M-Terphenyl

m-Terphenyl
Names
IUPAC name
1,3-diphenylbenzene
Other names
m-Terphenyl; 1,1'-Biphenyl, 3-phenyl-; 1,1':3',1''-Terphenyl; 1,3-Diphenylbenzene; 1,3-Terphenyl; AI3-00860; CCRIS 1656; EINECS 202-122-1; HSDB 2537; Isodiphenylbenzene; m-Diphenylbenzene; m-Triphenyl; NSC 6808; Santowax M; UNII-WOI2PSS0KX
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.930 Edit this at Wikidata
EC Number
  • 202-122-1
  • InChI=1S/C18H14/c1-3-8-15(9-4-1)17-12-7-13-18(14-17)16-10-5-2-6-11-16/h1-14H
    Key: YJTKZCDBKVTVBY-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C2=CC(=CC=C2)C3=CC=CC=C3
Properties
C18H14
Molar mass 230.310 g·mol−1
Appearance yellow needles
Density 1.23
Melting point 86–87 °C (187–189 °F; 359–360 K)
Boiling point 365
1.51 mg/l
Hazards
GHS labelling:[1]
GHS09: Environmental hazard
Warning
H410
P273, P391, P501
Flash point 191 °C (376 °F; 464 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

m-Terphenyls (also known as meta-terphenyls, meta-diphenylbenzenes, or meta-triphenyls) are organic molecules composed of two phenyl groups bonded to a benzene ring in the one and three positions.[2] The simplest formula is C18H14, but many different substituents can be added to create a diverse class of molecules.[3] Due to the extensive pi-conjugated system, the molecule it has a range of optical properties and because of its size, it is used to control the sterics in reactions with metals and main group elements.[4] This is because of the disubstituted phenyl rings, which create a pocket for molecules and elements to bond without being connected to anything else.[5] It is a popular choice in ligand, and the most chosen amongst the terphenyls because of its benefits in regards to sterics.[6] Although many commercial methods exist to create m-terphenyl compounds, they can also be found naturally in plants such as mulberry trees.[7]

The basic structure of m-terphenyl with R representing the most common bonding site
  1. ^ "M-Terphenyl". pubchem.ncbi.nlm.nih.gov.
  2. ^ Chattaway, Frederick; Evans, R (1896). "LXII. The Diphenylbenzenes. I. Metaphenylbenzene". Journal of the Chemical Society, Transactions. 69: 980–985. doi:10.1039/CT8966900980.
  3. ^ Du, Chi Jen Frank; Hart, Harold; Ng, Kwok Keung Daniel (1986). "A one-pot synthesis of m-terphenyls, via a two-aryne sequence". The Journal of Organic Chemistry. 51 (16): 3162–3165. doi:10.1021/jo00366a016. ISSN 0022-3263.
  4. ^ Adrio, Luis A.; Míguez, José M. Antelo; Hii, King Kuok (Mimi) (2009-09-24). "Synthesis of Terphenyls". Organic Preparations and Procedures International. 41 (5): 331–358. doi:10.1080/00304940903163632. ISSN 0030-4948. S2CID 98582754.
  5. ^ Schultz, Guslav (1874). "Ueber Diphenyl". Justus Liebig's Annalen der Chemie (in German). 174 (2): 201–235. doi:10.1002/jlac.18741740206.
  6. ^ Rivard, Eric; Power, Philip P. (2007-11-01). "Multiple Bonding in Heavier Element Compounds Stabilized by Bulky Terphenyl Ligands". Inorganic Chemistry. 46 (24): 10047–10064. doi:10.1021/ic700813h. ISSN 0020-1669. PMID 17975890.
  7. ^ Liu, Ji-Kai (2006-06-01). "Natural Terphenyls: Developments since 1877". Chemical Reviews. 106 (6): 2209–2223. doi:10.1021/cr050248c. ISSN 0009-2665. PMID 16771447.