293-96-9

Basic information

• Product Name: CYCLODECANE
• Synonyms: CYCLODECANE;Cyclodecane, 98+%
• CAS NO: 293-96-9
• Molecular Formula: C₁₀H₂₀
• Molecular Weight: 140.27
• EINECS: 206-032-3
• Product Categories: Alkanes;Cyclic;Organic Building Blocks
• Mol File: 293-96-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 9-10 °C(lit.)
• Boiling Point: 201 °C(lit.)
• Flash Point: 149 °F
• Appearance: colourless liquid
• Density: 0.871 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.447mmHg at 25°C
• Refractive Index: n20/D 1.471(lit.)
• Water Solubility: 0.33mg/L(25 oC)
• Stability: Stable. Incompatible with strong oxidizing agents. Combustible.
• BRN: 1900637
• CAS DataBase Reference: CYCLODECANE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLODECANE(293-96-9)
• EPA Substance Registry System: CYCLODECANE(293-96-9)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 293-96-9(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 817, 1968 DOI: 10.1021/ja01005a063

InChI:InChI=1/C10H20/c1-2-4-6-8-10-9-7-5-3-1/h1-10H2

Synthetic route

Cyclohexanone diperoxide (183-84-6) → hexahydro-2H-oxepin-2-one (502-44-3) + oxacyclododecan-2-one (1725-03-7) + cyclodecane (293-96-9)

Conditions	Yield
With toluene-4-sulfonic acid In 2,2,2-trifluoroethanol at 25℃; for 0.666667h; Reagent/catalyst; Solvent; Temperature;	A 31.73% B 42.5% C n/a

6-hydroxycyclodecan-1-one (15957-40-1) → 11-oxa-bicyclo[4.4.1]undecane (281-66-3) + cyclodecane (293-96-9)

Conditions	Yield
With platinum on activated charcoal at 155℃; Hydrogenation;

2-hydroxycyclodecanone (96-00-4) → cyclodecane (293-96-9)

Conditions	Yield
With hydrogenchloride; amalgamated zinc; acetic acid

cyclodecyne (3022-41-1) → cyclodecane (293-96-9)

Conditions	Yield
With acetic acid; platinum Hydrogenation;

(+/-)-6-methoxycyclodecanone (76976-65-3) → 11-oxa-bicyclo[4.4.1]undecane (281-66-3) + cyclodecane (293-96-9)

Conditions	Yield
With platinum on activated charcoal at 155℃; Hydrogenation;

Cyclohexanone diperoxide (183-84-6) → oxacyclododecan-2-one (1725-03-7) + cyclodecane (293-96-9) + cyclohexanone (108-94-1)

Conditions	Yield
In benzene at 140℃; Rate constant; Product distribution; Mechanism; other temperatures; ΔH(excit.), ΔS(excit.);

cis,cis,cis-cyclodeca-1,3,5-triene (75993-36-1) → cyclodecane (293-96-9)

Conditions	Yield
With hydrogen

trans-tricyclo<7.1.0.04,6>deca-2,7-diene → cyclodecane (293-96-9) + bicyclo<7.1.0>decane (286-76-0, 66537-41-5) + trans-tricyclo<7.1.0.04,6>decane (286-73-7, 89955-58-8, 89955-59-9)

Conditions	Yield
With hydrogen; nickel In hexane at 60℃; under 60800 Torr; for 1h; Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; nickel In hexane at 60℃; under 60800 Torr; for 1h; Yield given. Yields of byproduct given;
With hydrogen; nickel In hexane at 60℃; under 60800 Torr; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Cyclodecene (3618-12-0) → cis-1,2-diethylcyclohexane (824-43-1) + cyclodecane (293-96-9) + trans-N,N'-dimethyl-1,2-cyclohexanediamine (824-43-1, 3642-13-5, 13990-95-9)

Conditions	Yield
With n-Undecane; (i-PrPCP)IrH2 at 196℃; for 0.5h; Catalytic hydrogenation; Isomerization; Title compound not separated from byproducts;

cyclodec-1c-en-6-yne → cyclodecane (293-96-9)

Conditions	Yield
With acetic acid; platinum Hydrogenation;

cyclodecadiene → cyclodecane (293-96-9)

Conditions	Yield
With diethyl ether; platinum Hydrogenation;

diethyl ether (60-29-7) + bromocyclodecane (2749-64-6) + iodine (7553-56-2) + magnesium → cyclodecane (293-96-9) + Cyclodecene (3618-12-0) + cyclodecanecarboxylic acid (3203-36-9) + dicyclodecyl (120620-90-8)

Conditions	Yield
anschliessend Behandeln mit festem Kohlendioxid;

cyclododecane (294-62-2) → 1-hexene (592-41-6) + propene (187737-37-7) + 1-dodecene (112-41-4) + ethene (74-85-1) + nona-1,8-diene (4900-30-5) + cyclodecane (293-96-9) + further products

Conditions	Yield
With water at 670 - 770℃; Thermodynamic data; Kinetics; Product distribution; further objects of study: mechanism, activation energy, frequency factor, dependence of ethylene yield distribution from temperature;

cyclodecane (293-96-9) → cyclodecanol (1502-05-2)

Conditions	Yield
With ferredoxin reductase; [2Fe–2S] ferredoxin; cytochrome P450 enzyme CYP101B1 In aq. buffer pH=7.4; Kinetics; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;	95%
With NADPH; P450 BM3 mutation of F87A/A328I enzyme In dimethyl sulfoxide for 1h; pH=7.5; aq. phosphate buffer; Enzymatic reaction;
Multi-step reaction with 2 steps 1: cytochrome P450 monooxygenase CYP101B1 from Novosphingobium aromaticivorans; ferredoxin reductase; NADH / aq. buffer / 2 h / 20 °C / pH 7.4 / Enzymatic reaction 2: sodium tetrahydroborate View Scheme

cyclodecane (293-96-9) → chlorocyclodecane (7541-62-0)

Conditions	Yield
With N-chloro-succinimide; benzophenone In acetonitrile at 27℃; for 24h; Irradiation; regioselective reaction;	95%

4,7-dichloroquinoline (86-98-6) + cyclodecane (293-96-9) → 4,7-dichloro-2-cyclodecylquinoline

Conditions	Yield
With sodium azide; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 4h;	87%

cyclodecane (293-96-9) + phenylethynyl diphenylphosphine oxide (7608-18-6) → 2-cyclodecyl-1,3-diphenyl-1H-phosphindole 1-oxide

Conditions	Yield
With di-tert-butyl peroxide; copper(I) bromide at 140℃; for 12h; Schlenk technique; Inert atmosphere;	80%

cyclodecane (293-96-9) + C19H16F3N2O2S(1+)*BF4(1-) → 4-cyclodecyl-2-phenylpyridine

Conditions	Yield
With 9,10-phenanthrenequinone In acetonitrile at 20℃; for 24h; UV-irradiation; Inert atmosphere;	80%

cyclodecane (293-96-9) + 2-isocyano-4’,5-dimethyl-1,1’-biphenyl → 6-cyclodecyl-2,8-dimethylphenanthridine (1620195-63-2)

Conditions	Yield
With copper(I) oxide; di-tert-butyl peroxide at 120℃; for 24h; Sealed tube;	75%

cyclodecane (293-96-9) → 1-fluorocyclodecane (860003-06-1)

Conditions	Yield
With Selectfluor; acetophenone In acetonitrile at 27℃; for 15h; Inert atmosphere; Irradiation;	73%
With copper(l) iodide; N-hydroxyphthalimide; N,N'-bis(benzyliden)ethylendiamine; Selectfluor; potassium iodide; potassium tetrakis(pentafluorophenyl)borate In acetonitrile at 81℃; for 0.5h; Reagent/catalyst; Inert atmosphere;	47%
With 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate; 1,2,4,5-tetracyanobenzene In acetonitrile for 16h; Inert atmosphere; UV-irradiation;	64 %Spectr.
With copper(l) iodide; potassium carbonate; Selectfluor; N,N'-(ethane-1,2-diyl)bis(1-(2,6-dichlorophenyl)methanimine) In [D3]acetonitrile at 20℃; for 0.0333333h; Reagent/catalyst; Inert atmosphere;
With triethyl borane; Selectfluor In hexane; acetonitrile at 20℃; for 4h; Inert atmosphere;	40 %Spectr.

cyclodecane (293-96-9) + 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one → (cyclodecylethynyl)triisopropylsilane

Conditions	Yield
With di-tert-butyl peroxide at 100℃; for 16h; Schlenk technique; Inert atmosphere;	67%

cyclodecane (293-96-9) + methyl isoquinoline-3-carboxylate (27104-73-0) → C21H27NO2

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride; 4,5,6,7-tetrafluoro-1-hydroxybenzo[d][1,2]iodaoxol-3(1H)-one In dichloromethane at 30℃; Minisci Aromatic Substitution; Inert atmosphere; Irradiation; chemoselective reaction;	67%

trifluoromethylsulfinyl chloride (20621-29-8) + cyclodecane (293-96-9) → cyclodecyl(trifluoromethyl)sulfane

Conditions	Yield
With dipotassium peroxodisulfate; triphenylphosphine; silver carbonate In acetonitrile at 60℃; for 12h; Inert atmosphere; Sealed tube;	58%
With silver (II) carbonate; dipotassium peroxodisulfate; triphenylphosphine In acetonitrile at 60℃; for 12h; Sealed tube; Inert atmosphere;	61 %Spectr.

cyclodecane (293-96-9) → 1,10-decanedioic acid (111-20-6)

Conditions	Yield
With N-hydroxyphthalimide; bis(acetylacetonato)manganese(II); oxygen; acetic acid at 100℃; under 760.051 Torr; for 14h;	55%
With nitric acid

cyclodecane (293-96-9) + silver(I) trifluoromethanethiolate (811-68-7) → cyclodecyl(trifluoromethyl)sulfane

Conditions	Yield
With dipotassium peroxodisulfate In acetonitrile at 60℃; for 12h; Inert atmosphere; Sealed tube;	55%

cyclohexenone (930-68-7) + cyclodecane (293-96-9) → 3-cyclododecylcyclohexanone

Conditions	Yield
With benzophenone In benzene for 26h; Irradiation;	52%

cyclopent-2-enone (930-30-3) + cyclodecane (293-96-9) → 3-cyclododecylcyclopentanone

Conditions	Yield
With benzophenone In benzene for 15h; Irradiation;	48%

cyclodecane (293-96-9) → cyclodecanone (1502-06-3)

Conditions	Yield
With dihydrogen peroxide; vanadium phosphorus oxide In acetonitrile at 70℃; for 20h;	28%
With dihydrogen peroxide; iron(III) chloride In pyridine; acetic acid Mechanism;
With cis-VI(6,6'-Cl2bpy)2O2> In tetrachloromethane; acetonitrile at 20℃; for 0.5h; Oxidation;	75 % Chromat.

cyclodecane (293-96-9) → perfluorocyclodecane (95896-73-4)

Conditions	Yield
With fluorine; sodium fluoride at -40 - 60℃;	14%

cyclodecane (293-96-9) → azulene (275-51-4)

Conditions	Yield
With pyrographite at 420 - 480℃; oder an Palladium/Kohle;

cyclodecane (293-96-9) + phenyl(bromodichloromethyl)mercury (3294-58-4) → (Dichlormethyl)-cyclodecan (52188-71-3)

methanol (67-56-1) + cyclodecane (293-96-9) → Cyclodecylmethanol (3668-38-0) + dicyclodecyl (120620-90-8) + ethylene glycol (107-21-1)

Conditions	Yield
With mercury at 64℃; for 17h; Irradiation; Yield given. Yields of byproduct given;

cyclodecane (293-96-9) → cis-decalin (493-01-6) + (Z)-cyclodecene (935-31-9) + trans-cyclodecene (2198-20-1) + cis-bicyclo<5.3.0>decane (16189-46-1)

Conditions	Yield
at 25℃; Product distribution; Irradiation; generation of cycloalkyl radicals and carbenes from various cycloalkanes and their termination reactions during radiolysis and photolysis;	A 6 % Chromat. B 28 % Chromat. C 47 % Chromat. D 19 % Chromat.
at 25℃; Irradiation; radiolysis; Yield given. Further byproducts given. Yields of byproduct given;
at 25℃; Irradiation; Further byproducts given;	A 5 % Chromat. B 28 % Chromat. C 47 % Chromat. D 20 % Chromat.

cyclodecane (293-96-9) → (Z)-cyclodecene (935-31-9) + trans-cyclodecene (2198-20-1) + cis-bicyclo<5.3.0>decane (16189-46-1) + dicyclodecyl (120620-90-8)

Conditions	Yield
at 25℃; Irradiation; radiolysis; Further byproducts given. Yields of byproduct given;

cyclodecane (293-96-9) → dicyclodecyl (120620-90-8)

Conditions	Yield
With mercury at 35℃; for 1h; Rate constant; Irradiation; substrate pressure 1 Torr, dehydrodimerization;
With mercury at 35℃; for 1h; Irradiation;

Upstream product

• 15957-40-1 6-hydroxycyclodecan-1-one 
• 96-00-4 2-hydroxycyclodecanone 
• 3022-41-1 cyclodecyne 
• 76976-65-3 (+/-)-6-methoxycyclodecanone 
• 183-84-6 Cyclohexanone diperoxide 
• 75993-36-1 cis,cis,cis-cyclodeca-1,3,5-triene 
• 3618-12-0 Cyclodecene 
• 60-29-7 diethyl ether 
• 2749-64-6 bromocyclodecane 
• 7553-56-2 iodine 
• 294-62-2 cyclododecane 

Downstream Products

• 111-20-6 1,10-decanedioic acid 
• 275-51-4 azulene 
• 34557-54-5 methane 
• 74-84-0 ethane 
• 74-98-6 propane 
• 110-54-3 hexane 
• 106-97-8 n-butane 
• 109-66-0 pentane 
• 187737-37-7 propene 
• 74-85-1 ethene 
• 109-67-1 1-penten 
• 872-05-9 1-Decene 
• 292-64-8 Cyclooctan 
• 1502-06-3 cyclodecanone 

Relevant articles and documents

TRIPLET PHOTOCHEMISTRY OF MEDIUM RING TRIENES

The photochemistry of the triplets of 10- and 11-membered ring 1,3,5-trienes has been studied.At -70 deg C, cis,trans,cis-cyclodeca-1,3,5-triene goes only to the cis,cis,cis-isomer.At 25 deg C, this latter compound is converted into cis-bicyclodeca-2,4-diene via the thermally labile trans,cis,trans-cyclodeca-1,3,5-triene.At -70 deg C, cis,trans,cis-cycloundeca-1,3,5-triene is converted to the cis,cis,cis-isomer.At 25 deg C, this primary photochemical product undergoes a thermal 1,7-sigmatropic hydrogen migration to yield the trans,cis,cis-isomer.This latter triene upon sensitized irradiation yields cis-bicycloundeca-8,10-diene and trans-bicycloundeca-2,10-diene.The ratio of these latter two products changes with the temperature of the sensitized reaction.The possible mechanisms of these transformations are discussed.

Preparation method of 11- andrographolide compound and caprolactone compound (by machine translation)

To the method, cyclohexenone spiro-11 - peroxide is used as a raw material, a protic acid is used as a catalyst, fluorine alcohol is used as a solvent, and the reaction temperature is in a range of from 25 °C~60 °C about. The method has the advantages of high yield, low cost, convenience in operation, mild reaction conditions and the like, and is convenient for industrial application. (by machine translation)

Mechanism of the thermal decomposition of substituted tetraoxanes in benzene solution: Effect of substituents on the activation parameters of the unimolecular reactions

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On the Pyrolysis of Unsubstituted Cyclanes - Selectivity of the Formation of Reaction Products, Kinetic Parameters, Mechanistic Interpretations

The thermal decomposition of cyclopentane (1), cyclohexane (2), cycloheptane (3), cyclooctane (4), cyclodecane (5), and cyclododecane (6) was studied in a laboratory-scale metallic tubular reactor at 650 to 850 deg C in the presence of steam.The kinetic parameters for the overall reactions were determined and the gaseous as well as the liquid reaction products were analyzed and identified by gas chromatography or by the coupling of gas chromatography and mass spectrometry, respectively.It could be shown that from all cyclanes the isomeric α-olefines are formed, if the conversion of the starting cyclanes is small.This supports the view that the cyclane - α-olefin isomerization is an important initial reaction in pyrolysis of 1 up to 6.The results also demonstrate that the main pathway of degradation is a radical chain mechanism via cyclanyl radicals with β(C-C) bond scission and 1.4 or 1.5-H-isomerization of alkenyl radicals as the most important reaction steps.