Product Name

  • Name

    1,3-Cyclopentadiene

  • EINECS 208-835-4
  • CAS No. 542-92-7
  • Article Data461
  • CAS DataBase
  • Density 0.878 g/cm3
  • Solubility 10.3 mM at 25 °C (shake flask-UV spectrophotometry, Streitwieser and Nebenzahl, 1976)
  • Melting Point - 97.2 C
  • Formula C5H6
  • Boiling Point 41.499 °C at 760 mmHg
  • Molecular Weight 66.1026
  • Flash Point
  • Transport Information
  • Appearance colourless liquid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 542-92-7 (1,3-Cyclopentadiene)
  • Hazard Symbols
  • Synonyms Cyclopentadiene;Pentole;Pyropentylene;R-Pentine;
  • PSA 0.00000
  • LogP 1.50250

Synthetic route

cyclopentene
142-29-0

cyclopentene

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
With n-butyllithium; potassium 2-methylbutan-2-olate In hexane 1) r.t., 14 h, 2) reflux, 5 h;100%
at 850℃; Erhitzen unter vermindertem Druck;
With chromium (III)-oxide-aluminium oxide contacts at 450 - 500℃;
With palladium at 180 - 200℃;
trimethylsilylcyclopentadiene
3559-74-8

trimethylsilylcyclopentadiene

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
With trifluoroacetic acid at 60℃; for 3h; Heating;100%
With potassium tert-butylate In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 3h;100%
manganocene
73138-26-8

manganocene

carbon dioxide
124-38-9

carbon dioxide

diethylamine
109-89-7

diethylamine

A

Mn(O2CN(C2H5)2)2

Mn(O2CN(C2H5)2)2

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In toluene under N2 or Ar;suspn. of Mn(cp)2 in toluene treated with stoicheiometric amt. of amine, clear soln, addn. of CO2, after 2 h no gas was uptaken; evapn.,;A 99%
B n/a
1,3-dihydroxycyclopentane
16326-97-9, 16326-98-0, 59719-74-3

1,3-dihydroxycyclopentane

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
With Nafion In water at 140℃; Temperature; Solvent; Reagent/catalyst;99%
With H-USY zeolite In tetrahydrofuran at 249.84℃; Inert atmosphere;93.8%
(η-cyclopentadienyl)(η-cyclopentadiene)nickel tetrafluoroborate
84651-76-3

(η-cyclopentadienyl)(η-cyclopentadiene)nickel tetrafluoroborate

triphenylantimony
603-36-1

triphenylantimony

A

[Ni(C5H5)(Sb(C6H5)3)2](1+)*BF4(1-)=[Ni(C5H5)(Sb(C6H5)3)2]BF4
85836-36-8

[Ni(C5H5)(Sb(C6H5)3)2](1+)*BF4(1-)=[Ni(C5H5)(Sb(C6H5)3)2]BF4

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In diethyl ether under Ar, Ni complex in ether mixed with stibane ligand (molar ratio 1:2), stirred for 5 h at room temp.; filtered, washed with ether, dried in vac., elem. anal.;A 98%
B n/a
vanadocene

vanadocene

lead(IV) tetraacetate
546-67-8

lead(IV) tetraacetate

A

{(η5-cyclopentadienyl)vanadium diacetate}2

{(η5-cyclopentadienyl)vanadium diacetate}2

B

lead acetate
301-04-2

lead acetate

C

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In toluene molar ratio Cp2V/Pb-compound 1/1, sealed ampoule, 20°C, 48 h;A 97%
B n/a
C 36.6%
Conditions
ConditionsYield
Heating;96%
at 180℃;
In decalin at 180℃; Diels-Alder Cycloaddition; Inert atmosphere;
bi(cyclopentadiene)
77-73-6, 933-60-8, 1755-01-7

bi(cyclopentadiene)

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
at 160℃;95%
at 350 - 400℃;91%
at 210℃;84.5%
endo-4a-acetyl-2,3-dichloro-4a,5,8,8a-tetrahydro-5,8-methano-1,4-naphthoquinone
79756-02-8, 79813-47-1

endo-4a-acetyl-2,3-dichloro-4a,5,8,8a-tetrahydro-5,8-methano-1,4-naphthoquinone

A

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

4-acetyl-6,7,7',8'-tetrachloro-3'aR*,9'bR*-dihydro-5,6',9'-trihydroxy-spiro<3H-benzofuran-2S*,5'(1'H)-cyclopenta<2>benzopyran>
79756-04-0

4-acetyl-6,7,7',8'-tetrachloro-3'aR*,9'bR*-dihydro-5,6',9'-trihydroxy-spiro<3H-benzofuran-2S*,5'(1'H)-cyclopenta<2>benzopyran>

Conditions
ConditionsYield
In benzene-d6 at 80℃; for 6h; sealed n.m.r. sample tube;A n/a
B 95%
bicyclo[4.3.0]nona-3,7-diene
3048-65-5

bicyclo[4.3.0]nona-3,7-diene

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
With tert-butylhydroquinone In diphenylether at 215℃; for 2.58333h; Product distribution / selectivity;94.19%
vanadocene

vanadocene

dibutyltin dibenzoate
5847-54-1

dibutyltin dibenzoate

A

tin
7440-31-5

tin

B

2C5H5(1-)*2V(3+)*4OCOC6H5(1-) = [(C5H5)V(OCOC6H5)2]2

2C5H5(1-)*2V(3+)*4OCOC6H5(1-) = [(C5H5)V(OCOC6H5)2]2

C

(Benzoyloxy)tributylstannan
4342-36-3

(Benzoyloxy)tributylstannan

D

dibutyltin
1191-48-6

dibutyltin

E

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In toluene molar ratio Cp2V/Sn-compound 1/2, sealed ampoule, 20°C, 24 h;A n/a
B 94%
C n/a
D n/a
E 84%
(η-cyclopentadienyl)(η-cyclopentadiene)nickel tetrafluoroborate
84651-76-3

(η-cyclopentadienyl)(η-cyclopentadiene)nickel tetrafluoroborate

1-diphenylarsino-2-diphenylphosphinoethane
23582-06-1

1-diphenylarsino-2-diphenylphosphinoethane

A

cyclopentadienylnickel(diphenylphosphino(diphenylarsino)ethylidene)
85412-97-1

cyclopentadienylnickel(diphenylphosphino(diphenylarsino)ethylidene)

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In chloroform under Ar, Ni complex and ligand stirred in CHCl3 for 5 min; filtered, filtrate dropped in ether, filtered, dried in vac., elem. anal.;A 93%
B n/a
(S)-2-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-3-phenyl-propionic acid methyl ester
211567-40-7

(S)-2-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-3-phenyl-propionic acid methyl ester

A

N-methyl-L-phenylalanine methyl ester
2439-60-3, 27442-39-3

N-methyl-L-phenylalanine methyl ester

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In chloroform for 20h; Ambient temperature;A 92%
B n/a
(1R,4S,4aR,8aS)-1,4,5,6,7,8-Hexahydro-1,4-methano-naphthalene-4a,8a-dicarboxylic acid dimethyl ester

(1R,4S,4aR,8aS)-1,4,5,6,7,8-Hexahydro-1,4-methano-naphthalene-4a,8a-dicarboxylic acid dimethyl ester

A

1,2-dimethyl cyclohex-1-ene-1,2-dicarboxylate
4336-19-0

1,2-dimethyl cyclohex-1-ene-1,2-dicarboxylate

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In gas at 650℃;A 92%
B n/a
(η-cyclopentadienyl)(η-cyclopentadiene)nickel tetrafluoroborate
84651-76-3

(η-cyclopentadienyl)(η-cyclopentadiene)nickel tetrafluoroborate

2,4-dichloro-1,3-di-tert-butyl-1,3,2,4-diazadiphosphetidine
24335-35-1

2,4-dichloro-1,3-di-tert-butyl-1,3,2,4-diazadiphosphetidine

A

[(C5H5)Ni(P2Cl2(NC(CH3)3)2)2](1+)*BF4(1-)=[(C5H5)Ni(P2Cl2(NC(CH3)3)2)2]BF4
85413-22-5

[(C5H5)Ni(P2Cl2(NC(CH3)3)2)2](1+)*BF4(1-)=[(C5H5)Ni(P2Cl2(NC(CH3)3)2)2]BF4

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In chloroform under Ar, nickel complex and CHCl3 soln. of ligand (molar ratio 1:2) stirred at 0°C for 1 h; filtered, filtrate mixed with ether, decanted, washed with ether until solidification, dried in vac., elem. anal.;A 92%
B n/a
Tricyclo<5.2.1.02.6>deca-3,8-dien
247936-95-4

Tricyclo<5.2.1.02.6>deca-3,8-dien

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
at 0 - 20℃; under 50 - 100 Torr; Temperature; Inert atmosphere; Large scale;91.7%
at 158.5 - 220.7℃; Kinetics; Rate constant; Thermodynamic data; activation parameters: Ea, ΔH, ΔS;
at 160 - 170℃;
C16H20O4
132785-65-0

C16H20O4

A

2,2-Dimethyl-cyclopenta-3,5-diene-1,3-dicarboxylic acid dimethyl ester
132785-67-2

2,2-Dimethyl-cyclopenta-3,5-diene-1,3-dicarboxylic acid dimethyl ester

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In neat (no solvent) at 160℃;A n/a
B 91%
In neat (no solvent) at 160℃;A 91%
B n/a
1-((1S,3R,7R)-4,4-Dioxo-4λ6-thia-tricyclo[5.2.1.02,6]dec-8-en-3-yl)-pentan-1-one
93469-35-3

1-((1S,3R,7R)-4,4-Dioxo-4λ6-thia-tricyclo[5.2.1.02,6]dec-8-en-3-yl)-pentan-1-one

A

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

B

trans-1,3-nonadien-5-one
83339-20-2

trans-1,3-nonadien-5-one

Conditions
ConditionsYield
at 650℃; under 0.01 Torr;A n/a
B 91%
(S)-2-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-4-methyl-pentanoic acid methyl ester
112018-28-7, 112018-29-8, 126574-84-3

(S)-2-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-4-methyl-pentanoic acid methyl ester

trifluoroacetic acid
76-05-1

trifluoroacetic acid

A

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

B

dimethylleucine trifluoroacetate
111934-20-4

dimethylleucine trifluoroacetate

Conditions
ConditionsYield
With triethylsilane In chloroform for 20h; Ambient temperature;A n/a
B 91%
8-quinolinol
148-24-3

8-quinolinol

tris(cyclopentadienyl)ytterbium(III)

tris(cyclopentadienyl)ytterbium(III)

A

dicyclopentadienylytterbium 8-quinolinolate

dicyclopentadienylytterbium 8-quinolinolate

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In tetrahydrofuran Addn. of Yb-complex soln to soln. of 8-hydroxyquinoline under Ar, stirring 24 h at room temp.; Concg., addn. of n-hexane pptd. a solid, washing (n-hexane), crystn. (THF/n-hexane), elem. anal.;A 91%
B n/a
(1S,3S,7R)-3-Pentyl-4-thia-tricyclo[5.2.1.02,6]dec-8-ene 4,4-dioxide
83927-51-9

(1S,3S,7R)-3-Pentyl-4-thia-tricyclo[5.2.1.02,6]dec-8-ene 4,4-dioxide

A

(E)-1,3-nonadiene
77192-27-9

(E)-1,3-nonadiene

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
at 650℃; under 0.01 Torr;A 90%
B n/a
at 650℃; Yields of byproduct given;
2-(5-Norbornen-2-yl)imidazol
91937-77-8

2-(5-Norbornen-2-yl)imidazol

A

2-vinyl imidazole
43129-93-7

2-vinyl imidazole

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
With 4-methoxy-phenol In methanol at 500℃;A 90%
B n/a
((1S,3R,7R)-4,4-Dioxo-4λ6-thia-tricyclo[5.2.1.02,6]dec-8-en-3-yl)-trimethyl-silane
86593-81-9

((1S,3R,7R)-4,4-Dioxo-4λ6-thia-tricyclo[5.2.1.02,6]dec-8-en-3-yl)-trimethyl-silane

A

(E)-1-(trimethylsilyl)buta-1,3-diene
71504-26-2

(E)-1-(trimethylsilyl)buta-1,3-diene

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
at 650℃; under 0.01 Torr;A 89%
B n/a
vanadocene

vanadocene

tributyltin acetate
56-36-0

tributyltin acetate

A

{(η5-cyclopentadienyl)vanadium diacetate}2

{(η5-cyclopentadienyl)vanadium diacetate}2

B

bis(tri-n-butyltin)
813-19-4

bis(tri-n-butyltin)

C

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In neat (no solvent) molar ratio Cp2V/Sn-compound 1/2, sealed ampoule, 120°C, 16 h; elem. anal.;A 89%
B 10.07%
C 58.5%
(S)-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-phenyl-acetic acid methyl ester
111934-15-7, 112018-33-4, 112458-30-7, 112458-34-1

(S)-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-phenyl-acetic acid methyl ester

A

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

B

methyl (2S)-(methylamino)(phenyl)acetate
111934-22-6

methyl (2S)-(methylamino)(phenyl)acetate

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In chloroform for 20h; Ambient temperature;A n/a
B 88%
3-benzoyl-2-oxa-3-azabicyclo<2.2.1>hept-5-ene
59438-62-9

3-benzoyl-2-oxa-3-azabicyclo<2.2.1>hept-5-ene

benzylamine
100-46-9

benzylamine

A

N-benzylbenzamide
1485-70-7

N-benzylbenzamide

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In toluene at 80℃; for 20h; Product distribution; Mechanism; var. amine; determination of formed N2O; retro-Diels Alder dissociation;A 88%
B n/a
(η-cyclopentadienyl)(η-cyclopentadiene)nickel tetrafluoroborate
84651-76-3

(η-cyclopentadienyl)(η-cyclopentadiene)nickel tetrafluoroborate

trimethylantimony
594-10-5

trimethylantimony

A

[Ni(C5H5)(Sb(CH3)3)2](1+)*BF4(1-)=[Ni(C5H5)(Sb(CH3)3)2]BF4
85836-32-4

[Ni(C5H5)(Sb(CH3)3)2](1+)*BF4(1-)=[Ni(C5H5)(Sb(CH3)3)2]BF4

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In diethyl ether under Ar, Ni complex in ether mixed with stibane ligand (molar ratio 1:2), stirred for 5 h at room temp.; filtered, washed with ether, dried in vac., elem. anal.;A 88%
B n/a
tris(cyclopentadienyl)ytterbium(III)

tris(cyclopentadienyl)ytterbium(III)

2-amino-phenol
95-55-6

2-amino-phenol

A

dicyclopentadienylytterbium o-aminophenolate

dicyclopentadienylytterbium o-aminophenolate

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In tetrahydrofuran Addn. of Yb-complex soln to soln. of o-aminophenol under Ar, stirring 24 h at room temp.; Concg., addn. of n-hexane pptd. a solid, washing (n-hexane), crystn. (THF/n-hexane), elem. anal.;A 87%
B n/a
8-quinolinol
148-24-3

8-quinolinol

tris(cyclopentadienyl)neodymium(III)
1080547-39-2

tris(cyclopentadienyl)neodymium(III)

A

dicyclopentadienylneodymium 8-quinolinolate

dicyclopentadienylneodymium 8-quinolinolate

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In tetrahydrofuran Addn. of Nd-complex soln to soln. of 8-hydroxyquinoline under Ar, stirring 24 h at room temp.; Concg., addn. of n-hexane pptd. a solid, washing (n-hexane), crystn. (THF/n-hexane), elem. anal.;A 87%
B n/a
[Ni(C5H5)(Sb(C6H5)3)2](1+)*BF4(1-)=[Ni(C5H5)(Sb(C6H5)3)2]BF4
85836-36-8

[Ni(C5H5)(Sb(C6H5)3)2](1+)*BF4(1-)=[Ni(C5H5)(Sb(C6H5)3)2]BF4

bis(diphenylstibino)methane
30224-53-4

bis(diphenylstibino)methane

A

[Ni(C5H5)(Sb(C6H5)2CH2Sb(C6H5)2)2](1+)*BF4(1-)=[Ni(C5H5)(Sb(C6H5)2CH2Sb(C6H5)2)2]BF4
85836-38-0

[Ni(C5H5)(Sb(C6H5)2CH2Sb(C6H5)2)2](1+)*BF4(1-)=[Ni(C5H5)(Sb(C6H5)2CH2Sb(C6H5)2)2]BF4

B

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In chloroform under Ar, Ni complex in CHCl3 mixed at 0°C with stibane ligand (molar ratio 1:2), stirred for 10 min; filtered, to filtrate added ether, solid washed with ether, dried in vac., elem. anal.;A 87%
B n/a
cyclohexanone
108-94-1

cyclohexanone

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

cyclopenta-2,4-dien-1-ylidenecyclohexane
3141-04-6

cyclopenta-2,4-dien-1-ylidenecyclohexane

Conditions
ConditionsYield
Stage #1: cyclohexanone; cyclopenta-1,3-diene With pyrrolidine In methanol at 20℃; Inert atmosphere;
Stage #2: With acetic acid In methanol for 0.15h;
100%
In methanol for 0.416667h; Ambient temperature; new method;96%
With pyrrolidine In methanol for 0.416667h; Ambient temperature;96%
fumaryl dichloride
627-63-4

fumaryl dichloride

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

endo,exo-bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid dichloride
4582-21-2

endo,exo-bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid dichloride

Conditions
ConditionsYield
In toluene Heating;100%
With diethyl ether
In diethyl ether
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

(1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester
2903-75-5

(1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
In water Ambient temperature;100%
With 3-phenyl-propenal; bromocatecholborane In dichloromethane at -78℃; for 3h;98%
With [BCl2(1-methylimidazole)][Al2Cl7] In neat (no solvent) at 0℃; for 0.0833333h; Diels-Alder Cycloaddition; Inert atmosphere;93%
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

norbornene-5,6-dicarboxylic acid
1200-88-0

norbornene-5,6-dicarboxylic acid

Conditions
ConditionsYield
In water; acetone at 50℃; for 24h; Diels-Alder Cycloaddition;100%
In 1,4-dioxane at 60℃; for 1h;94%
With N,N-dimethyl-formamide andere polare Loesungsmittel;
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

acetone
67-64-1

acetone

6,6'-dimethyl fulvene
2175-91-9

6,6'-dimethyl fulvene

Conditions
ConditionsYield
Stage #1: cyclopenta-1,3-diene; acetone With pyrrolidine In methanol at 20℃; Inert atmosphere;
Stage #2: With acetic acid In methanol for 0.15h;
100%
With pyrrolidine In methanol at -10 - 20℃; for 1h; Inert atmosphere;100%
With methylamine for 4.5h;92%
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

p-benzoquinone
106-51-4

p-benzoquinone

norbornenoquinone
51175-59-8

norbornenoquinone

Conditions
ConditionsYield
In hexane; ethyl acetate at 0℃; for 3.5h; Diels-Alder Cycloaddition;100%
In methanol at -78 - 0℃; Inert atmosphere; optical yield given as %de;98%
In hexane; ethyl acetate at 0℃; for 4h; Diels-Alder reaction;97%
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

Acetylenedicarboxylic acid
142-45-0

Acetylenedicarboxylic acid

bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid
15872-28-3

bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid

Conditions
ConditionsYield
In 1,4-dioxane at 20℃; for 12h; Diels-Alder cycloaddition;100%
In diethyl ether Ambient temperature;85%
Stage #1: Acetylenedicarboxylic acid With (2-bromophenyl)boronic acid In dichloromethane at 25℃; for 0.166667h; Inert atmosphere;
Stage #2: cyclopenta-1,3-diene In dichloromethane at 25℃; for 48h; Diels-Alder cycloaddition; Inert atmosphere;
84%
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

diethyl 2,3-diazanorbornene-2,3-dicarboxylate
14011-60-0

diethyl 2,3-diazanorbornene-2,3-dicarboxylate

Conditions
ConditionsYield
In dichloromethane at 0℃;100%
In diethyl ether at 0℃; for 12h;100%
In diethyl ether; toluene at 20℃; for 21.5h; Reflux;55%
With diethyl ether
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

1,2-Dicyanoethylene
764-42-1

1,2-Dicyanoethylene

bicyclo<2.2.1>hept-5,6-ene-2α,3β-dicarbonitrile
6343-16-4, 24425-58-9, 38447-89-1, 51252-31-4

bicyclo<2.2.1>hept-5,6-ene-2α,3β-dicarbonitrile

Conditions
ConditionsYield
In methanol at 0 - 20℃; Diels-Alder reaction;100%
In methanol at 0℃; for 1h; Diels-Alder Cycloaddition;99%
In 1,4-dioxane for 6h; Ambient temperature;93%
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

endo-Dicyclopentadien
1755-01-7

endo-Dicyclopentadien

Conditions
ConditionsYield
In cyclohexane at 119.84℃; for 2h; Diels-Alder Cycloaddition;100%
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

acrolein
107-02-8

acrolein

(+/-)-endo-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde
19926-90-0

(+/-)-endo-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde

Conditions
ConditionsYield
With trityl tetrafluoroborate In dichloromethane at 20℃; for 16h; Diels-Alder Cycloaddition;100%
With methyltrioxorhenium(VII) In chloroform for 1h; Ambient temperature;90%
With 1-ethyl-3-methyl-1H-imidazol-3-ium chloride at 20℃; for 0.166667h; Diels-Alder reaction;88%
maleic anhydride
108-31-6

maleic anhydride

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With 3-(n-butoxycarbonyl)-1-methylpyridinium bis(trifluoromethanesulfonyl)imide at 20℃; for 0.166667h; Diels-Alder reaction; diastereoselective reaction;100%
With 1-hexyl-3-methylimidazolium tetrafluoroborate; K-10 montmorillonite at 20℃; for 0.0833333h; Diels-Alder reaction;99%
In dichloromethane at 0 - 20℃; for 10h; Diels-Alder Cycloaddition; Inert atmosphere;98%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

N-phenylbicyclo[2.2.1]hept-5-ene-2-endo,3-endo-dicarboximide
26234-46-8, 29377-36-4, 56552-68-2

N-phenylbicyclo[2.2.1]hept-5-ene-2-endo,3-endo-dicarboximide

Conditions
ConditionsYield
In neat (no solvent) at 20℃; for 0.0166667h; Diels-Alder Cycloaddition;100%
With 1-hexyl-3-methylimidazolium tetrafluoroborate; K-10 montmorillonite at 20℃; for 0.0833333h; Diels-Alder reaction;99%
With 3-(n-butoxycarbonyl)-1-methylpyridinium bis(trifluoromethanesulfonyl)imide at 20℃; for 0.166667h; Diels-Alder reaction; diastereoselective reaction;97%
1,3-diacetyl-2,3-dihydro-1H-imidazol-2-one
20212-13-9

1,3-diacetyl-2,3-dihydro-1H-imidazol-2-one

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(3aα,4α,7α,7aα)-1,3-diacetyl-1,3,3a,4,7,7a-hexahydro-4,7-methano-2H-benzimidazol-2-one
78932-02-2

(3aα,4α,7α,7aα)-1,3-diacetyl-1,3,3a,4,7,7a-hexahydro-4,7-methano-2H-benzimidazol-2-one

Conditions
ConditionsYield
at 140℃; for 24h; Diels-Alder reaction;100%
at 140℃; for 24h; Diels-Alder Cycloaddition; Sealed tube;98.6%
In xylene at 180℃; selaed tube;69%
formaldehyd
50-00-0

formaldehyd

benzylamine hydrochloride
3287-99-8, 39110-74-2

benzylamine hydrochloride

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

N-benzyl-2-azanorborn-5-ene
112375-05-0

N-benzyl-2-azanorborn-5-ene

Conditions
ConditionsYield
In water100%
In water at 20℃; for 3h;73%
In water for 3h; Ambient temperature; Yield given;
In water for 16h; Ambient temperature;6.69 g
In water at 20℃; for 3h;
1-(chloromethyl)maleic anhydride
41702-49-2

1-(chloromethyl)maleic anhydride

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(1S,2S,6S,7R)-2-Chloromethyl-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
143668-21-7

(1S,2S,6S,7R)-2-Chloromethyl-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions
ConditionsYield
In diethyl ether 1) 0.5 h, reflux, 2) RT, 3 h;100%
2,3-Dimethoxy-5-methyl-1,4-benzoquinone
605-94-7

2,3-Dimethoxy-5-methyl-1,4-benzoquinone

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

4,5-dimethoxy-2-methyltricyclo<6.2.1.02,7>undeca-4,9-diene-3,6-dione

4,5-dimethoxy-2-methyltricyclo<6.2.1.02,7>undeca-4,9-diene-3,6-dione

Conditions
ConditionsYield
In dichloromethane for 96h; Ambient temperature;100%
4-oxopent-2-ynoic acid methyl ester
41726-06-1

4-oxopent-2-ynoic acid methyl ester

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

3-Acetyl-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid methyl ester
148042-65-3

3-Acetyl-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
In dichloromethane for 18h;100%
trifluoromethyldiiodophosphine
421-59-0

trifluoromethyldiiodophosphine

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

2,3-Bis-trifluoromethyl-2,3-diphospha-bicyclo[2.2.1]hept-5-ene
104927-58-4

2,3-Bis-trifluoromethyl-2,3-diphospha-bicyclo[2.2.1]hept-5-ene

Conditions
ConditionsYield
With tin(ll) chloride In tetrahydrofuran100%
1,1-bis(trichlorosilyl)ethylene
684-18-4

1,1-bis(trichlorosilyl)ethylene

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

5,5-Bis-trichlorosilanyl-bicyclo[2.2.1]hept-2-ene
120852-93-9

5,5-Bis-trichlorosilanyl-bicyclo[2.2.1]hept-2-ene

Conditions
ConditionsYield
at 60 - 70℃; for 3h;100%
5-hydroxynaphtho-1,4-quinone
481-39-0

5-hydroxynaphtho-1,4-quinone

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(1R*,4S*,4aR*,9aS*)-1,4,4a,9a-tetrahydro-5-hydroxy-1,4-methano-9,10-anthracenedione
163180-66-3

(1R*,4S*,4aR*,9aS*)-1,4,4a,9a-tetrahydro-5-hydroxy-1,4-methano-9,10-anthracenedione

Conditions
ConditionsYield
In chloroform for 0.5h; Ambient temperature;100%
In propan-1-ol at 25℃; Thermodynamic data; Rate constant; other solvents and their mixture with water; isobaric activation parameters;
In dichloromethane at 20℃; Reflux;
di-tert-butyl-diazodicarboxylate
870-50-8

di-tert-butyl-diazodicarboxylate

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate
39203-22-0

di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Conditions
ConditionsYield
In dichloromethane at 0℃;100%
In diethyl ether for 48h; Ambient temperature;94%
In dichloromethane Inert atmosphere;89%
In dichloromethane89%
In diethyl ether at 0℃; for 12h;
styrylphosphonic acid
1707-08-0

styrylphosphonic acid

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(3-phenylbicyclo<2.2.1>hept-5-en-2-yl)phosphonic acid

(3-phenylbicyclo<2.2.1>hept-5-en-2-yl)phosphonic acid

Conditions
ConditionsYield
In diethyl ether for 72h; Ambient temperature;100%
In diethyl ether at 20℃; for 48h;91.5%
2-benzylcyclohexa-2,5-diene-1,4-dione
38940-10-2

2-benzylcyclohexa-2,5-diene-1,4-dione

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

rel-(1S,4R,4aS,8aR)-6-benzyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione
100848-86-0, 117893-87-5

rel-(1S,4R,4aS,8aR)-6-benzyl-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione

Conditions
ConditionsYield
for 0.416667h; Ambient temperature;100%
In methanol at 25℃; Diels-Alder reaction;82%
2,3-dichloro-1,4-benzoquinone
5145-42-6

2,3-dichloro-1,4-benzoquinone

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

4,5-dichlorotricyclo<6.2.1.02,7>undeca-4,9-diene-3,6-dione
82253-62-1

4,5-dichlorotricyclo<6.2.1.02,7>undeca-4,9-diene-3,6-dione

Conditions
ConditionsYield
In diethyl ether at 20℃; for 5h; Diels-Alder reaction;100%
In benzene Yield given;
In benzene Diels-Alder Cycloaddition;
1,2-dichloro-1,2-dicyanoethylene
85278-93-9

1,2-dichloro-1,2-dicyanoethylene

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

2,3-Dichloro-bicyclo[2.2.1]hept-5-ene-2,3-dicarbonitrile
86165-09-5

2,3-Dichloro-bicyclo[2.2.1]hept-5-ene-2,3-dicarbonitrile

Conditions
ConditionsYield
In dichloromethane at 25℃; for 72h;100%
2,3-Dichloro-5-methyl-2,5-cyclohexadiene-1,4-dione
30685-19-9

2,3-Dichloro-5-methyl-2,5-cyclohexadiene-1,4-dione

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(1α,4α,4aβ,8aβ)-6,7-Dichloro-1,4,4a,8a-tetrahydro-4a-methyl-1,4-methanonaphthalene-5,8-dione

(1α,4α,4aβ,8aβ)-6,7-Dichloro-1,4,4a,8a-tetrahydro-4a-methyl-1,4-methanonaphthalene-5,8-dione

Conditions
ConditionsYield
In methanol for 2h;100%
Oxo-(4-phenylazo-phenylamino)-dithioacetic acid methyl ester
104688-95-1

Oxo-(4-phenylazo-phenylamino)-dithioacetic acid methyl ester

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(1R,4S)-3-Methylsulfanyl-2-thia-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid (4-phenylazo-phenyl)-amide
110968-47-3

(1R,4S)-3-Methylsulfanyl-2-thia-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid (4-phenylazo-phenyl)-amide

Conditions
ConditionsYield
In chloroform Heating;100%

Cyclopentadiene Consensus Reports

Reported in EPA TSCA Inventory.

Cyclopentadiene Standards and Recommendations

OSHA PEL: TWA 75 ppm
ACGIH TLV: TWA 75 ppm
DFG MAK: 75 ppm (210 mg/m3)

Cyclopentadiene Analytical Methods

For occupational chemical analysis use NIOSH: 1,3-Cyclopentadiene, 2523.

Cyclopentadiene Specification

 The Cyclopentadiene, with the CAS registry number 542-92-7,is also known as 1,3-Cyclopentadiene. It belongs to the product categories of Organic matters. This chemical's molecular formula is C5H6 and molecular weight is 66.10.Its EINECS number is 542-92-7. What's more,Its systematic name is Cyclopentadiene.It is a colourless liquid which is stable at room temperature and incompatible with oxidizing agents, acids and a wide variety of other compounds.It may form peroxides in storage.And it may undergo spontaneous polymerisation. It Decomposes on heating,mixtures with air are explosive.It is used for organic synthetic intermediates, and manufacturing pesticides.In addition, it is mainly used for resin industry, synthetic rubber, etc.

Physical properties about Cyclopentadiene are:
(1)ACD/LogP:  2.087; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  2.09; (4)ACD/LogD (pH 7.4):  2.09; (5)ACD/BCF (pH 5.5):  22.72; (6)ACD/BCF (pH 7.4):  22.72; (7)ACD/KOC (pH 5.5):  325.50; (8)ACD/KOC (pH 7.4):  325.50; (9)#H bond acceptors:  0; (10)#H bond donors:  0; (11)#Freely Rotating Bonds:  0; (12)Index of Refraction:  1.503; (13)Molar Refractivity:  22.266 cm3; (14)Molar Volume:  75.303 cm3; (15)Surface Tension:  34.859001159668 dyne/cm; (16)Density:  0.878 g/cm3; (17)Flash Point:  -32.166 °C; (18)Enthalpy of Vaporization:  27.4 kJ/mol; (19)Boiling Point:  41.499 °C at 760 mmHg; (20)Vapour Pressure:  418.459991455078 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:C1C=CC=C1;
(2)Std. InChI:InChI=1S/C5H6/c1-2-4-5-3-1/h1-4H,5H2 ;
(3)Std. InChIKey:ZSWFCLXCOIISFI-UHFFFAOYSA-N.

The toxicity data of Cyclopentadiene as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation 14gm/m3 (14000mg/m3) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: AGGRESSION

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 9(12), Pg. 13, 1965.
mouse LD50 oral 800mg/kg (800mg/kg)   Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 9, Pg. 27, 1967.
rabbit LD50 skin 430mg/kg (430mg/kg)   National Technical Information Service. Vol. OTS0535718,
rat LC50 inhalation 39gm/m3 (39000mg/m3) BEHAVIORAL: AGGRESSION

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: EXCITEMENT
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 9(12), Pg. 13, 1965.
rat LD50 oral 113mg/kg (113mg/kg)   National Technical Information Service. Vol. OTS0535718,

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