1-Chloronaphthalene
{{chembox
| verifiedrevid = 477207437
| ImageFile=1-chloronaphthalene 200.svg
| ImageSize=150px
| PIN=1-Chloronaphthalene
| OtherNames=
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6737
| InChI = 1/C10H7Cl/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H
| InChIKey = JTPNRXUCIXHOKM-UHFFFAOYAV
| SMILES1 = c1ccc2c(c1)cccc2Cl
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 195338
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H7Cl/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JTPNRXUCIXHOKM-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=90-13-1
| PubChem=7003
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = K4OIF2EC56
| SMILES = Clc2cccc1ccccc12
}}
|Section2={{Chembox Properties
| C=10 | H=7 | Cl=1
| Appearance=
| Density=
| MeltingPtC= -20
| BoilingPtC= 263
| Solubility=
}}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}} {{GHS09}}
| GHSSignalWord = WARNING
| HPhrases = {{H-phrases|302|410}}
| PPhrases = {{P-phrases|273}}
| ExternalSDS = [http://msds.chem.ox.ac.uk/CH/1-chloronaphthalene.html Oxford MSDS]
| FlashPtC= 121
| AutoignitionPt =
}}
}}
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.{{Cite web |url=http://msds.chem.ox.ac.uk/CH/1-chloronaphthalene.html |title=Oxford MSDS |access-date=2008-12-21 |archive-date=2009-01-13 |archive-url=https://web.archive.org/web/20090113060651/http://msds.chem.ox.ac.uk/CH/1-chloronaphthalene.html |url-status=dead }} The compound is an isomer to 2-chloronaphthalene.
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.{{cite journal|last1=Bavendamm|first1=W.|last2=Bellmann|first2=H.|title=Chlornaphthalin-Präparate|journal=Holz Als Roh- und Werkstoff|date=1953|volume=11|issue=2 |pages=81–84|doi=10.1007/BF02605462|s2cid=138951084 |language=German}}
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{{cite web|title=1-Chloronaphthalene|url=http://www.sigmaaldrich.com/catalog/product/sial/25320?lang=en®ion=RU|website=Sigma Aldrich|publisher=sigmaaldrich.com|accessdate=14 June 2017}} for oils, fats and DDT until the 1970s. It is also used to determine the refractive index of crystals.