Wikipedia

Terphenyl

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]

para-Terphenyl
Skeletal formula of para-terphenyl
Ball-and-stick model of para-terphenyl
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 Edit this at Wikidata
EC Number
  • 202-205-2
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 ☒N
    Key: XJKSTNDFUHDPQJ-UHFFFAOYSA-N ☒N
  • (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
Appearance White 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[4]
Boiling point 389 °C (732 °F; 662 K)[4]
Insoluble[2]
1.65[3]
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
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 four-colored diamondHealth 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)[4]
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).
☒N verify (what is checkY☒N ?)

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]

  • ortho-Terphenyl
    ortho-Terphenyl
  • meta-Terphenyl
    meta-Terphenyl
  • para-Terphenyl
    para-Terphenyl

See also

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References

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  1. ^ a b 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. ^ a b c d p-Terphenyl at chemicalland21.com
  3. ^ "Organic molecular single crystals". cryos-beta.kharkov.ua.
  4. ^ a b c p-Terphenyl at Sigma-Aldrich
  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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