Decalin (decahydronaphthalene, also known as bicyclo[4.4.0]decane and sometimes decaline),[3] a bicyclic organic compound, is an industrial solvent. A colorless liquid with an aromatic odor, it is used as a solvent for many resins or fuel additives.[4] It is the saturated analog of naphthalene and can be prepared from it by hydrogenation in the presence of a catalyst. Decalin easily forms explosive[5] organic peroxides upon storage in the presence of air.[6][7]

Preferred IUPAC name
Other names
3D model (JSmol)
ECHA InfoCard 100.001.861 Edit this at Wikidata
EC Number
  • 202-046-9, 207-770-9, 207-771-4
RTECS number
  • QJ3150000
UN number 1147
  • InChI=1S/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2 checkY
  • InChI=1/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2
  • cis: C1CC[C@H]2CCCC[C@H]2C1
  • trans: C1CC[C@H]2CCCC[C@@H]2C1
Molar mass 138.25 g/mol
Appearance colorless liquid
Density 0.896 g/cm3
Melting point trans: −30.4 °C (−22.7 °F, 242.7 K)
cis: −42.9 °C (−45.2 °F, 230.3 K)[2]
Boiling point trans: 187 °C (369 °F)
cis: 196 °C (384 °F)
  • −107.7·10−6 cm3/mol (trans)
  • −107.0·10−6 cm3/mol (cis)
Safety data sheet Decalin MSDS
GHS pictograms GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: HarmfulGHS08: Health hazardGHS09: Environmental hazard
GHS Signal word Danger
H226, H302, H305, H314, H318, H331, H332, H400, H410, H411
P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P273, P280, P301+310, P301+330+331, P303+361+353, P304+312, P304+340, P305+351+338, P310, P311, P312, P321, P331, P363, P370+378
Flash point 57 °C (135 °F; 330 K)
250 °C (482 °F; 523 K)
Related compounds
Related compounds
Naphthalene; Tetralin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references


Decahydronaphthalene occurs in cis and trans forms. The trans form is energetically more stable because of fewer steric interactions. cis-Decalin is a chiral molecule without a chiral center; it has a two-fold rotational symmetry axis, but no reflective symmetry. However, the chirality is canceled through a chair-flipping process that turns the molecule into its mirror image.


The only possible way to join the two six-membered rings in the trans position means the second ring needs to start from two equatorial bonds (blue) of the first ring. A six-membered ring does not offer sufficient space to start out on an axial position (upwards), and reach the axial position of the neighboring carbon atom, which then will be on the downwards side of the molecule (see the model of cyclohexane in figure 5). The structure is conformationally frozen, rather than having the ability to undergo the chair flip as in the cis isomer. In biology this fixation is widely used in the steroid skeleton to construct molecules (such as figure 6) that play a key role in the signalling between distantly separated cells.


Oxygenation of decalin give the tertiary hydroperoxide, which rearranges to cyclodecenone, a precursor to sebacic acid.[8]

See alsoEdit


  1. ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 33, 394, 601. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Haynes, William M. (2010). Handbook of Chemistry and Physics (91 ed.). Boca Raton, Florida, USA: CRC Press. p. 3-134. ISBN 978-1-43982077-3.
  3. ^ "".
  4. ^ "Fuel Additive Product". Archived from the original on 2009-03-12.
  5. ^ "PDF – Surrogate JP-8 Aviation Fuel Study – Alessandro Agosta Thesis Drexel University" (PDF). Archived from the original (PDF) on 2010-06-19.
  6. ^ " Data".
  7. ^ "MSDS Sheet – JT Baker".
  8. ^ Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227.