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Sigma-Aldrich

Dodecahydrotriphenylene

99%

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About This Item

Empirical Formula (Hill Notation):
C18H24
CAS Number:
1610-39-5
Molecular Weight:
240.38
Beilstein/REAXYS Number:
2051002
EC Number:
216-550-1
MDL number:
MFCD00001109
UNSPSC Code:
12352100
PubChem Substance ID:
24846736
NACRES:
NA.22

assay

99%

form

solid

mp

231-233 °C (lit.)

solubility

hexane: soluble

SMILES string

C1CCc2c(C1)c3CCCCc3c4CCCCc24

InChI

1S/C18H24/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H2

InChI key

ODHYDPYRIQKHCI-UHFFFAOYSA-N

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General description

Dodecahydrotriphenylene forms metal-carbonyl complexes. It undergoes hydrogenation and rearrangement by action of AlCl3 in inert atmosphere conditions at 20°C (hexane solution) or 70°C (heptane solution). It is formed by trimerization of cyclohexanone. It undergoes oxidation by peroxytrifluoroacetic acid and boron fluoride etherate at 0°C to form cross-conjugated cyclohexadieone.

Application

Dodecahydrotriphenylene was used to develop a set of new bacterial bioreporters and assays for detection of long chain alkanes based on the marine bacterium Alcanivorax borkumensis strain SK2.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Oxidations with peroxytrifluoracetic acid-boron fluoride. X. Oxidation of s-dodecahydrotriphenylene with peroxytrifluoracetic acid-boron fluoride and the photoisomerization of the resulting cyclohexadienones.
Hart H and Lankin DC.
The Journal of Organic Chemistry, 33(12), 4398-4402 (1968)
Hydrogenation and rearrangement of coal-related aromatic and hydroaromatic molecules promoted under mild conditions by aluminium trichloride.
Stobart SR and Zaworotko MJ.
Fuel: The Science and Technology of Fuel and Energy, 64(11), 1623-1624 (1985)
Metal-carbonyl complexes of dodecahydrotriphenylene; a comparison of the structures of iso-electronic [(η6C18H24) Mn (CO)3]+ and (η6C18H24) Cr (CO)3.
Gommans LHP, et al.
Journal of Organometallic Chemistry, 346(3), 385-395 (1988)
Rekha Kumari et al.
Environmental microbiology, 13(10), 2808-2819 (2011-09-08)
Long-chain alkanes are a major component of crude oil and therefore potentially good indicators of hydrocarbon spills. Here we present a set of new bacterial bioreporters and assays that allow to detect long-chain alkanes. These reporters are based on the

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