Terphenyl

Last updated
para-Terphenyl
Para-terphenyl.png
Para-terphenyl-from-xtal-view-2-3D-bs-17.png
Names
Preferred IUPAC name
11,21:24,31-Terphenyl [1]
Other names
1,1′:4′,1″-Terphenyl [1]
p-Terphenyl
1,4-Diphenylbenzene
para-Diphenylbenzene
p-Diphenylbenzene
para-Triphenyl
p-Triphenyl
Identifiers
3D model (JSmol)
1908447
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.043.146 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-205-2
PubChem CID
RTECS number
  • WZ6475000
UNII
  • InChI=1S/C18H14/c1-3-7-15(8-4-1)17-11-13-18(14-12-17)16-9-5-2-6-10-16/h1-14H X mark.svgN
    Key: XJKSTNDFUHDPQJ-UHFFFAOYSA-N X mark.svgN
  • (para):InChI=1/C18H14/c1-3-7-15(8-4-1)17-11-13-18(14-12-17)16-9-5-2-6-10-16/h1-14H
    Key: XJKSTNDFUHDPQJ-UHFFFAOYAJ
  • C1=CC=C(C=C1)C2=CC=C(C=C2)C3=CC=CC=C3
  • (para):c1ccc(cc1)c2ccc(cc2)c3ccccc3
Properties
C18H14
Molar mass 230.310 g·mol−1
AppearanceWhite powder [2]
Density 1.24 g/cm3
Melting point 212 to 214 °C (414 to 417 °F; 485 to 487 K) [2]
212-213 °C [3]
Boiling point 389 °C (732 °F; 662 K) [3]
Insoluble [2]
1.65 [4]
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H315, H319, H335, H400
P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 207 °C (405 °F; 480 K) [3]
NIOSH (US health exposure limits):
PEL (Permissible)
C 9 mg/m3 (1 ppm) [5] [6] [7]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Terphenyls are a group of closely related aromatic hydrocarbons. Also known as diphenylbenzenes or triphenyls, they consist of a central benzene ring substituted with two phenyl groups. There are three substitution patterns: ortho-terphenyl, meta-terphenyl, and para-terphenyl. Commercial grade terphenyl is generally a mixture of the three isomers. This mixture is used in the production of polychlorinated terphenyls, which were formerly used as heat storage and transfer agents. [2]

Contents

p-Terphenyl derivatives are found in various fungi and bacteria. One example is atromentin, a pigment found in some mushrooms. These natural p-terphenyls are better described as diphenylquinones or diphenylhydroquinones. Some m-terphenyl compounds occur in plants. [8]

See also

Related Research Articles

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<span class="mw-page-title-main">Toluene diisocyanate</span> Chemical compound

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<i>p</i>-Xylene Chemical compound

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<i>o</i>-Xylene Chemical compound

o-Xylene (ortho-xylene) is an aromatic hydrocarbon with the formula C6H4(CH3)2, with two methyl substituents bonded to adjacent carbon atoms of a benzene ring (the ortho configuration). It is a constitutional isomer of m-xylene and p-xylene, the mixture being called xylene or xylenes. o-Xylene is a colourless slightly oily flammable liquid.

<i>m</i>-Cresol Chemical compound

meta-Cresol, also 3-methylphenol, is an organic compound with the formula CH3C6H4(OH). It is a colourless, viscous liquid that is used as an intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and o-cresol.

<i>m</i>-Xylene Chemical compound

m-Xylene (meta-xylene) is an aromatic hydrocarbon. It is one of the three isomers of dimethylbenzene known collectively as xylenes. The m- stands for meta-, indicating that the two methyl groups in m-xylene occupy positions 1 and 3 on a benzene ring. It is in the positions of the two methyl groups, their arene substitution pattern, that it differs from the other isomers, o-xylene and p-xylene. All have the same chemical formula C6H4(CH3)2. All xylene isomers are colorless and highly flammable.

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1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of benzene, consisting of two adjacent chlorine atoms.

Perchloryl fluoride is a reactive gas with the chemical formula ClO
3F. It has a characteristic sweet odor that resembles gasoline and kerosene. It is toxic and is a powerful oxidizing and fluorinating agent. It is the acid fluoride of perchloric acid.

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Divinylbenzene (DVB) is an organic compound with the chemical formula C6H4(CH=CH2)2 and structure H2C=CH−C6H4−HC=CH2. It is related to styrene by the addition of a second vinyl group. It is a colorless liquid manufactured by the thermal dehydrogenation of isomeric diethylbenzenes. Under synthesis conditions, o-divinylbenzene converts to naphthalene and thus is not a component of the usual mixtures of DVB.

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<i>o</i>-Anisidine Chemical compound

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ortho-Cresol (IUPAC name: 2-methylphenol, also known as 2-hydroxytoluene or ortho-Toluenol) is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and m-cresol.

Dinitro-<i>ortho</i>-cresol Chemical compound

Dinitro-ortho-cresol (DNOC) is an organic compound with the structural formula CH3C6H2(NO2)2OH. It is a yellow solid that is only slightly soluble in water. It is extremely toxic to humans and was previously used as a herbicide and insecticide.

3-Nitrotoluene or meta-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is one of three isomers of nitrotoluene. A yellow liquid, it is used in the manufacture of meta-toluidine, which is an intermediate in the production of various dyes.

2-Nitrotoluene or ortho-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is pale yellow liquid that crystallizes in two forms, called α (−9.27 °C) and β (−3.17 °C). It is mainly a precursor to o-toluidine, which is an intermediate in the production of various dyes.

References

  1. 1 2 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 345. doi:10.1039/9781849733069-00130. ISBN   978-0-85404-182-4.
  2. 1 2 3 4 p-Terphenyl at chemicalland21.com
  3. 1 2 3 p-Terphenyl at Sigma-Aldrich
  4. ↑ "Organic molecular single crystals". cryos-beta.kharkov.ua.
  5. ↑ NIOSH Pocket Guide to Chemical Hazards. "#0591". National Institute for Occupational Safety and Health (NIOSH).
  6. ↑ NIOSH Pocket Guide to Chemical Hazards. "#0592". National Institute for Occupational Safety and Health (NIOSH).
  7. ↑ NIOSH Pocket Guide to Chemical Hazards. "#0593". National Institute for Occupational Safety and Health (NIOSH).
  8. ↑ Liu, Ji-Kai (2006). "Natural Terphenyls: Developments since 1877". Chemical Reviews. 106 (6): 2209–2223. doi:10.1021/cr050248c. PMID   16771447.
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