Tricyclodecane

Tricyclodecane (TCD) is an organic compound with the formula C₁₀H₁₆. It is classed as a hydrocarbon. It has two main stereoisomers–the endo and exo forms.^[2] Its primary use in the exo form is as a component of jet fuel.^[3] It is used here primarily because of its high energy density. The exo isomer also has a low freezing point.^[4][5] Because of this, its properties have been studied extensively.^{[6][7][8][9][10]} It is often called tetrahydrodicyclopentadiene.

Tricyclodecane

endo exo
Names
IUPAC name tricyclo[5.2.1.02,6]decane
Other names Tetrahydrodicyclopentadiene
Identifiers
CAS Number	6004-38-2
3D model (JSmol)	Interactive image
ChemSpider	16815
EC Number	227-851-2
PubChem CID	17795
CompTox Dashboard (EPA)	DTXSID60859773
InChI InChI=1S/C10H16/c1-2-9-7-4-5-8(6-7)10(9)3-1/h7-10H,1-6H2 Key: LPSXSORODABQKT-UHFFFAOYSA-N
SMILES C1CC2C3CCC(C3)C2C1
Properties
Chemical formula	C10H16
Molar mass	136.238 g·mol−1
Hazards
GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H226, H302, H304, H315, H319, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P330, P331, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, P501
Related compounds
Related compounds	Twistane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Reactions

Its reactions with other materials have been studied,^[11][12] as have various production methods.^[13][14] The two isomers can interconvert in the presence of aluminum chloride as catalyst absorbed on substrates such as silicon dioxide or zeolites,^{[15][16][17][18]} with preference for forming the exo as the major product.^[19][20]