Decalin

Names
Preferred IUPAC name

Decahydronaphthalene[1]

Other names

Bicyclo[4.4.0]decane[1]
Decalin

Identifiers

CAS Number

* 91-17-8 Y

3D model (JSmol)

* Interactive image
* cis: Interactive image
* trans: Interactive image

Beilstein Reference

| 878165
ChEBI |

* CHEBI:38853 Y
* cis: CHEBI:38860
* trans: CHEBI:38863

ChEMBL |

* ChEMBL1491920

ChemSpider |

* 6777 Y

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

InChI

* InChI=1S/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2 Y

Key: NNBZCPXTIHJBJL-UHFFFAOYSA-N Y

* 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 | 138.25 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)

Solubility in water

| Insoluble

Magnetic susceptibility (χ)

* −107.7·10−6 cm3/mol (trans)
* −107.0·10−6 cm3/mol (cis)

Refractive index (nD)

| 1.481
Hazards
Safety data sheet | Decalin MSDS
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H226, H302, H305, H314, H331, H332, H410, H411

GHS precautionary statements

| 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)

Autoignition
temperature

|  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).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

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]

## Contents

* 1 Isomers
* 1.1 trans-Decalin
* 2 Reactions
* 3 Occurrence
* 4 Safety
* 5 See also
* 6 References

## Isomers

Decalin 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.

* 1: trans (left) and cis (right) isomers

* 2:

ball-and-stick model of cis-decalin

* 3:

trans-decalin

* 4:

cis-decalin ring-flip

### trans-Decalin

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. It does not have the ability to undergo a 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.

## Reactions

Oxygenation of decalin gives the tertiary hydroperoxide, which rearranges to cyclodecenone, a precursor to sebacic acid.[5]

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.[6]

## Occurrence

Decalin itself is rare in nature but several decalin derivatives are known. They arise via terpene-derived precursors or polyketides.[7]

## Safety

Decalin easily forms explosive[8] hydroperoxides upon storage in the presence of air.[9][10]

## See also

* Perfluorodecalin
* Tetralin
* Dialin
* Naphthalene

## References

1. ↑ 1.0 1.1 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: CRC Press. p. 3-134. ISBN 978-1439820773.
3. ↑ "Dictionary.com". http://dictionary.reference.com/browse/decahydronaphthalene.
4. ↑ "Fuel Additive Product". http://www.decalinchemicals.com/fueladditive.html.
5. ↑ Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter et al. (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227.
6. ↑ 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. doi:10.1016/j.rser.2017.04.006.
7. ↑ 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.
8. ↑ "PDF – Surrogate JP-8 Aviation Fuel Study – Alessandro Agosta Thesis Drexel University". http://idea.library.drexel.edu/bitstream/1860/16/11/agosta_thesis.pdf.
9. ↑ "Inchem.org Data". http://www.inchem.org/documents/icsc/icsc/eics1548.htm.
10. ↑ "MSDS Sheet – JT Baker". http://hazard.com/msds/mf/baker/baker/files/d0064.htm.

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*[CID]: Compound ID
*[H226]: Flammable liquid and vapour
*[H302]: Harmful if swallowed
*[H305]: May be harmful if swallowed and enters airways
*[H314]: Causes severe skin burns and eye damage
*[H331]: Toxic if inhaled
*[H332]: Harmful if inhaled
*[H410]: Very toxic to aquatic life with long lasting effects
*[H411]: Toxic to aquatic life with long lasting effects
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+310]: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+312]: IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P311]: Call a POISON CENTER or doctor/physician
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P331]: Do NOT induce vomiting
*[P363]: Wash contaminated clothing before reuse
*[P370+378]: In case of fire: Use … for extinction