1610-39-5

Basic information

• Product Name: Dodecahydrotriphenylene
• Synonyms: DODECAHYDROTRI-O-PHENYLENE;DODECAHYDROTRIPHENYLENE;1,2,3,4,5,6,7,8,9,10,11,12-Dodecahydrotriphenylene;triphenylene,1,2,3,4,5,6,7,8,9,10,11,12-dodecahydro-;Tritetralin;DODECAHYDROTRIPHENYLENE OEKANAL 250 MG;Dodecahydrotriphenylene,99%;200000.000 KG
• CAS NO: 1610-39-5
• Molecular Formula: C₁₈H₂₄
• Molecular Weight: 240.38
• EINECS: 216-550-1
• Product Categories: Miscellaneous;Arenes;Building Blocks;Organic Building Blocks
• Mol File: 1610-39-5.mol
• Article Data: 27

Chemical Properties

• Melting Point: 231-233 °C(lit.)
• Boiling Point: 318.11°C (rough estimate)
• Flash Point: 174.3 °C
• Appearance: white to yellow-beige fine crystalline powder
• Density: 0.9356 (estimate)
• Vapor Pressure: 3.82E-05mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Solubility: hexane: soluble
• BRN: 2051002
• CAS DataBase Reference: Dodecahydrotriphenylene(CAS DataBase Reference)
• NIST Chemistry Reference: Dodecahydrotriphenylene(1610-39-5)
• EPA Substance Registry System: Dodecahydrotriphenylene(1610-39-5)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 1610-39-5(Hazardous Substances Data)

Usage

Description

Dodecahydrotriphenylene is a white to yellow-beige fine crystalline powder that forms metal-carbonyl complexes. It is synthesized by the trimerization of cyclohexanone and can undergo hydrogenation and rearrangement through the action of AlCl3 in inert atmosphere conditions. Additionally, it can be oxidized by peroxytrifluoroacetic acid and boron fluoride etherate at 0°C to form cross-conjugated cyclohexadieone.

Uses

Used in Environmental Applications:
Dodecahydrotriphenylene is used as a component in the development of bacterial bioreporters and assays for the detection of long-chain alkanes. This application is particularly focused on utilizing the marine bacterium Alcanivorax borkumensis strain SK2 for environmental monitoring and assessment of hydrocarbon pollution.
Used in Chemical Research:
As a compound that forms metal-carbonyl complexes and undergoes various chemical reactions, Dodecahydrotriphenylene is used as a research compound in the field of organic chemistry. Its ability to participate in hydrogenation, rearrangement, and oxidation reactions makes it a valuable substance for studying chemical properties and reactions involving similar compounds.
Used in Industrial Applications:
Dodecahydrotriphenylene's formation through the trimerization of cyclohexanone and its involvement in metal-carbonyl complex formation make it a potential candidate for use in various industrial applications, such as the production of specialty chemicals, materials, or catalysts that require specific structural or functional properties.

InChI:InChI=1/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

Upstream product

• 1079-71-6 1,2,3,4,5,6,7,8-octahydroanthracene 
• 5325-97-3 1,2,3,4,5,6,7,8-Octahydrophenanthrene 
• 101886-56-0 2'-cyclohex-1-enyl-bicyclohexyliden-2-one 
• 108-94-1 cyclohexanone 
• 872-53-7 cyclopentanealdehyde 
• 7664-93-9 sulfuric acid 
• 217-59-4 triphenylene 
• 52897-78-6 13,15,17-Trihydroxyperhydrotriphenylen 
• 1589-69-1 1,2-cyclohex-1-enylene 
• 17975-64-3 4-cyclopentylidene-3-methylisoxazol-5(4H)-one 
• 51-79-6 urethane 
• 110-56-5 1,4-dichlorobutane 
• 71-43-2 benzene 
• 4844-47-7 Trispiro<4.1,4.1,4.1>octadecan-6,12,18-triol 

Downstream Products

• 217-59-4 triphenylene 
• 5981-10-2 1,2,3,4-tetrahydrotriphenylene 
• 517-60-2 benzenehexacarboxylic acid 
• 68558-73-6 triphenyleno<1,12-bcd>thiophene 
• 124-04-9 Adipic acid 

Related news

Conformational inversion in the Dodecahydrotriphenylene (cas 1610-39-5) radical cation07/21/2019

The temperature dependence of the e.s.r. spectrum of the radical cation of dodecahydrotriphenylene (2∔) shows that the activation energy for inversion of the (benzo)cyclohexene ring is 4.8 kcal mol-1, less than it is in the octahydroanthracene radical cation (1∔).detailed

Relevant articles and documents

The Direct Production of Tri- and Hexa-Substituted Benzenes from Ketones under Mild Conditions

Treatment of aryl methyl ketones with tetrachlorosilane in ethanol gives good yields of 1,3,5-triarylbenzenes.Triannulated benzenes result from cyclopentanone and cyclohexanone.

Synthesis of 1,4,5,8,9,12-hexabromododecahydrotriphenylene and its application in constructing polycyclic thioaromatics

A new route for constructing PAHs from cyclohexanone by trimerization, bromination, trisannulation and aromatization, and the synthesis of a novel sulfur-containing polycyclic heteroaromatic have been described. The Royal Society of Chemistry 2009.

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Trisannelated Benzene Synthesis by Zirconium Halide Catalysed Cyclodehydration of Cycloalkanones

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A new method for the preparation of 1,3,5-triarylbenzenes catalyzed by nanoclinoptilolite/HDTMA

A new natural surface modified nanoclinoptilolite (NCP) was prepared and applied as an efficient catalyst for the cyclotrimerization of acetophenones to obtain 1,3,5-triarylbenzenes. The results showed that the efficiency of this catalytic system was enhanced due to the surface modification by hexadecyltrimethylammonium bromide (HDTMA-Br). This proposed protocol brings about significant economic and environmental advantages, such as operational simplicity, short reaction time, mild reaction conditions, good reaction yield, and high recyclability of the catalyst. Furthermore, the only side product of the reaction is water, which makes this methodology an environmentally friendly process.

Selective catalytic hydrogenation of polycyclic aromatic hydrocarbons promoted by ruthenium nanoparticles

Ru nanoparticles stabilised by PPh3 are efficient catalysts for hydrogenation of polycyclic aromatic hydrocarbons (PAHs) containing 2-4 rings under mild reaction conditions. These compounds were partially hydrogenated with good to excellent selectivities just by optimizing the reaction conditions. The influence of the nature of substituents present in different positions of naphthalene on the selectivity of hydrogenation was also studied. Hydrogenation of products containing substituents at position 1 is slower than that of products containing substituents at position 2. In all cases, hydrogenation takes place mainly on the less substituted ring.