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Merck
CN

304026

Sodium cyclopentadienylide

2.4 M in THF, liquid

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
NACRES:
NA.22
PubChem Substance ID:
24858317
UNSPSC Code:
12161600
MDL number:
MFCD00012161
Beilstein/REAXYS Number:
969542

Key Documents

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Product Name

Sodium cyclopentadienylide, 2.4 M in THF

InChI

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

SMILES string

[Na]C1C=CC=C1

InChI key

PDTZVKVFAJGNRV-UHFFFAOYSA-N

form

liquid

reaction suitability

reagent type: ligand

concentration

2.4 M in THF

density

0.938 g/mL at 25 °C

Quality Level

100

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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.

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Danger

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3 - Water-react 1

target_organs

Central nervous system, Respiratory system

supp_hazards

EUH018,EUH019

Storage Class

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

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBS1695
SHBR3162
SHBQ6437
SHBP6345
SHBP6349

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Journal of Organometallic Chemistry, 467, 75-75 (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 the Chemical Society. Chemical Communications, 2007-2007 (1994)
Journal of Organometallic Chemistry, 691, 5831-5831 (2006)
Palladium-catalyzed asymmetric allylic substitution with a cyclopentadienide: asymmetric synthesis of metallocenes.
Suzuka T, et al.
Tetrahedron Asymmetry, 14(4), 511-515 (2003)
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