4904-61-4

Basic information

• Product Name: Cyclododeca-1,5,9-triene
• Synonyms: (z,e,e)-cdt;1,5,9-Cyclododecatriene (Z,E,E);1,5,9-cyclododecatriene(z,e,e);1,5,9-Cyclooctatriene;CDDT;cis,trans,trans-Cyclododeca-1,5,9-triene;Cyclododecatriene;TRANS,TRANS,TRANS-CYCLODODECA-1,5,9-TRIENE
• CAS NO: 4904-61-4
• Molecular Formula: C₁₂H₁₈
• Molecular Weight: 162.27
• EINECS: 225-533-8
• Mol File: 4904-61-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 33-35 °C(lit.)
• Boiling Point: 237-238 °C(lit.)
• Flash Point: 178 °F
• Appearance: colorless liquid
• Density: 0.89 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0602mmHg at 25°C
• Refractive Index: 1.5082 (estimate)
• Storage Temp.: 2-8°C
• Water Solubility: 280μg/L at 20℃
• CAS DataBase Reference: Cyclododeca-1,5,9-triene(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclododeca-1,5,9-triene(4904-61-4)
• EPA Substance Registry System: Cyclododeca-1,5,9-triene(4904-61-4)

Safety Data

• Hazard Codes: C,N,Xn
• Statements: 34-65-50/53
• Safety Statements: 26-36/37/39-45-62-61-60
• RIDADR: UN 2518 6.1/PG 3
• WGK Germany: 3
• RTECS: GU2310000
• Hazardous Substances Data: 4904-61-4(Hazardous Substances Data)

Usage

General Description

A colorless liquid. Toxic by skin absorption and ingestion and irritating to skin and eyes. Used to make other chemicals.

Reactivity Profile

Cyclododeca-1,5,9-triene may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions.

Health Hazard

Exposure can cause irritation and burns of eyes, nose and throat.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C12H18/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-2,7-10H,3-6,11-12H2/b2-1-,9-7-,10-8-

Synthetic route

styrene (100-42-5) + buta-1,3-diene (106-99-0) → 1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) + cyclododeca-1,5,9-triene (4904-61-4) + 1-phenyl-1,4,8(9)-decatriene (13107-72-7)

Conditions	Yield
With Ni acetylacetonate; triethylaluminum; triphenylphosphine In toluene at 90℃; for 1.41667h; Kinetics; Mechanism; Product distribution; other temperature; various ratio of components. Other object of study: the rate constants;	A 11.2 % Turnov. B 10.2 % Turnov. C 78.6 % Turnov.

buta-1,3-diene (106-99-0) → 1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) + vinylcyclohexane (695-12-5) + cyclododeca-1,5,9-triene (4904-61-4)

Conditions	Yield
at 80℃; for 5h; Product distribution; also in presence aprotic solvents, var, times, temp.;

buta-1,3-diene (106-99-0) → 1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) + octa-1,3,7-triene (1002-35-3) + 5-methyl-hepta-1,3,6-triene (925-52-0) + 4-ethenylcyclohexene (100-40-3) + cyclododeca-1,5,9-triene (4904-61-4)

Conditions	Yield
With iron(III)-acetylacetonate; C17H34O2P2; triethylaluminum In benzene at 50℃; for 4h; Product distribution; Pressure (range begins): 730 ;

buta-1,3-diene (106-99-0) → 5-methyl-hepta-1,3,6-triene (925-52-0) + cyclododeca-1,5,9-triene (4904-61-4)

Conditions	Yield
With iron(III)-acetylacetonate; PC-P(OBu-t)2; triethylaluminum In benzene at 50℃; for 1h; Product distribution; Pressure (range begins): 730 ;

styrene (100-42-5) + butadiene oligomers → 4-ethenylcyclohexene (100-40-3) + cyclododeca-1,5,9-triene (4904-61-4) + n-dodeca-2,4,6,10-tetraene + copolymer of butadiene oligomers with styrene

Conditions	Yield
With tert.-butylhydroperoxide at 165℃; for 24h; Product distribution; Further Variations:; Reagents; Temperatures; copolymerization;

buta-1,3-diene (106-99-0) → cyclododeca-1,5,9-triene (4904-61-4) + polybutadiene

Conditions	Yield
ethylaluminum sesquichloride; water; titanium tetrachloride In benzene at 60℃; under 1500.15 Torr; Product distribution / selectivity;
ethylaluminum sesquichloride; ammonia; water; titanium tetrachloride In benzene at 46 - 60℃; under 1500.15 Torr; Product distribution / selectivity;
ethylaluminum sesquichloride; ammonia; water; titanium tetrachloride In benzene at 60℃; under 1500.15 Torr; Product distribution / selectivity;
ethylaluminum sesquichloride; ammonia; water; titanium tetrachloride In 1-vinylcyclohexene; 1,3-cyclooctadiene at 60℃; under 1500.15 Torr; Product distribution / selectivity;
ethylaluminum sesquichloride; ammonia; titanium tetrachloride In benzene at 60℃; under 1500.15 Torr; Product distribution / selectivity;

cyclododeca-1,5,9-triene (4904-61-4) → cyclododecane (294-62-2) + cyclododecene (1501-82-2) + cyclododeca-1,5-diene (1502-04-1, 67881-13-4)

Conditions	Yield
With hydrogen at 80 - 160℃; under 760.051 Torr; Reagent/catalyst; Flow reactor;	A 100% B n/a C n/a
With hydrogen; Ru4Sn6/Davison 923 mesoporous silica at 119.84℃; under 22502.3 Torr; for 12h; Product distribution; Further Variations:; reaction times;

styrene (100-42-5) + 4-ethenylcyclohexene (100-40-3) + cyclododeca-1,5,9-triene (4904-61-4) + n-dodeca-2,4,6,10-tetraene → polymer, average characteristics Mn 2570 Da, Mw 5080 Da, Mz 8020 Da; monomer(s): styrene; 4-vinylcyclohexene; 1,5,9-cyclododecatriene; n-dodeca-2,4,6,10-tetraene

Conditions	Yield
With tert.-butylhydroperoxide In octane; toluene at 160℃; for 18h;	99.2%

cyclododeca-1,5,9-triene (4904-61-4) → cyclododeca-1,5-diene (1502-04-1, 67881-13-4)

Conditions	Yield
With hydrogen at 240℃; under 760.051 Torr; for 0.000916667h;	96%
With hydrogen In methanol at 20℃; under 750.075 Torr; Catalytic behavior; Green chemistry;

cyclododeca-1,5,9-triene (4904-61-4) → 1,2,5,6,9,10-hexabromocyclododecane (3194-55-6)

Conditions	Yield
With bromine In dichloromethane; 2-methyl-propan-1-ol; chloroform at 14 - 15℃; pH=7; Large scale;	96%
With bromine; sodium bromide In 2-methyl-propan-1-ol; chloroform; water at 10 - 15℃; for 4.5h; Solvent; Reagent/catalyst; Cooling with ice;	94.9%
With hydrogen bromide; bromine In 2-ethoxy-ethanol at 50 - 90℃; for 17h; Temperature;	92%
With 1-(-sulfonato)propyl-3-propanesulfonic acid imidazolium; hydrogen bromide; bromine In 2-ethoxy-ethanol at 50 - 90℃; for 8h; Temperature;	90%
With bromine In 2-methyl-propan-1-ol; 1,2-dichloro-ethane at 30 - 50℃; for 5.25h;

cyclododeca-1,5,9-triene (4904-61-4) → 1.2.4- trivinylcyclohexane (2855-27-8)

Conditions	Yield
at 507℃; under 740 Torr; for 1h; Pressure; Temperature; Time; Inert atmosphere;	76.7%

cyclododeca-1,5,9-triene (4904-61-4) → Cyclododecadien-(5,9)-diol-(1,2) (15786-26-2)

Conditions	Yield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In dichloromethane; water at 20℃; for 24h;	76%
Stage #1: cyclododeca-1,5,9-triene With pyridine; osmium(VIII) oxide In ethanol at 0℃; for 2h; Stage #2: With sodium hydrogensulfite In ethanol at 20℃; for 12h;
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane 2: water View Scheme

cyclododeca-1,5,9-triene (4904-61-4) → cyclododecane (294-62-2)

Conditions	Yield
With sodium tetrahydroborate; hydrogen; nickel dichloride In isopropyl alcohol at 50℃; under 760.051 Torr; for 6h;	68%
With hydrogen; oxohalogenophosphinerhenium complexes In toluene at 165℃; under 38000 Torr; Product distribution; different catalysts; other molar ratio PPh3 : catalyst;

cyclododeca-1,5,9-triene (4904-61-4) → cyclododecene (1501-82-2) + cyclododeca-1,5-diene (1502-04-1, 67881-13-4)

Conditions	Yield
With hydrogen at 240℃; under 760.051 Torr; for 0.000638889h;	A 65% B 25%
Stage #1: cyclododeca-1,5,9-triene With hydrogen; 0.5% palladium on alumina at 120℃; under 825.083 Torr; Industry scale; Gas phase; Stage #2: 0.5% palladium on alumina Product distribution / selectivity;	A n/a B 0.2%
Stage #1: cyclododeca-1,5,9-triene With carbon monoxide; hydrogen; 0.5% palladium on alumina at 120℃; under 825.083 Torr; Industry scale; Gas phase; Stage #2: 0.5% palladium on alumina Product distribution / selectivity;	A n/a B 0.2%
With hydrogen; Ru4Sn6/Davison 923 mesoporous silica at 99.84℃; under 22502.3 Torr; for 8h; Product distribution; Further Variations:; Catalysts; Temperatures;

cyclododeca-1,5,9-triene (4904-61-4) → 1,2-epoxy-5,9-cyclododecadiene (943-93-1)

Conditions	Yield
With oxygen; isobutyraldehyde In acetonitrile at 60℃; for 4h;	53%
Stage #1: cyclododeca-1,5,9-triene With Aliquat 336 Under N2; Stirring; Heating up to 75 °ree;C; Stage #2: With phosphoric acid; dihydrogen peroxide; sodium tungstate In water at 75℃; for 1.5h; 60 % aq. H2O2 was added at 75 °ree;C; Na2WO4 and H3PO4 were added over a time of 25 min;	163.1 g
Stage #1: cyclododeca-1,5,9-triene Under N2; Stirring; Heating up to 75 °ree;C; Stage #2: With phosphoric acid; dihydrogen peroxide; sodium tungstate In water at 75℃; for 1.5h; 60 % aq. H2O2 was added at 75 °ree;C; Na2WO4 and H3PO4 were added over a time of 25 min;	160.6 g

cyclododeca-1,5,9-triene (4904-61-4) + 1,2-dihydroacenaphthylene-1,2-diol (17976-92-0) → (6bRS,7RS,7aRS,13aSR,14SR,14aRS)-7,7a,8,9,10,11,12,13,13a,14-decahydro-7,14-ethenocycloocta[k]fluoranthene-6b,14a-diol

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; 1,2-bis-(diphenylphosphino)ethane at 130℃; for 40h; Sealed tube; Inert atmosphere; diastereoselective reaction;	43%

tetrachloromethane (56-23-5) + cyclododeca-1,5,9-triene (4904-61-4) → 1-hydroxy-2-(trichloromethyl)cyclododecadiene-5,9 (1207726-79-1) + 1-chloro-2-(trichloromethyl)cyclododecadiene-5,9 (1855-53-4)

Conditions	Yield
With chromium(III) acetylacetonate; water In acetonitrile at 130℃; for 6h; Autoclave;	A 6% B 24%

cyclododeca-1,5,9-triene (4904-61-4) + sodium chlorodifluoroacetate (1895-39-2) → (4Z,8Z)-13,13-difluoro-bicyclo[10.1.0]trideca-4,8-diene (1269640-17-6) + (9E)-5,5,14,14-tetrafluoro-tricyclo[11.1.0.04,6]tetradec-9-ene (1269662-62-5)

Conditions	Yield
at 190℃; Pyrolysis;	A 4.2% B 13.8%

methanol (67-56-1) + formic acid (64-18-6) + cyclododeca-1,5,9-triene (4904-61-4) → Octahydro-cyclopenta[d]indene-3a-carboxylic acid methyl ester (37974-01-9)

Conditions	Yield
(i) H2SO4, CCl4, (ii) /BRN= 1098229/; Multistep reaction;

cyclododeca-1,5,9-triene (4904-61-4) + phenylsilane (694-53-1) → 9-Phenylsilyl-1.5-cyclododecadien

Conditions	Yield
With dibenzoyl peroxide In n-heptane

cyclododeca-1,5,9-triene (4904-61-4) → 10-Chlor-cyclododecadien-(1,5)-on-(9)-oxim (949-08-6)

Conditions	Yield
With hydrogenchloride; nitrosylchloride In diethyl ether

cyclododeca-1,5,9-triene (4904-61-4) + dimethyl amine (124-40-3) → 1-Dimethylamino-cyclododecadien-(5,9)-on-2-oxim (18216-23-4)

Conditions	Yield
(i) NOCl, (ii) /BRN= 605257/, aq. MeOH; Multistep reaction;

cyclododeca-1,5,9-triene (4904-61-4) → cyclododecene (1501-82-2)

Conditions	Yield
With hydrogen; nickel(II) In methanol at 150℃; under 36752.9 Torr; var. solvents, var. catalysts Co and Ni complexes; other object of study- activity of catalysts;
With ruthenium trichloride; formaldehyd; hydrogen; acetic acid; triphenylphosphine In ethanol; water at 25 - 160℃; under 7500.75 - 15001.5 Torr; for 6.66667h;
With ruthenium trichloride; formaldehyd; hydrogen; acetic acid; triphenylphosphine In ethanol; water at 25 - 160℃; under 7500.75 - 15001.5 Torr; for 6.66667h;
With ruthenium trichloride; formaldehyd; hydrogen; acetic acid; triphenylphosphine In ethanol at 160℃; under 15001.5 Torr; Temperature; Pressure;

cyclododeca-1,5,9-triene (4904-61-4) → 12-oxododecanenitrile (13050-14-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) NOCl, (ii) /BRN= 605257/, aq. MeOH 2: H2 / Pd-C / ethanol 3: SO3 / liquid sulphur dioxide / -30 °C View Scheme

cyclododeca-1,5,9-triene (4904-61-4) → cyclododecanone oxime (946-89-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NOCl, HCl / diethyl ether 2: H2 / Pd-C / methanol View Scheme
Multi-step reaction with 4 steps 1: dihydrogen peroxide / phosphotungstic acid; Aliquat 336 / water 2: hydrogen / platinum on activated charcoal 3: lithium iodide / 230 °C 4: hydroxyammonium sulfate; ammonia; sulfuric acid; ammonium sulfate / toluene; water / 85 °C / pH 4 - 5.8 / Industry scale View Scheme
Multi-step reaction with 3 steps 1.1: ruthenium trichloride; triphenylphosphine; acetic acid; formaldehyd; hydrogen / water; ethanol / 6.67 h / 25 - 160 °C / 7500.75 - 15001.5 Torr 2.1: dinitrogen monoxide / cyclohexane / 6 h / 300 - 350 °C / 75007.5 Torr / Flow reactor 3.1: ammonium acetate / ethanol / 80 °C 3.2: 0.5 h / 1350.14 Torr View Scheme
Multi-step reaction with 3 steps 1.1: triphenylphosphine; ruthenium trichloride; acetic acid; formaldehyd; hydrogen / water; ethanol / 6.67 h / 25 - 160 °C / 7500.75 - 15001.5 Torr 2.1: dinitrogen monoxide / 1 h / Flow reactor 3.1: ammonium acetate; ammonia / ethanol / 0.5 h / 80 °C / 1350.14 Torr / Flow reactor 3.2: Flow reactor View Scheme

cyclododeca-1,5,9-triene (4904-61-4) → 9-Aminocyclododecadien-(1,5) (72193-55-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: NOCl, HCl / diethyl ether 2: LiAlH4 / diethyl ether View Scheme

cyclododeca-1,5,9-triene (4904-61-4) → 1-Dimethylamino-cyclododecanon-2-oxim (18216-22-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) NOCl, (ii) /BRN= 605257/, aq. MeOH 2: H2 / Pd-C / ethanol View Scheme

cyclododeca-1,5,9-triene (4904-61-4) → cyclododecane (294-62-2) + cyclododecene (1501-82-2)

Conditions	Yield
With hydrogen; Ru4Sn6/Davison 923 mesoporous silica at 139.84℃; under 22502.3 Torr; for 8h; Product distribution; Further Variations:; Catalysts; Temperatures;

Upstream product

• 51097-60-0 (Z)-oct-4-enedial 
• 15546-42-6 [1,1'-(butane-1,4-diyl)bis(triphenylphosphonium)] dibromide 
• 106-99-0 buta-1,3-diene 
• 4526-07-2 1,4-bis(trimethylsilyl)-1,3-butadiyne 
• 100-42-5 styrene 

Downstream Products

• 1501-82-2 cyclododecene 
• 1502-04-1 cyclododeca-1,5-diene 
• 4744-26-7 5.6:9.10-Diepoxy-cyclododecen-⁽¹⁾ 
• 943-93-1 1,2-epoxy-5,9-cyclododecadiene 
• 3194-55-6 1,2,5,6,9,10-hexabromocyclododecane 
• 2855-27-8 1,trans-2,cis-4-trivinylcyclohexane 
• 2855-27-8 1.2.4- trivinylcyclohexane 
• 947-04-6 2-azacyclotridecanone 
• 830-13-7 cyclododecanone 
• 286-99-7 1,2-epoxycyclododecane 
• 1000399-22-3 cyclo-undeca-3,7-dienecarbaldehyde 
• 1000399-21-2 dodeca-4,8,11-trienal 
• 138024-39-2 trans-1,2-epoxy-cis,trans-5,9-cyclododecadiene 
• 15229-79-5 cyclododeca-4,8-dien-1-one 

Relevant articles and documents

PROCESS FOR PREPARING CYCLODODECATRIENE

Preparation of cyclododecatriene in a continuous or discontinuous process by trimerization of butadiene in the presence of a catalyst system and a solvent, the crude cyclododecatriene obtained being able to be isolated by means of distillation. The cyclooctadiene formed as by-product can likewise be isolated from the crude product.

Titanium-catalyzed [4+2] and [6+2] cycloadditions of 1,4-bis(trimethylsilyl)buta-1,3-diyne

The (C2H5)2AlCl/TiCl4 catalyst induces the [4+2] cycloaddition of butadiene or the [6+2] cycloaddition of 1,3,5-cycloheptatriene (CHT) to individual acetylenic moieties of 1,4-bis(trimethylsilyl)buta-1,3-diyne (BSD). Heating of the 2:1 butadiene adduct, bis(2-trimethylsilylcyclohexa-1,4-dien-1-yl), to 250°C yields 2,2′-bis(trimethylsilyl)biphenyl. The 1:1 adduct of BSD with CHT, 7-trimethylsilyl-8-trimethylsilylethynylbicyclo[4.2.1]nona-2,4-diene, is obtained as virtually the only product if the initial molar ratio CHT:BD equal to 1.86 is used.

OLIGOMERIZATION OF BUTADIENE IN THE PRESENCE OF METAL COMPOUNDS IMMOBILIZED ON POLYMERIC CARRIERS. COMMUNICATION 1. IRON COMPLEXES IMMOBILIZED IN THE BULK OF A POLYMER GEL IN THE REACTION OF LINEAR DIMERIZATION OF BUTADIENE

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