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106518

Sigma-Aldrich

Dodecahydrotriphenylene

99%

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About This Item

Empirical Formula (Hill Notation):
C18H24
CAS Number:
Molecular Weight:
240.38
Beilstein:
2051002
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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)
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)
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)
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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