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Biphenyl
Identifiers
CAS number 92-52-4 Yes check.svgY
SMILES
Properties
Molecular formula C12H10
Molar mass 154.21 g mol−1
Density 0.992 g/cm3
Melting point

68.93 °C, 342 K, 156 °F

Boiling point

256 °C, 529 K, 493 °F

Solubility in water Insoluble
Hazards
EU Index 601-042-00-8
EU classification Irritant (Xi)
Dangerous for
the environment (N)
R-phrases R36/37/38, R50/53
S-phrases (S2), S23, S60, S61
NFPA 704
NFPA 704.svg
1
1
0
Flash point 113 °C
Autoignition
temperature
540 °C
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Biphenyl (or diphenyl or phenyl benzene or 1,1'-biphenyl or lemonene) is an organic compound that forms colorless crystals. It has a distinctively pleasant smell. Biphenyl is an aromatic hydrocarbon with a molecular formula (C6H5)2. It is notable as a starting material for the production of polychlorinated biphenyls (PCBs), which were once widely used as dielectric fluids and heat transfer agents. Biphenyl is also an intermediate for the production of a host of other organic compounds such as emulsifiers, optical brighteners, crop protection products, and plastics.

Contents

Properties

Biphenyl occurs naturally in coal tar, crude oil, and natural gas and can be produced from these sources by distillation. Biphenyl is insoluble in water, but soluble in typical organic solvents. The biphenyl molecule consists of two connected phenyl rings. Lacking functionalization, it is not very reactive.

Stereochemistry

Rotation about the single bond in biphenyl, and especially its ortho-substituted derivatives, is sterically hindered. For this reason, some substituted biphenyls show atropisomerism; that is, the individual C2-symmetric-isomers are optically stable. Some derivatives, as well as related molecules such as BINAP, find application as ligands in asymmetric synthesis. In the case of unsubstituted biphenyl, the equilibrium torsional angle is 44.4° and the torsional barriers are 6.0 kJ/mol at 0° and 6.5 kJ/mol at 90°.[1]

Biological aspects

Biphenyl prevents the growth of molds and fungus, and is therefore used as a preservative (E230, in combination with E231, E232 and E233), particularly in the preservation of citrus fruits during transportation.

It is mildly toxic, but can be degraded biologically by conversion into nontoxic compounds. Some bacteria are able to hydroxylate biphenyl and its polychlorinated biphenyls (PCBs). [2]

Biphenyl compounds

Substituted biphenyls can be prepared synthetically by various coupling reactions including the Suzuki reaction and the Ullmann reaction and have many uses. Polychlorinated biphenyls were once used as cooling and insulating fluids and polybrominated biphenyls are flame retardants. The biphenyl motif also appears in drugs such as Valsartan and Telmisartan. The abbreviation E7 stands for a liquid crystal mixture consisting of several cyanobiphenyls with long aliphatic tails used commercially in liquid crystal displays. A variety of benzidine derivatives are used in dyes and polymers. Research into Biphenyl liquid crystal candidates mainly focuses on molecules with highly polar heads (for example cyano or halide groups) and aliphatic tails.

References

  1. ^ Mikael P. Johansson and Jeppe Olsen (2008). "Torsional Barriers and Equilibrium Angle of Biphenyl: Reconciling Theory with Experiment". J. Chem. Theory Comput. 4: 1460. doi:10.1021/ct800182e. 
  2. ^ Biphenyl degradation - Streptomyces coelicolor, at GenomeNet Database
  • Biphenyl (1,1- Biphenyl). Wiley/VCH, Weinheim (1991), ISBN 3-527-28277-7

See also

External links








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