Decalin

Decalin
	Decalin
Names
	Preferred IUPAC name Decahydronaphthalene
	Other names Bicyclo[4.4.0]decane
Identifiers
CAS Number	91-17-8 ;
3D model (JSmol)	Interactive image; cis: Interactive image; trans: Interactive image;
Beilstein Reference	878165
ChEBI	CHEBI:38853 ; cis: CHEBI:38860; trans: CHEBI:38863;
ChEMBL	ChEMBL1491920;
ChemSpider	6777 ;
ECHA InfoCard	100.001.861
EC Number	202-046-9, 207-770-9, 207-771-4;
Gmelin Reference	185147
PubChem CID	7044;
RTECS number	QJ3150000;
UNII	88451Q4XYF;
UN number	1147
CompTox Dashboard (EPA)	DTXSID1024912 ;
	InChI InChI=1S/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2 Key: NNBZCPXTIHJBJL-UHFFFAOYSA-N ; InChI=1/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2 Key: NNBZCPXTIHJBJL-UHFFFAOYAH;
	SMILES C1CCC2CCCCC2C1; cis: C1CC[C@H]2CCCC[C@H]2C1; trans: C1CC[C@H]2CCCC[C@@H]2C1;
Properties
Chemical formula	C10H18
Molar mass	138.254 g·mol−1
Appearance	colorless liquid
Odor	slight, resembling menthol
Density	cis: 0.8965 g/cm3; trans: 0.8659 g/cm3;
Melting point	cis: −42.9 °C (−45.2 °F; 230.2 K); trans: −30.4 °C (−22.7 °F; 242.8 K);
Boiling point	cis: 195.8 °C (384.4 °F; 468.9 K); trans: 187.3 °C (369.1 °F; 460.4 K);
Solubility in water	Insoluble
Solubility in Ethanol	cis: Miscible; trans: Very soluble;
Solubility in Diethyl ether	Very soluble
Solubility in Acetone	Very soluble
Solubility in Chloroform	cis: Very soluble
Solubility in Benzene	trans: Miscible
Solubility in Methanol	trans: Soluble
log P	4.79
Vapor pressure	1.3 mbar (1.3 hPa) (22 °C (72 °F; 295 K)); 42 mmHg (5.6 kPa) (92 °C (198 °F; 365 K)); 741 mmHg (98.8 kPa) (188 °C (370 °F; 461 K));
Magnetic susceptibility (χ)	cis: −107.0×10−6 cm3/mol; trans: −107.7×10−6 cm3/mol[citation needed];
Refractive index (nD)	cis: 1.4810; trans: 1.4695;
Viscosity	3 mPa·s (20 °C (68 °F; 293 K))
Structure
Point group	cis: C2; trans: C2h;
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H304, H314, H331, H410
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340+P310, P305+P351+P338+P310, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)	3 2 1
Flash point	57 °C (135 °F; 330 K)
Autoignition; temperature	250 °C (482 °F; 523 K)
Explosive limits	0.7%–4.9% (100 °F (38 °C; 311 K))
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	4170 mg/kg (oral, rat); 5200 mg/kg (dermal, rabbit);
LC50 (median concentration)	4.08 mg/L (inhalation, rat)
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). verify (what is ?) Infobox references

Decalin (decahydronaphthalene, also known as bicyclo[4.4.0]decane and sometimes decaline), 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.^[6]

Isomers

Decalin occurs in cis and trans forms. The trans form is energetically more stable because of fewer steric effects. 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.^{[citation needed]}

1: trans (left) and cis (right) isomers
2:
ball-and-stick model of cis-decalin
3:
trans-decalin
4:
cis-decalin ring-flip

Synthesis

Decalin is the saturated analog of naphthalene and can be prepared from it by hydrogenation in the presence of a catalyst. This interconversion has been considered in the context of hydrogen storage.^[7]

Occurrence

Decalin itself is rare in nature but several decalin derivatives are known. They arise via terpene-derived precursors or polyketides.^[8]

Reactions

Oxygenation of decalin gives the tertiary hydroperoxide, which rearranges via hydroxycyclodecanone to cyclodecenone, a precursor to sebacic acid.^[9]

Safety

Decalin easily forms explosive hydroperoxides upon storage in the presence of air.^[10]^[11]

References

1 2 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: Royal Society of Chemistry. 2014. pp. 33, 394, 601. ISBN 978-0-85404-182-4.
↑ Lide, David R., ed. (2004). CRC Handbook of Chemistry and Physics (85th ed.). Boca Raton, FL: CRC Press. p. 3—148. ISBN 978-0-8493-0485-9.
1 2 3 4 "SDS - Decahydronapthalene" (pdf). thermofisher.com. ThermoFisher Scientific. 21 December 2025. p. 4. Retrieved 26 January 2026.
1 2 3 4 5 6 7 Sigma-Aldrich Co., Decahydronapthalene (cis, trans).
↑ Eliel, Ernest Ludwig; Wilen, Samuel H.; Mander, Lewis N. (1994). Stereochemistry of Organic Compounds. New York: Wiley. p. 777. ISBN 978-0-471-01670-0.
↑ "Fuel Additive Product". Archived from the original on 2009-03-12.
↑ Isa, Khairuddin Md; Abdullah, Tuan Amran Tuan; Ali, Umi Fazara Md (2018). "Hydrogen donor solvents in liquefaction of biomass: A review". Renewable and Sustainable Energy Reviews. 81: 1259–1268. Bibcode:2018RSERv..81.1259I. doi:10.1016/j.rser.2017.04.006.
↑ Li, Gang; Kusari, Souvik; Spiteller, Michael (2014). "Natural products containing 'decalin' motif in microorganisms". Nat. Prod. Rep. 31 (9): 1175–1201. doi:10.1039/C4NP00031E. PMID 24984916.
↑ Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227. ISBN 978-3-527-30673-2.
↑ Agosta, Alessandro (May 2002). Development of a Chemical Surrogate for JP-8 Aviation Fuel Using a Pressurized Flow Reactor (PDF) (MS thesis). Philadelphia, PA: Drexel University. Archived from the original (PDF) on 2010-06-19.
↑ International Chemical Safety Card 1548

[iupac2013-1] 1 2 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: Royal Society of Chemistry. 2014. pp. 33, 394, 601. ISBN 978-0-85404-182-4.

[CRC85-2] Lide, David R., ed. (2004). CRC Handbook of Chemistry and Physics (85th ed.). Boca Raton, FL: CRC Press. p. 3—148. ISBN 978-0-8493-0485-9.

[FisherSDS-3] 1 2 3 4 "SDS - Decahydronapthalene" (pdf). thermofisher.com. ThermoFisher Scientific. 21 December 2025. p. 4. Retrieved 26 January 2026.

[Sigma-4] 1 2 3 4 5 6 7 Sigma-Aldrich Co., Decahydronapthalene (cis, trans).

[Eliel1994-5] Eliel, Ernest Ludwig; Wilen, Samuel H.; Mander, Lewis N. (1994). Stereochemistry of Organic Compounds. New York: Wiley. p. 777. ISBN 978-0-471-01670-0.

[6] "Fuel Additive Product". Archived from the original on 2009-03-12.

[7] Isa, Khairuddin Md; Abdullah, Tuan Amran Tuan; Ali, Umi Fazara Md (2018). "Hydrogen donor solvents in liquefaction of biomass: A review". Renewable and Sustainable Energy Reviews. 81: 1259–1268. Bibcode:2018RSERv..81.1259I. doi:10.1016/j.rser.2017.04.006.

[8] Li, Gang; Kusari, Souvik; Spiteller, Michael (2014). "Natural products containing 'decalin' motif in microorganisms". Nat. Prod. Rep. 31 (9): 1175–1201. doi:10.1039/C4NP00031E. PMID 24984916.

[Ull-9] Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227. ISBN 978-3-527-30673-2.

[10] Agosta, Alessandro (May 2002). Development of a Chemical Surrogate for JP-8 Aviation Fuel Using a Pressurized Flow Reactor (PDF) (MS thesis). Philadelphia, PA: Drexel University. Archived from the original (PDF) on 2010-06-19.

[11] International Chemical Safety Card 1548

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

This page was redesigned at the edge.