Product Name

  • Name

    SODIUM CYCLOPENTADIENIDE

  • EINECS 225-636-8
  • CAS No. 4984-82-1
  • Density 0.946 g/mL at 20 °C
  • Solubility Reacts with water.
  • Melting Point 172 °C
  • Formula C5H5Na
  • Boiling Point 41.5ºC at 760mmHg
  • Molecular Weight 88.0845
  • Flash Point 1 °F
  • Transport Information UN 1993
  • Appearance white to greyish or yellowish powder
  • Safety 16-26-36/37/39-45
  • Risk Codes 11-19-34
  • Molecular Structure Molecular Structure of 4984-82-1 (SODIUM CYCLOPENTADIENIDE)
  • Hazard Symbols IrritantXi,FlammableF
  • Synonyms Sodium,cyclopentadienyl- (6CI,7CI);2,4-Cyclopentadien-1-yl sodium;Cyclopentadienylsodium;Sodium cyclopentadienide;Sodium cyclopentadienylide;
  • PSA 0.00000
  • LogP 1.45020

Synthetic route

bis(η3-allyl-μ-chloropalladium(II))

bis(η3-allyl-μ-chloropalladium(II))

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

allyl(cyclopentadiene)palladium(II)
1271-03-0

allyl(cyclopentadiene)palladium(II)

Conditions
ConditionsYield
In tetrahydrofuran; benzene at -20 - 20℃; for 1.5h; Inert atmosphere; Schlenk technique;99%
C12H17ClSi

C12H17ClSi

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

C17H22Si

C17H22Si

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 5h; Inert atmosphere;99%
C11H16ClNSi

C11H16ClNSi

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

C16H21NSi

C16H21NSi

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;99%
the dicamphorsulfonate of (1S,2S,4S,5S)-2,5-diphenylcyclohexane-1,4-diol
112070-18-5

the dicamphorsulfonate of (1S,2S,4S,5S)-2,5-diphenylcyclohexane-1,4-diol

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

C23H22

C23H22

Conditions
ConditionsYield
With sodium hydride In 1,2-dimethoxyethane 1.) 0 deg C, 2.5 h; 2.) reflux, 4 h;98%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

bis(trimethylsilyl)aminodichloroborane
6591-26-0

bis(trimethylsilyl)aminodichloroborane

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

Li2[(cyclopentadiene)2BN(Si(CH3)3)2]

Li2[(cyclopentadiene)2BN(Si(CH3)3)2]

Conditions
ConditionsYield
In hexane N2 atmosphere, addn. of soln. of borane to suspension of sodium cyclopentadiene at room temp., stirring (room temp., 2 h), addn. of BuLi at 0°C, warming to room temp., stirring (1 h); removement of volatiles (high vacuum), extn. (hexane, overnight), filtration, drying (vacuum);98%
...Expand
1‐phenyl‐1‐chloro‐1‐silacyclohexane
29442-43-1

1‐phenyl‐1‐chloro‐1‐silacyclohexane

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

C16H20Si

C16H20Si

Conditions
ConditionsYield
In 2-methyltetrahydrofuran at 0℃; for 8h; Inert atmosphere;98%
C10H14ClNSi

C10H14ClNSi

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

C15H19NSi

C15H19NSi

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 3h; Inert atmosphere;98%
phenylmenthyl methanesulfonate

phenylmenthyl methanesulfonate

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

((-)-phenylmenthylcyclopentadienyl)lithium

((-)-phenylmenthylcyclopentadienyl)lithium

Conditions
ConditionsYield
Stage #1: phenylmenthyl methanesulfonate; sodium cyclopentadienylide In tetrahydrofuran for 12h; Heating;
Stage #2: With n-butyllithium In hexane; pentane at 20℃; for 12h; Further stages.;		97%
C9H12ClNSi

C9H12ClNSi

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

C14H17NSi

C14H17NSi

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;97%
zirconium tetrachloride bis(tetrahydrofuran) complex
21959-01-3, 125410-70-0, 125410-71-1

zirconium tetrachloride bis(tetrahydrofuran) complex

bis(trimethylsilyl)aminodichloroborane
6591-26-0

bis(trimethylsilyl)aminodichloroborane

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

[((CH3)3Si)2NB(η(5)-cyclopentadienyl)2]ZrCl2
253798-57-1

[((CH3)3Si)2NB(η(5)-cyclopentadienyl)2]ZrCl2

Conditions
ConditionsYield
With BuLi In diethyl ether; hexane N2 atm., (borane, NaCp (hexane, 0°C), warming to room temp., stirring (2 h), filtration, washing (Et2O), BuLi (hexane, 0°C), warming to room temp., stirring (16 h), Zr complex and Et2O (-70°C), warming to room temp, stirring (2 h); filtration, pptn. (-30°C); elem. anal.;96%
...Expand
1-chloro-1-phenyl-1-silacyclobutane
3401-28-3

1-chloro-1-phenyl-1-silacyclobutane

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

C14H16Si

C14H16Si

Conditions
ConditionsYield
In tetrahydrofuran at -20℃; for 3.5h; Inert atmosphere;96%
C10H14ClNSi

C10H14ClNSi

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

C15H19NSi

C15H19NSi

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 1.5h; Inert atmosphere;96%
bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]

bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

allyl(cyclopentadiene)palladium(II)
1271-03-0

allyl(cyclopentadiene)palladium(II)

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 20℃; Inert atmosphere;95%
C8H10ClNSi

C8H10ClNSi

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

C13H15NSi

C13H15NSi

Conditions
ConditionsYield
In tetrahydrofuran at -50 - -45℃; for 3h; Inert atmosphere;95%
1-chloro-1-phenylsilacyclopentane
7488-24-6

1-chloro-1-phenylsilacyclopentane

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

C15H18Si

C15H18Si

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 2.5h; Inert atmosphere;95%
C10H12Cl2O2Si

C10H12Cl2O2Si

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

C15H17ClO2Si

C15H17ClO2Si

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 6h; Inert atmosphere;93%
N,N,N',N'-tetramethylsuccinamide
7334-51-2

N,N,N',N'-tetramethylsuccinamide

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

4-cyclopenta-2,4-dienylidene-4-dimethylamino-N,N-dimethyl-butyramide
765310-16-5

4-cyclopenta-2,4-dienylidene-4-dimethylamino-N,N-dimethyl-butyramide

Conditions
ConditionsYield
Stage #1: N,N,N',N'-tetramethylsuccinamide With triethyloxonium fluoroborate In dichloromethane at -30 - 20℃;
Stage #2: sodium cyclopentadienylide In tetrahydrofuran at -40℃;		92%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

lithium trimethylsilylcyclopentadienylide

lithium trimethylsilylcyclopentadienylide

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; sodium cyclopentadienylide In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; Schlenk technique;
Stage #2: With n-butyllithium In hexane at 0℃; for 12h;		92%
zirconium tetrachloride bis(tetrahydrofuran) complex
21959-01-3, 125410-70-0, 125410-71-1

zirconium tetrachloride bis(tetrahydrofuran) complex

(dimethylamino)dibromoborane
7360-64-7

(dimethylamino)dibromoborane

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

[(CH3)2NB(η(5)-cyclopentadienyl)2]ZrCl2
253798-56-0

[(CH3)2NB(η(5)-cyclopentadienyl)2]ZrCl2

Conditions
ConditionsYield
With BuLi In diethyl ether; hexane byproducts: NaBr; N2 atm., (borane, NaCp (hexane, 0°C), warming to room temp., stirring (2 h), filtration, washing (Et2O), BuLi (hexane, 0°C), warming to room temp., stirring (16 h), Zr complex and Et2O (-70°C), warming to room temp, stirring (2 h); filtration, pptn. (-30°C); elem. anal.;91%
...Expand
tris(acetonitrile)tricarbonylmolybdenum(0)
15038-48-9, 17731-95-2

tris(acetonitrile)tricarbonylmolybdenum(0)

phosphoric acid
86119-84-8, 7664-38-2

phosphoric acid

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

hydrido(tricarbonyl)(cyclopentadienyl)molybdenum
12176-06-6

hydrido(tricarbonyl)(cyclopentadienyl)molybdenum

Conditions
ConditionsYield
Stage #1: tris(acetonitrile)tricarbonylmolybdenum(0); sodium cyclopentadienylide In tetrahydrofuran Inert atmosphere;
Stage #2: phosphoric acid In tetrahydrofuran; water Reagent/catalyst;		90%
...Expand
triethylsilyl chloride
994-30-9

triethylsilyl chloride

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

lithium triethylsilylcyclopentadienylide

lithium triethylsilylcyclopentadienylide

Conditions
ConditionsYield
Stage #1: triethylsilyl chloride; sodium cyclopentadienylide In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Schlenk technique;
Stage #2: With n-butyllithium In hexane at 0℃; for 12h;		90%
sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

calcium dicyclopentadienide

calcium dicyclopentadienide

Conditions
ConditionsYield
With calcium borohydride In tetrahydrofuran at 20℃; for 1h;89.7%
(2,7-di-tert-butyl-9H-fluoren-9-yl)chloro(dimethyl)silane
161853-49-2

(2,7-di-tert-butyl-9H-fluoren-9-yl)chloro(dimethyl)silane

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

Cyclopenta-2,4-dienyl-(2,7-di-tert-butyl-9H-fluoren-9-yl)-dimethyl-silane
161853-50-5

Cyclopenta-2,4-dienyl-(2,7-di-tert-butyl-9H-fluoren-9-yl)-dimethyl-silane

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide In diethyl ether for 4h;88%
2-Chloroethyl chloroformate
627-11-2

2-Chloroethyl chloroformate

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

2-Cyclopentadienylidene-1,3-dioxolane
67399-79-5

2-Cyclopentadienylidene-1,3-dioxolane

Conditions
ConditionsYield
In acetonitrile at 25℃; for 1h; Product distribution; influence of reagents ratio, solvent and base nature on the yield of reaction; further solvents, further bases;86%
In acetonitrile at 25℃; for 1h;86%
2,6-bis(chloromethyl)pyridine
3099-28-3

2,6-bis(chloromethyl)pyridine

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

2,6-bis(methylenecyclopentadienyl)pyridine disodium salt
136133-17-0

2,6-bis(methylenecyclopentadienyl)pyridine disodium salt

Conditions
ConditionsYield
In tetrahydrofuran85%
bis(trimethylsilyl)aminodichloroborane
6591-26-0

bis(trimethylsilyl)aminodichloroborane

hafnium tetrachloride
13499-05-3

hafnium tetrachloride

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

[((CH3)3Si)2NB(η(5)-cyclopentadienyl)2]HfCl2
253798-58-2

[((CH3)3Si)2NB(η(5)-cyclopentadienyl)2]HfCl2

Conditions
ConditionsYield
With BuLi In diethyl ether; hexane N2 atm., (borane, NaCp (hexane, 0°C), warming to room temp., stirring (2 h), filtration, washing (Et2O), BuLi (hexane, 0°C), warming to room temp., stirring (16 h), HfCl4 and Et2O (-70°C), warming to room temp, stirring (2 h); filtration, pptn. (-30°C); elem. anal.;85%
...Expand
(2-chloroethyl)dimethylamine hydrochloride
4584-46-7

(2-chloroethyl)dimethylamine hydrochloride

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

<2-(Dimethylamino)ethyl>cyclopentadien
147699-91-0

<2-(Dimethylamino)ethyl>cyclopentadien

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran for 4h; Heating;83%
Diethyl carbonate
105-58-8

Diethyl carbonate

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

sodium (ethoxycarbonyl)cyclopentadienide

sodium (ethoxycarbonyl)cyclopentadienide

Conditions
ConditionsYield
at 40 - 105℃; for 2.5h; Schlenk technique; Inert atmosphere;83%
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

(benzoylcyclopentadienyl)sodium

(benzoylcyclopentadienyl)sodium

Conditions
ConditionsYield
In tetrahydrofuran for 24h; Heating;82%
choro(fluoren-9-yl)diphenylsilane
73220-53-8

choro(fluoren-9-yl)diphenylsilane

sodium cyclopentadienylide
4984-82-1

sodium cyclopentadienylide

cyclopentadienyl(fluoren-9-yl)diphenylsilane
162289-97-6

cyclopentadienyl(fluoren-9-yl)diphenylsilane

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide In diethyl ether for 4h;82%

Sodium cyclopentadienylide Specification

The IUPAC name of Sodium cyclopentadienide is sodium cyclopenta-1,3-diene. With the CAS registry number 4984-82-1, it is also named as Sodium, 2,4-cyclopentadienide. The product's other registry numbers are 152846-23-6; 223905-48-4; 27081-05-6; 28260-50-6; 36683-96-2; 38785-12-5; 38841-18-8; 63936-05-0; 73500-89-7. Besides, it is white to greyish or yellowish powder, which should be stored in sealed, dark, ventilated and dry place at 2-8 °C. In addition, its molecular formula is C5H5Na and molecular weight is 88.08.

The other characteristics of this product can be summarized as: (1)H-Bond Donor: 0; (2)H-Bond Acceptor: 1; (3)Rotatable Bond Count: 0; (4)Exact Mass: 88.028895; (5)MonoIsotopic Mass: 88.028895; (6)Heavy Atom Count: 6; (7)Complexity: 23.1; (8)EINECS: 225-636-8; (9)Density: 0.946 g/mL at 20 °C; (10)Flash Point: 1 °F.

Preparation of Sodium cyclopentadienide: this chemical is commercially prepared by treating Cyclopentadiene with Sodium:
2 Na + 2 C5H6 → 2 NaC5H5 + H2

Uses of Sodium cyclopentadienide: this chemical is a common reagent used for the preparation of metallocenes, such as the preparation of Ferrocene and Zirconocene dichloride:
2 NaC5H5 + FeCl2 → Fe(C5H5)2 + 2 NaCl
ZrCl4(thf)2 + 2 NaCp → Cp2ZrCl2 + 2 NaCl + 2 THF

When you are using this chemical, please be cautious about it as the following: it is highly flammable that may cause burns. It also may form explosive peroxides. Please keep away from sources of ignition. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection. Moreover, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)SMILES: [Na]C/1/C=C\C=C\1
(2)InChI: InChI=1/C5H5.Na/c1-2-4-5-3-1;/h1-5H;/rC5H5Na/c6-5-3-1-2-4-5/h1-5H
(3)InChIKey: PDTZVKVFAJGNRV-KEYBYSSPAM
(4)Std. InChI: InChI=1S/C5H5.Na/c1-2-4-5-3-1;/h1-5H
(5)Std. InChIKey: PDTZVKVFAJGNRV-UHFFFAOYSA-N

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