1-Chloronaphthalene

1-Chloronaphthalene is an aromatic compound. It is a colorless, oily liquid which may be used to determine the refractive index of crystals by immersion.[1] The compound is an isomer to 2-chloronaphthalene.

1-Chloronaphthalene
Names
Preferred IUPAC name
1-Chloronaphthalene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.789
UNII
  • InChI=1S/C10H7Cl/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H checkY
    Key: JTPNRXUCIXHOKM-UHFFFAOYSA-N checkY
  • InChI=1/C10H7Cl/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H
    Key: JTPNRXUCIXHOKM-UHFFFAOYAV
  • Clc2cccc1ccccc12
  • c1ccc2c(c1)cccc2Cl
Properties
C10H7Cl
Molar mass 162.62 g·mol−1
Melting point −20 °C (−4 °F; 253 K)
Boiling point 263 °C (505 °F; 536 K)
Hazards
GHS labelling:
GHS07: Exclamation mark GHS09: Environmental hazard
Warning
H302, H410
P273
Flash point 121 °C (250 °F; 394 K)
Safety data sheet (SDS) Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Synthesis

1-Chloronaphthalene is obtained directly by chlorination of naphthalene, with the formation of more highly substituted derivatives such as dichloro- and trichloronaphthalenes in addition to the two monochlorinated isomeric compounds: 1-chloronaphthalene and 2-chloronaphthalene.[2]

Applications

This toxic, nonpolar organochlorine compound is sometimes used as a powerful biocide, and is also known as Basileum. It occasionally serves as insecticide and fungicide in the timber floors of shipping containers, where it fulfills the same role as chlordane.

1-Chloronaphthalene was also used as a common solvent[3] for oils, fats and DDT until the 1970s. It is also used to determine the refractive index of crystals.

See also

References
  1. "Oxford MSDS". Archived from the original on 2009-01-13. Retrieved 2008-12-21.
  2. Bavendamm, W.; Bellmann, H. (1953). "Chlornaphthalin-Präparate". Holz Als Roh- und Werkstoff (in German). 11 (2): 81–84. doi:10.1007/BF02605462. S2CID 138951084.
  3. "1-Chloronaphthalene". Sigma Aldrich. sigmaaldrich.com. Retrieved 14 June 2017.
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