutive m-phenylene rings, regardless of the existence of o- or p-phenylene rings.The ultraviolet spectra of the octiphenyls, which contain two kinds of linkages, showed absorption curves closely related to those of quaterphenyls corresponding to the structural units of the former compounds.The nuclear magnetic resonance spectra of the polyphenyls without an o-phenylene ring showed multiplet peaks due to the resonances of an isolated m-phenylene proton at the lowest field within a narrow region (δ 7.81-7.95).Hueckel molecular orbital calculations of the longest wavelength absorption bands of ten polyphenyls were carried out.The calculated and observed wavelengths were in rather good agreement except for the cases of three compounds.Keywords - Ullmann reaction; Ni-complex-catalyzed cross-coupling; octiphenyls; septiphenyls; IR; UV; NMR; MO; quaterphenyl derivatives; polyphenyls

Studies of Polyphenyls and Polyphenylenes. II. The Synthesis and Physical Properties of Polyphenyls Containing Para Linkage

Twelwe linear polyphenyls, including quinque- to octiphenyl, were synthesized by the Ullmann cross-coupling reaction of iodobiphenyl with diiodobenzene or iodoterphenyl.Ultraviolet spectral studies of the polyphenyls indicated that the positions of the K-bands above ca.260 nm, regardless of the presence of o- or m-phenylene unit(s), may be considered to be an indication of the approximate number of consecutive p-phenylene units.Infrared studies also showed that the locations of strong or medium bands in the 815-850 cm-1 region may give the same information.The HMO calculations of the longest wavelength absorption bands of twenty-four polyphenyls were carried out.A comparison between the calculated and observed wavelengths gave rather good agreement, except in the cases of two compounds.The signals of the proton magnetic resonanse spectra of eighteen polyphenyls were assigned tentatively.The correlations between the arrangement of the benzene rings and the spectral patterns are discussed.