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Perhydrophenanthrene, also known as emelentane or tricyclo[9.1.0.04,7]decane, is a chemical compound that is a polycyclic alkane derivative of phenanthrene. It has a molecular formula of C14H20 and falls under the structural classification of polycyclic hydrocarbons. With a molar mass of around 188.31 g/mol, this chemical is predominantly used in research and development (R&D) settings, particularly for studies involving biological and chemical interactions. Its physical and chemical properties, such as melting and boiling points, are not extensively documented, likely due to its rarity and R&D-focused applications.

5743-97-5

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5743-97-5 Usage

Uses

Used in Research and Development:
Perhydrophenanthrene is used as a research compound for studying biological and chemical interactions. Its unique structure and properties make it a valuable tool in various scientific investigations.
Used in Chemical Synthesis:
In the field of organic chemistry, perhydrophenanthrene is used as an intermediate or a building block in the synthesis of more complex molecules. Its polycyclic structure provides a foundation for creating a wide range of chemical compounds.
Used in Material Science:
Perhydrophenanthrene may also find applications in material science, where its unique properties could be utilized in the development of new materials with specific characteristics, such as improved stability or enhanced reactivity.
Used in Pharmaceutical Research:
In the pharmaceutical industry, perhydrophenanthrene could be used as a starting material for the development of new drugs or as a model compound to study the interactions between molecules and biological targets. Its potential applications in drug discovery make it an important compound in medicinal chemistry research.

Check Digit Verification of cas no

The CAS Registry Mumber 5743-97-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,7,4 and 3 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 5743-97:
(6*5)+(5*7)+(4*4)+(3*3)+(2*9)+(1*7)=115
115 % 10 = 5
So 5743-97-5 is a valid CAS Registry Number.
InChI:InChI=1/C14H24/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h11-14H,1-10H2

5743-97-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Tetradecahydrophenanthrene

1.2 Other means of identification

Product number -
Other names Phenanthrene, tetradecahydro-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5743-97-5 SDS

5743-97-5Synthetic route

phenanthrene
85-01-8

phenanthrene

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
With kieselguhr; nickel at 225℃;
With phosphorus; hydrogen iodide at 250 - 260℃;
With nickel(II) oxide; hydrogen at 320 - 370℃;
1,2,3,4,5,6,7,8-Octahydrophenanthrene
5325-97-3

1,2,3,4,5,6,7,8-Octahydrophenanthrene

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
With nickel at 160℃; under 55163.1 Torr; Hydrogenation; isomer(ic) of doubtful homogeneity;
(4aR,8aS,9aR,10aS)-tetradecahydroanthracene
1755-19-7

(4aR,8aS,9aR,10aS)-tetradecahydroanthracene

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
With aluminium trichloride Erhitzen auf dem Dampfbad; isomer(ic) of doubtful homogeneity;
With molybdenum (IV) sulfide; hydrogen at 460℃; under 73550.8 Torr; isomer(ic) of doubtful homogeneity;
phenanthrene
85-01-8

phenanthrene

A

1,2,3,4,4a,9,10,10a-octahydrophenanthrene
16306-39-1

1,2,3,4,4a,9,10,10a-octahydrophenanthrene

B

9,10-dihydrophenanthrene
776-35-2

9,10-dihydrophenanthrene

C

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
With hydrogen; iron In decalin at 350℃; under 73550.8 Torr; Product distribution; hydrogenation with other iron catalyst;
Δ4b(8a)-dodecahydrophenanthrene

Δ4b(8a)-dodecahydrophenanthrene

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
With nickel at 240℃; under 147102 Torr; Hydrogenation; isomer(ic) of doubtful homogeneity;
With nickel; methyl cyclohexane at 250℃; under 77228.3 - 102971 Torr; Hydrogenation; isomer(ic) of doubtful homogeneity;
phenanthrene
85-01-8

phenanthrene

sulfuric acid
7664-93-9

sulfuric acid

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
bei der Elektrolyse an einer palladinierten Platinkathode;
7-hydroxy-9-oxo-1.2.3.4.4a.9.10.10a-octahydro-phenanthrene

7-hydroxy-9-oxo-1.2.3.4.4a.9.10.10a-octahydro-phenanthrene

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
With acetic acid; platinum Hydrogenation; isomer(ic) of doubtful homogeneity;
9-hydroxy-1.2.3.4.4a.9.10.10a-octahydro-phenanthrene

9-hydroxy-1.2.3.4.4a.9.10.10a-octahydro-phenanthrene

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
With ethanol; acetic acid; platinum Hydrogenation; isomer(ic) of doubtful homogeneity;
9-oxo-tetradecahydrophenanthrene

9-oxo-tetradecahydrophenanthrene

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
With hydrogenchloride; amalgamated zinc; acetic acid isomer of mp: 10 degree;
ethanol
64-17-5

ethanol

phenanthrene
85-01-8

phenanthrene

ammonia
7664-41-7

ammonia

calcium

calcium

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

phenanthrene
85-01-8

phenanthrene

methyl cyclohexane
82166-21-0

methyl cyclohexane

copper chromite

copper chromite

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
at 300℃; under 110326 - 147102 Torr; Hydrogenation;
1,2,3,4,5,6,7,8-Octahydrophenanthrene
5325-97-3

1,2,3,4,5,6,7,8-Octahydrophenanthrene

nickel

nickel

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
at 160℃; under 55163.1 Torr; Hydrogenation;
phenanthrene
85-01-8

phenanthrene

water
7732-18-5

water

aluminium

aluminium

palladium

palladium

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

cyclohexane
110-82-7

cyclohexane

phenanthrene
85-01-8

phenanthrene

hydrogen

hydrogen

palladium

palladium

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

phenanthrene
85-01-8

phenanthrene

NaH2PO2

NaH2PO2

palladium

palladium

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

diethyl ether
60-29-7

diethyl ether

phenanthrene
85-01-8

phenanthrene

hydrogen

hydrogen

platinum black

platinum black

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

phenanthrene
85-01-8

phenanthrene

methyl cyclohexane
82166-21-0

methyl cyclohexane

Raney nickel

Raney nickel

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
at 250℃; under 73550.8 - 147102 Torr; Hydrogenation;
phenanthrene
85-01-8

phenanthrene

ammonia
7664-41-7

ammonia

sodium ammonium

sodium ammonium

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

hydrogenchloride
7647-01-0

hydrogenchloride

phenanthrene
85-01-8

phenanthrene

zinc

zinc

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

9,10-dihydrophenanthrene
776-35-2

9,10-dihydrophenanthrene

Raney nickel

Raney nickel

A

phenanthrene
85-01-8

phenanthrene

B

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

C

1,2,3,4-tetrahydrophenanthrene
1013-08-7

1,2,3,4-tetrahydrophenanthrene

Conditions
ConditionsYield
at 250℃; under 73550.8 - 102971 Torr;
phenanthrene
85-01-8

phenanthrene

MoS2

MoS2

A

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

B

1,2,3,4,5,6,7,8-Octahydrophenanthrene
5325-97-3

1,2,3,4,5,6,7,8-Octahydrophenanthrene

C

1.2.3.4-tetrahydro-phenanthrene(?)

1.2.3.4-tetrahydro-phenanthrene(?)

Conditions
ConditionsYield
at 330 - 370℃; under 73550.8 Torr; Hydrogenation;
phenanthrene
85-01-8

phenanthrene

methyl cyclohexane
82166-21-0

methyl cyclohexane

Raney nickel

Raney nickel

A

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

B

1,2,3,4,5,6,7,8-Octahydrophenanthrene
5325-97-3

1,2,3,4,5,6,7,8-Octahydrophenanthrene

C

Δ4b(8a)-dodecahydro-phenanthrene(?)

Δ4b(8a)-dodecahydro-phenanthrene(?)

D

cis(?)-1.2.3.4.4a.9.10.10a-octahydro-phenanthrene

cis(?)-1.2.3.4.4a.9.10.10a-octahydro-phenanthrene

Conditions
ConditionsYield
at 200℃; under 147102 - 220652 Torr; Hydrogenation;
(+/-)-7-hydroxy-(4arH.10acH)-1.2.3.4.4a.9.10.10a-octahydro-phenanthrene
82381-07-5

(+/-)-7-hydroxy-(4arH.10acH)-1.2.3.4.4a.9.10.10a-octahydro-phenanthrene

acetic acid
64-19-7

acetic acid

platinum

platinum

A

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

B

2ξ-hydroxy-(4aξH.4brH.8acH.10aξH)-tetradecahydro-phenanthrene

2ξ-hydroxy-(4aξH.4brH.8acH.10aξH)-tetradecahydro-phenanthrene

Conditions
ConditionsYield
Hydrogenation;
7-hydroxy-cis-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one

7-hydroxy-cis-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one

acetic acid
64-19-7

acetic acid

platinum

platinum

A

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

B

(4aξH.4brH.8acH.10aξH)-tetradecahydro-phenanthrenediol-(2ξ.10ξ)

(4aξH.4brH.8acH.10aξH)-tetradecahydro-phenanthrenediol-(2ξ.10ξ)

C

(4arH.10acH)-1.2.3.4.4a.9.10.10a-octahydro-phenanthrol-(7)

(4arH.10acH)-1.2.3.4.4a.9.10.10a-octahydro-phenanthrol-(7)

D

(4aξH.4brH.8acH.10aξH)-tetradecahydro-phenanthrol-(2ξ)

(4aξH.4brH.8acH.10aξH)-tetradecahydro-phenanthrol-(2ξ)

Conditions
ConditionsYield
Hydrogenation;
ethanol
64-17-5

ethanol

1,2,3,4,4a,9,10,10a-Octahydro-phenanthrol-(9)
25662-65-1, 28352-26-3, 74897-71-5

1,2,3,4,4a,9,10,10a-Octahydro-phenanthrol-(9)

acetic acid
64-19-7

acetic acid

platinum

platinum

A

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

B

9ξ-hydroxy-(4arH.4bcH.8acH.10acH)-tetradecahydro-phenanthrene of mp: 111 degree

9ξ-hydroxy-(4arH.4bcH.8acH.10acH)-tetradecahydro-phenanthrene of mp: 111 degree

Conditions
ConditionsYield
Hydrogenation; (+-)-(4arH,10acH)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrol-(9ξ) of mp: 116 degree;
phenanthrene
85-01-8

phenanthrene

hydrogen

hydrogen

nickel

nickel

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
at 200℃;
phenanthrene
85-01-8

phenanthrene

hydrogen

hydrogen

palladium

palladium

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

Conditions
ConditionsYield
at 160℃;
phenanthrene
85-01-8

phenanthrene

A

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

B

1,2,3,4,5,6,7,8-Octahydrophenanthrene
5325-97-3

1,2,3,4,5,6,7,8-Octahydrophenanthrene

Conditions
ConditionsYield
With Dimethyldisulphide for 40h;
3,5,4'-trimethoxystilbene
22255-22-7, 94608-23-8, 63844-75-7

3,5,4'-trimethoxystilbene

A

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

B

1,2-dicyclohexylethane
3321-50-4

1,2-dicyclohexylethane

Conditions
ConditionsYield
With hydrogen; platinum(II) chloride In ethanol at 60℃; under 750.075 - 1500.15 Torr; for 6h;
dihydrophenanthrene
5743-97-5

dihydrophenanthrene

phenanthrene
85-01-8

phenanthrene

dihydrophenanthrene
5743-97-5

dihydrophenanthrene

1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydro-phenanthrene
113618-69-2

1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydro-phenanthrene

Conditions
ConditionsYield
With tetrachloromethane; ozone
dihydrophenanthrene
5743-97-5

dihydrophenanthrene

chromium (III)-oxide-aluminium oxide contacts

chromium (III)-oxide-aluminium oxide contacts

phenanthrene
85-01-8

phenanthrene

Conditions
ConditionsYield
at 450 - 550℃; isomer(ic) of doubtful homogeneity;
dihydrophenanthrene
5743-97-5

dihydrophenanthrene

benzene
71-43-2

benzene

nickel containing catalyst

nickel containing catalyst

phenanthrene
85-01-8

phenanthrene

Conditions
ConditionsYield
at 350℃; isomer(ic) of doubtful homogeneity;

5743-97-5Downstream Products

5743-97-5Relevant academic research and scientific papers

The solvent determines the product in the hydrogenation of aromatic ketones using unligated RhCl3as catalyst precursor

Bartling, Stephan,Chakrabortty, Soumyadeep,De Vries, Johannes G.,Kamer, Paul C. J.,Lund, Henrik,Müller, Bernd H.,Rockstroh, Nils

, p. 7608 - 7616 (2021/12/13)

Alkyl cyclohexanes were synthesized in high selectivity via a combined hydrogenation/hydrodeoxygenation of aromatic ketones using ligand-free RhCl3 as pre-catalyst in trifluoroethanol as solvent. The true catalyst consists of rhodium nanoparticles (Rh NPs), generated in situ during the reaction. A range of conjugated as well as non-conjugated aromatic ketones were directly hydrodeoxygenated to the corresponding saturated cyclohexane derivatives at relatively mild conditions. The solvent was found to be the determining factor to switch the selectivity of the ketone hydrogenation. Cyclohexyl alkyl-alcohols were the products using water as a solvent.

Aromatic compound hydrogenation and hydrodeoxygenation method and application thereof

-

Paragraph 0094-0095; 0123-0125; 0127-0130, (2021/05/29)

The invention belongs to the technical field of medicines, and discloses an aromatic compound hydrogenation and hydrodeoxygenation method under mild conditions and application of the method in hydrogenation and hydrodeoxygenation reactions of the aromatic compounds and related mixtures. Specifically, the method comprises the following steps: contacting the aromatic compound or a mixture containing the aromatic compound with a catalyst and hydrogen with proper pressure in a solvent under a proper temperature condition, and reacting the hydrogen, the solvent and the aromatic compound under the action of the catalyst to obtain a corresponding hydrogenation product or/and a hydrodeoxygenation product without an oxygen-containing substituent group. The invention also discloses specific implementation conditions of the method and an aromatic compound structure type applicable to the method. The hydrogenation and hydrodeoxygenation reaction method used in the invention has the advantages of mild reaction conditions, high hydrodeoxygenation efficiency, wide substrate applicability, convenient post-treatment, and good laboratory and industrial application prospects.

Mesoporous zeolite-supported metal sulfide catalysts with high activities in the deep hydrogenation of phenanthrene

Fu, Wenqian,Zhang, Lei,Wu, Dongfang,Xiang, Mei,Zhuo, Qian,Huang, Kai,Tao, Zhongdong,Tang, Tiandi

, p. 423 - 433 (2015/09/02)

Developing highly active hydrogenation catalysts for deep aromatics saturation is of great importance in the production of ultraclean diesel fuel at a low cost. Toward this goal, we synthesized a mesoporous zeolite ZSM-5 (MZSM-5) that was cost-effective and available on a large scale, and used it as a support for the preparation of highly efficient metal sulfide catalysts (NiMoS/MZSM-5 and CoMoS/MZSM-5) for the deep hydrogenation of phenanthrene. The intrinsic activity of the NiMoS/MZSM-5 catalyst (7.4 × 10-4 mol kg-1 s-1) was much higher than that of the alumina-supported NiMo catalyst (NiMoS/γ-Al2O3, 4.8 × 10-4 mol kg-1 s-1), and the selectivity of the deep hydrogenation products over NiMoS/MZSM-5 (20.9%) was higher than for NiMoS/γ-Al2O3 (15.2%). Compared with γ-Al2O3, the relatively weak metal-support interaction could facilitate the formation of polymolybdates on MZSM-5. After sulfidation, the more multistacked MoS2 active phases were formed on the MZSM-5, enhancing the hydrogenation activity of the NiMoS/MZSM-5 catalyst.

Preferential catalytic hydrogenation of aromatic compounds versus ketones with a palladium substituted polyoxometalate as pre-catalyst

Kogan, Vladimir,Aizenshtat, Zeev,Neumann, Ronny

, p. 272 - 274 (2007/10/03)

A palladium-substituted polyoxometalate having a Keggin structure, supported on γ-alumina or active carbon, was used as a catalyst precursor for catalytic hydrogenation. The catalyst system enabled fast hydrogenation of arenes at 30 bar H2 and 230°C. Most interesting was the finding that arenes could be selectively reduced in the presence of distal ketone groups under similar conditions, 30 bar H2 and 200°C. For example, 1-phenyl-2-propanone yielded 1-cyclohexyl-2-propanone with no reduction of the ketone moiety. Additionally, aromatic compounds with vicinal (conjugated) ketone moieties underwent complete hydrogenation to saturated hydrocarbons and catalytic McMurry coupling was observed for aliphatic aldehydes.

Vapor pressure and liquid heat capacity of perhydroacenaphthylene and perhydrophenanthrene

Rohac, Vladislav,Censky, Miroslav,Zala, Diana,Ruzicka, Vlastimil,Ruzicka, Kvetoslav,Sporka, Karel,Aim, Karel

, p. 1205 - 1210 (2007/10/03)

Saturated vapor pressures and liquid heat capacities have been measured for liquid perhydroacenaphthylene and perhydrophenanthrene by comparative ebulliometry over an approximate pressure range from (8 to 100) kPa and by heat conduction calorimetry over a temperature range from about (305 to 335) K. The obtained results for vapor pressures and for heat capacities have been represented within experimental uncertainties by the Antoine and the Cox equations and by an empirical polynomial equation, respectively, and compared with the data available in the literature.

HYDROLIQUEFACTION OF COAL AND HYDROGENATION OF PHENANTHRENE WITH IRON CATALYSTS ACTIVATED BY NEW METHOD

Ogata, Eisuke,Hatakeyama, Kazuya,Kamiya, Yoshio

, p. 1913 - 1916 (2007/10/02)

Iron catalysts obtained by the CO pretreatment of iron oxide and iron ore suspended in hydrocarbon solvents presented high catalytic activities for the hydroliquefaction of coal and hydrogenation of phenanthrene.

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