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Name	Sodium cyclopentadienylide	EINECS	225-636-8
CAS No.	4984-82-1	Density	0.946 g/mL at 20 °C
PSA	0.00000	LogP	1.45020
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		Hazard Symbols	Xi,F
Synonyms	Sodium,cyclopentadienyl- (6CI,7CI);2,4-Cyclopentadien-1-yl sodium;Cyclopentadienylsodium;Sodium cyclopentadienide;Sodium cyclopentadienylide;

Sodium cyclopentadienylide Synthetic route

: bis(η3-allyl-μ-chloropalladium(II))

: 4984-82-1
sodium cyclopentadienylide

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

Conditions

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

: C12H17ClSi

: 4984-82-1
sodium cyclopentadienylide

: C17H22Si

Conditions

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

: C11H16ClNSi

: 4984-82-1
sodium cyclopentadienylide

: C16H21NSi

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;	99%

: 112070-18-5
the dicamphorsulfonate of (1S,2S,4S,5S)-2,5-diphenylcyclohexane-1,4-diol

: 4984-82-1
sodium cyclopentadienylide

: C23H22

Conditions

Conditions	Yield
With sodium hydride In 1,2-dimethoxyethane 1.) 0 deg C, 2.5 h; 2.) reflux, 4 h;	98%

: 109-72-8, 29786-93-4
n-butyllithium

: 6591-26-0
bis(trimethylsilyl)aminodichloroborane

: 4984-82-1
sodium cyclopentadienylide

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

Conditions

Conditions	Yield
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%

: 29442-43-1
1‐phenyl‐1‐chloro‐1‐silacyclohexane

: 4984-82-1
sodium cyclopentadienylide

: C16H20Si

Conditions

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

: C10H14ClNSi

: 4984-82-1
sodium cyclopentadienylide

: C15H19NSi

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; for 3h; Inert atmosphere;	98%

: phenylmenthyl methanesulfonate

: 4984-82-1
sodium cyclopentadienylide

: ((-)-phenylmenthylcyclopentadienyl)lithium

Conditions

Conditions	Yield
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

: 4984-82-1
sodium cyclopentadienylide

: C14H17NSi

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;	97%

: 21959-01-3, 125410-70-0, 125410-71-1
zirconium tetrachloride bis(tetrahydrofuran) complex

: 6591-26-0
bis(trimethylsilyl)aminodichloroborane

: 4984-82-1
sodium cyclopentadienylide

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

Conditions

Conditions	Yield
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%

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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