{{위키데이터 속성 추적}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477170210
| Name = 나프탈렌
| ImageFile = 
| ImageFileL1 = Naphthalene numbering.svg
| ImageSizeL1 = 100px
| ImageNameL1 = Skeletal formula and numbering system of naphthalene
| ImageFileR1 = Naphthalene-from-xtal-3D-balls.png
| ImageSizeR1 = 100px
| ImageNameR1 = Ball-and-stick model of naphthalene
| ImageFile2 = Naphthalene-from-xtal-3D-vdW.png
| ImageSize2 = 150px
| ImageName2 = Spacefill model of naphthalene
| ImageFile3 = Naphthalene-xtal-3D-vdW-B.png
| ImageSize3 = 150px
| ImageName3 = Unit cells of naphthalene
| PIN = Naphthalene<ref name=iupac2013>{{서적 인용| title =  Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The [[Royal Society of Chemistry]] | date = 2014 | location = Cambridge | pages = 13, 35, 204, 207, 221–222, 302, 457, 461, 469, 601, 650 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
| SystematicName = <!-- Von Baeyer nomenclature -->Bicyclo[4.4.0]deca-1,3,5,7,9-pentaene
| OtherNames = white tar, camphor tar, tar camphor, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes
| IUPACName = 
| Section1 = {{Chembox Identifiers
| CASNo = 91-20-3
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 931
| ChemSpiderID = 906
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = 2166IN72UN| ChEBI_Ref = {{ebicite|correct|EBI}}
| UNII_Ref = {{fdacite|changed|FDA}}
| EINECS = 214-552-7
| KEGG = C00829
| KEGG_Ref = {{keggcite|correct|kegg}}
| ChEBI = 16482
| ChEMBL = 16293
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = QJ0525000
| SMILES = c1=cc=c2c=cc=cc2=c1
| Beilstein = 1421310
| Gmelin = 3347
| InChI = 1/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
| InChIKey = UFWIBTONFRDIAS-UHFFFAOYAC
| StdInChI = 1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UFWIBTONFRDIAS-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
  }}
| Section2 = {{Chembox Properties
| C=10 | H=8
| Appearance = White solid crystals/ flakes
| Odor = Strong odor of coal tar
| Density = 1.145 g/cm<sup>3</sup> (15.5&nbsp;°C)<ref name=water.epa>{{웹 인용
|url = http://water.epa.gov/scitech/swguidance/standards/upload/2001_10_12_criteria_ambientwqc_napthalene80.pdf|title = Ambient Water Quality Criteria for Naphthalene|publisher = United States Environmental Protection Agency|accessdate = 2014-06-21|date = 2014-04-23}}</ref><br> 1.0253 g/cm<sup>3</sup> (20&nbsp;°C)<ref name=crc /><br> 0.9625 g/cm<sup>3</sup> (100&nbsp;°C)<ref name=water.epa />
| Solubility = 19 mg/L (10&nbsp;°C)<br> 31.6 mg/L (25&nbsp;°C)<br> 43.9 mg/L (34.5&nbsp;°C)<br> 80.9 mg/L (50&nbsp;°C)<ref name=crc /><br> 238.1 mg/L (73.4&nbsp;°C)<ref name=chemister>{{웹 인용|last = Anatolievich|first = Kiper Ruslan|website = chemister.ru|url = http://chemister.ru/Database/properties-en.php?dbid=1&id=1005|title = naphthalene|accessdate = 2014-06-21|archive-date = 2014-12-22|archive-url = https://web.archive.org/web/20141222130647/http://chemister.ru/Database/properties-en.php?dbid=1&id=1005|url-status = }}</ref>
| Solubility1 = 5 g/100 g (0&nbsp;°C)<br> 11.3 g/100 g (25&nbsp;°C)<br> 19.5 g/100 g (40&nbsp;°C)<br> 179 g/100 g (70&nbsp;°C)<ref name=sioc>{{서적 인용|last = Seidell|first = Atherton|last2 = Linke|first2 = William F.|year = 1919|title = Solubility of Inorganic and Organic Compounds|url = https://archive.org/details/solubilitiesino04seidgoog|publisher = D. Van Nostrand Company|place = New York|edition = 2nd|pages = [https://archive.org/details/solubilitiesino04seidgoog/page/n468 443]–446}}</ref>
| Solvent1 = 에탄올
| Solubility2 = 6.8 g/100 g (6.75&nbsp;°C)<br> 13.1 g/100 g (21.5&nbsp;°C)<br> 31.1 g/100 g (42.5&nbsp;°C)<br> 111 g/100 g (60&nbsp;°C)<ref name=sioc />
| Solvent2 = 아세트산
| Solubility3 = 19.5 g/100 g (0&nbsp;°C)<br> 35.5 g/100 g (25&nbsp;°C)<br> 49.5 g/100 g (40&nbsp;°C)<br> 87.2 g/100 g (70&nbsp;°C)<ref name=sioc />
| Solvent3 = 클로로포름
| Solubility4 = 5.5 g/100 g (0&nbsp;°C)<br> 17.5 g/100 g (25&nbsp;°C)<br> 30.8 g/100 g (40&nbsp;°C)<br> 78.8 g/100 g (70&nbsp;°C)<ref name=sioc />
| Solvent4 = 헥세인
| Solubility5 = 13.6 g/100 g (6.75&nbsp;°C)<br> 22.1 g/100 g (21.5&nbsp;°C)<br> 131.6 g/100 g (60&nbsp;°C)<ref name=sioc />
| Solvent5 = 뷰티르산
| SolubleOther = Soluble in [[알코올]], 액체 [[암모니아]], [[카복실산]], [[벤젠|C<sub>6</sub>H<sub>6</sub>]], [[이산화 황|SO<sub>2</sub>]],<ref name=chemister /> [[사염화 탄소|CCl<sub>4</sub>]], [[이황화 탄소|CS<sub>2</sub>]], [[톨루엔]], [[아닐린]]<ref name=sioc />
| MeltingPtC = 78.2
| MeltingPt_notes = <br> {{convert|80.26|C|F K}}<br> at 760 mmHg<ref name=crc />
| BoilingPtC = 217.97
| BoilingPt_notes = <br> at 760 mmHg<ref name=water.epa /><ref name=crc />
| VaporPressure = 8.64 Pa (20&nbsp;°C)<br> 23.6 Pa (30&nbsp;°C)<br> 0.93 kPa (80&nbsp;°C)<ref name=chemister /><br> 2.5 kPa (100&nbsp;°C)<ref name=nist>{{nist|name=Naphthalene|id=C91203|accessdate=2014-05-24|mask=FFFF|units=SI}}</ref>
| LogP = 3.34<ref name=crc />
| RefractIndex = 1.5898<ref name=crc />
| HenryConstant = 0.42438 L·atm/mol<ref name=crc />
| ThermalConductivity = 98 kPa:<br> 0.1219 W/m·K (372.22 K)<br> 0.1174 W/m·K (400.22 K)<br> 0.1152 W/m·K (418.37 K)<br> 0.1052 W/m·K (479.72 K)<ref>{{웹 인용 |title = Thermal Conductivity of Naphthalene |url = http://www.ddbst.com/en/EED/PCP/TCN_C123.php |website = DDBST GmbH |publisher = DDBST GmbH |accessdate = 2014-06-21 |archive-date = 2016-03-04 |archive-url = https://web.archive.org/web/20160304070707/http://www.ddbst.com/en/EED/PCP/TCN_C123.php |url-status =  }}</ref>
| Viscosity = 0.964 cP (80&nbsp;°C)<br> 0.761 cP (100&nbsp;°C)<br> 0.217 cP (150&nbsp;°C)<ref>{{웹 인용|title = Dynamic Viscosity of Naphthalene|url = http://www.ddbst.com/en/EED/PCP/VIS_C123.php|website = DDBST GmbH|publisher = DDBST GmbH|accessdate = 2014-06-21|archive-date = 2016-03-04|archive-url = https://web.archive.org/web/20160304104728/http://www.ddbst.com/en/EED/PCP/VIS_C123.php|url-status = }}</ref>
| MagSus = -91.9·10<sup>−6</sup> cm<sup>3</sup>/mol
  }}
| Section3 = {{Chembox Structure
| CrystalStruct = [[Monoclinic crystal system|Monoclinic]]<ref name=sccs>{{서적 인용|url = https://books.google.com/books?id=hYRCAAAAQBAJ&pg=PA288|title = Structure and Chemistry of Crystalline Solids|last = Douglas|first = Bodie E.|last2 = Ho|first2 = Shih-Ming|publisher = Springer Science+Business Media, Inc.|year = 2007|isbn = 978-0-387-26147-8|place = New York|page = 288}}</ref>
| SpaceGroup = P2<sub>1</sub>/b<ref name=sccs />
| PointGroup = C{{sup sub|5|2h}}<ref name=sccs />
| LattConst_a = 8.235&nbsp;Å
| LattConst_b = 6.003&nbsp;Å
| LattConst_c = 8.658&nbsp;Å<ref name=sccs />
| LattConst_alpha =
| LattConst_beta = 122.92
| LattConst_gamma =
  }}
| Section4 = {{Chembox Thermochemistry
| HeatCapacity = 165.72 J/mol·K<ref name=crc />
| Entropy = 167.39 J/mol·K<ref name=crc /><ref name=nist />
| DeltaHf = 78.53 kJ/mol<ref name=crc />
| DeltaGf = 201.585 kJ/mol<ref name=crc />
| DeltaHc = -5156.3 kJ/mol<ref name=crc />
  }}
| Section5 = 
| Section6 = 
| Section7 = {{Chembox Hazards
| MainHazards = [[Combustibility and flammability|Flammable]], [[wikt:sensitizer|sensitizer]], possible [[carcinogen]]. Dust can form [[explosive]] mixtures with [[Atmosphere of Earth|air]]
| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}{{GHS09}}<ref name="sigma">{{Sigma-Aldrich|id=147141|name=Naphthalene|accessdate=2014-06-21}}</ref>
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|228|302|351|410}}<ref name="sigma" />
| PPhrases = {{P-phrases|210|273|281|501}}<ref name="sigma" />
| NFPA-H = 2
| NFPA-F = 2
| NFPA-R = 0
| FlashPtC = 80
| FlashPt_ref =<ref name="sigma" />
| AutoignitionPtC = 525
| AutoignitionPt_ref =<ref name="sigma" />
| ExploLimits = 5.9%<ref name="sigma" />
| TLV-TWA = 10 ppm<ref name=crc>{{CRC90}}</ref>
| TLV-STEL = 15 ppm<ref name=crc />
| LD50 = 1800 mg/kg (rat, oral)<br/>490 mg/kg (rat, oral)<br/>1200 mg/kg (guinea pig, oral)<br/>533 mg/kg (mouse, oral)<ref>{{IDLH|91203|Naphthalene}}</ref>
| IDLH = 250 ppm<ref name=PGCH>{{PGCH|0439}}</ref>
| REL = TWA 10 ppm (50 mg/m<sup>3</sup>) ST 15 ppm (75 mg/m<sup>3</sup>)<ref name=PGCH/>
| PEL = TWA 10 ppm (50 mg/m<sup>3</sup>)<ref name=PGCH/>
  }}
}}
'''나프탈렌'''({{llang|en|naphthalene}})은 [[벤젠]]고리가 2개 있는 [[방향족]] [[탄화수소]]로 [[승화 (화학)|승화]]성이 있다. 비늘 모양의 백색 결정으로 분자량은 128, 녹는점은 80.3&nbsp;°C, 끓는점은 217.97&nbsp;°C이며, 비중은 0.975(25&nbsp;°C)이다. 분자식은 [[탄소|C]]<sub>10</sub>[[수소|H]]<sub>8</sub>로 쓴다. [[물]]에는 녹지 않고, [[에탄올]]에는 녹는다.
일반적으로 재래식 [[화장실]]에서 파리 등 유해한 벌레를 쫓는 방충제 또는 살충제의 성분으로 쓰인다.

== 건강에 미치는 영향 ==
나프탈렌에 많이 노출되면 간이 손상된다. 인간, 특히 어린이가 나프탈렌 또는 나프탈렌이 함유된 탈취제 블럭을 삼킬 경우 용혈성 빈혈이 나타난다. 적은 양에도 오래 노출되면 어지러움, 구토, 혈뇨, 황달 등 증세가 나타날 수 있으며 어떤 사람들에게는 더 위험하다고 알려져 있다.

캘리포니아 제안- 65에 따라, 나프탈렌은 "암을 유발하는 상태로 알려진"으로 표시된다. 좀약을 비롯하여 나프탈렌을 포함하는 탈취제에서 암을 일으킬 수 있는 메커니즘이 발견되었다

나프탈렌에 다량 노출되면 구토 및 어지러움 증상을 유발할 수 있으므로 주의해야 한다.

== 같이 보기 ==
* [[장뇌]]
== 각주 ==
{{각주}}

== 외부 링크 ==
* {{위키공용분류-줄}}

{{탄화수소}}
{{전거 통제}}

[[분류:나프탈렌| ]]
[[분류:여러 고리 방향족 탄화수소]]
[[분류:IARC 2B군 발암 물질]]