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304026

Sigma-Aldrich

Sodium cyclopentadienylide

2.4 M in THF

Synonym(s):

Cyclopentadienylsodium solution

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About This Item

Empirical Formula (Hill Notation):
C5H5Na
CAS Number:
4984-82-1
Molecular Weight:
88.08
Beilstein:
969542
MDL number:
MFCD00012161
UNSPSC Code:
12352300
PubChem Substance ID:
24858317
NACRES:
NA.22

form

liquid

Quality Level

100

reaction suitability

reagent type: ligand

concentration

2.4 M in THF

density

0.938 g/mL at 25 °C

SMILES string

[Na]C1C=CC=C1

InChI

1S/C5H5.Na/c1-2-4-5-3-1;/h1-5H;

InChI key

PDTZVKVFAJGNRV-UHFFFAOYSA-N

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Application

It can also be used in the synthesis of:
  • Ruthenocene and fullerene molecular hybrid, Ru(η5- C60Me5)( η5-C5H5) (bucky ruthenocene).
  • Allyl-substituted cyclopentadiene by palladium-catalyzed allylic alkylation.
  • Bis(cyclopentadienyl)zirconium dichloride which is used as a catalyst in the synthesis of bis(indolyl)methanes and alkylation of heteroaryls.
  • Cp-cobaltacycles from diphenylphosphinoalkynes and CoCl(PPh3)3.
Sodium cyclopentadienylide is a useful reagent for the preparation of metallocenes and cyclopentadienyl metal complexes.

Signal Word

Danger

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - Water-react 1

Supplementary Hazards

EUH018 - EUH019

Storage Class Code

4.3 - Hazardous materials, which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Palladium-catalyzed asymmetric allylic substitution with a cyclopentadienide: asymmetric synthesis of metallocenes.
Suzuka T, et al.
Tetrahedron Asymmetry, 14(4), 511-515 (2003)
Journal of the Chemical Society. Chemical Communications, 2007-2007 (1994)
Bis (cyclopentadienyl) zirconium dichloride for alkylation of heteroaromatics and synthesis of bis (indolyl) methanes.
Kantam ML, et al.
Catalysis Letters, 98(2-3), 117-121 (2004)
Journal of Organometallic Chemistry, 467, 75-75 (1994)
Synthesis and reactivity of bucky ruthenocene Ru(η5- C60Me5)( η5-C5H5).
Matsuo Y, et al.
Chemistry Letters (Jpn), 33(1), 68-69 (2003)
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