4984-82-1

Basic information

• Product Name: SODIUM CYCLOPENTADIENIDE
• Synonyms: CYCLOPENTADIENYLSODIUM;SODIUM CYCLOPENTADIENIDE;SODIUM CYCLOPENTADIENYLIDE;NACP;Cyclopentadienylsodium solution;cyclopenta-2,4-dien-1-ylsodium;SODIUM CYCLOPENTADIENIDE, 2.0M SOLUTION IN TETRAHYDROFURAN;CYCLOPENTADIENYLSODIUM SOLUTION, ~2 M IN THF
• CAS NO: 4984-82-1
• Molecular Formula: C₅H₅Na
• Molecular Weight: 88.08
• EINECS: 225-636-8
• Product Categories: metallocene
• Mol File: 4984-82-1.mol

Chemical Properties

• Melting Point: 172 °C
• Boiling Point: 41.5ºC at 760mmHg
• Flash Point: 1 °F
• Appearance: dark red/
• Density: 0.946 g/mL at 20 °C
• Storage Temp.: 2-8°C
• Water Solubility: Reacts with water.
• Sensitive: Air & Moisture Sensitive
• BRN: 969542
• CAS DataBase Reference: SODIUM CYCLOPENTADIENIDE(CAS DataBase Reference)
• NIST Chemistry Reference: SODIUM CYCLOPENTADIENIDE(4984-82-1)
• EPA Substance Registry System: SODIUM CYCLOPENTADIENIDE(4984-82-1)

Safety Data

• Hazard Codes: F,Xi,C
• Statements: 11-19-34-40-37-14/15
• Safety Statements: 16-26-36/37/39-45-43
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• F: 1-10
• TSCA: Yes
• HazardClass: 4.3
• PackingGroup: II
• Hazardous Substances Data: 4984-82-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Sodium cyclopentadienide is used as a reagent for the preparation of metallocenes, which are a class of organometallic compounds consisting of a metal atom bonded to one or more cyclopentadienyl (Cp) ligands. These compounds have a wide range of applications in various industries, including pharmaceuticals, materials science, and catalysis.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, sodium cyclopentadienide is used to prepare Cp-cobaltacycles from diphenylphosphinoalkynes and CoCl(PPh3)3. These Cp-cobaltacycles have potential applications in the development of new drugs and therapeutic agents, as they can exhibit unique biological activities and properties.
Used in Materials Science:
In materials science, sodium cyclopentadienide is a useful reagent for the preparation of cyclopentadienyl metal complexes, which are essential components in the synthesis of advanced materials with specific properties, such as conductivity, magnetism, and catalytic activity. These materials can be used in various applications, including electronics, energy storage, and sensors.
Used in Catalyst Preparation:
Sodium cyclopentadienide is also employed in the preparation of catalysts for various chemical reactions, such as polymerization, hydrogenation, and oxidation processes. The cyclopentadienyl metal complexes formed using sodium cyclopentadienide can act as highly efficient and selective catalysts, improving the yield and selectivity of the desired products in these reactions.

InChI:InChI=1/C5H5.Na/c1-2-4-5-3-1;/h1-3H,4H2;/rC5H5Na/c6-5-3-1-2-4-5/h1-3H,4H2

Synthetic route

bis(η3-allyl-μ-chloropalladium(II)) + sodium cyclopentadienylide (4984-82-1) → allyl(cyclopentadiene)palladium(II) (1271-03-0)

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

C12H17ClSi + sodium cyclopentadienylide (4984-82-1) → C17H22Si

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

C11H16ClNSi + sodium cyclopentadienylide (4984-82-1) → C16H21NSi

Conditions	Yield
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) + sodium cyclopentadienylide (4984-82-1) → C23H22

Conditions	Yield
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) + bis(trimethylsilyl)aminodichloroborane (6591-26-0) + sodium cyclopentadienylide (4984-82-1) → Li2[(cyclopentadiene)2BN(Si(CH3)3)2]

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%

1‐phenyl‐1‐chloro‐1‐silacyclohexane (29442-43-1) + sodium cyclopentadienylide (4984-82-1) → C16H20Si

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

C10H14ClNSi + sodium cyclopentadienylide (4984-82-1) → C15H19NSi

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

phenylmenthyl methanesulfonate + sodium cyclopentadienylide (4984-82-1) → ((-)-phenylmenthylcyclopentadienyl)lithium

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 + sodium cyclopentadienylide (4984-82-1) → C14H17NSi

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

zirconium tetrachloride bis(tetrahydrofuran) complex (21959-01-3, 125410-70-0, 125410-71-1) + bis(trimethylsilyl)aminodichloroborane (6591-26-0) + sodium cyclopentadienylide (4984-82-1) → [((CH3)3Si)2NB(η(5)-cyclopentadienyl)2]ZrCl2 (253798-57-1)

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%

1-chloro-1-phenyl-1-silacyclobutane (3401-28-3) + sodium cyclopentadienylide (4984-82-1) → C14H16Si

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

C10H14ClNSi + sodium cyclopentadienylide (4984-82-1) → C15H19NSi

Conditions	Yield
In tetrahydrofuran at 0℃; for 1.5h; Inert atmosphere;	96%

bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] + sodium cyclopentadienylide (4984-82-1) → allyl(cyclopentadiene)palladium(II) (1271-03-0)

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

C8H10ClNSi + sodium cyclopentadienylide (4984-82-1) → C13H15NSi

Conditions	Yield
In tetrahydrofuran at -50 - -45℃; for 3h; Inert atmosphere;	95%

1-chloro-1-phenylsilacyclopentane (7488-24-6) + sodium cyclopentadienylide (4984-82-1) → C15H18Si

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

C10H12Cl2O2Si + sodium cyclopentadienylide (4984-82-1) → C15H17ClO2Si

Conditions	Yield
In tetrahydrofuran at 0℃; for 6h; Inert atmosphere;	93%

N,N,N',N'-tetramethylsuccinamide (7334-51-2) + sodium cyclopentadienylide (4984-82-1) → 4-cyclopenta-2,4-dienylidene-4-dimethylamino-N,N-dimethyl-butyramide (765310-16-5)

Conditions	Yield
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) + sodium cyclopentadienylide (4984-82-1) → lithium trimethylsilylcyclopentadienylide

Conditions	Yield
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) + (dimethylamino)dibromoborane (7360-64-7) + sodium cyclopentadienylide (4984-82-1) → [(CH3)2NB(η(5)-cyclopentadienyl)2]ZrCl2 (253798-56-0)

Conditions	Yield
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%

tris(acetonitrile)tricarbonylmolybdenum(0) (15038-48-9, 17731-95-2) + phosphoric acid (86119-84-8, 7664-38-2) + sodium cyclopentadienylide (4984-82-1) → hydrido(tricarbonyl)(cyclopentadienyl)molybdenum (12176-06-6)

Conditions	Yield
Stage #1: tris(acetonitrile)tricarbonylmolybdenum(0); sodium cyclopentadienylide In tetrahydrofuran Inert atmosphere; Stage #2: phosphoric acid In tetrahydrofuran; water Reagent/catalyst;	90%

triethylsilyl chloride (994-30-9) + sodium cyclopentadienylide (4984-82-1) → lithium triethylsilylcyclopentadienylide

Conditions	Yield
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) → calcium dicyclopentadienide

Conditions	Yield
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) + sodium cyclopentadienylide (4984-82-1) → Cyclopenta-2,4-dienyl-(2,7-di-tert-butyl-9H-fluoren-9-yl)-dimethyl-silane (161853-50-5)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide In diethyl ether for 4h;	88%

2-Chloroethyl chloroformate (627-11-2) + sodium cyclopentadienylide (4984-82-1) → 2-Cyclopentadienylidene-1,3-dioxolane (67399-79-5)

Conditions	Yield
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) + sodium cyclopentadienylide (4984-82-1) → 2,6-bis(methylenecyclopentadienyl)pyridine disodium salt (136133-17-0)

Conditions	Yield
In tetrahydrofuran	85%

bis(trimethylsilyl)aminodichloroborane (6591-26-0) + hafnium tetrachloride (13499-05-3) + sodium cyclopentadienylide (4984-82-1) → [((CH3)3Si)2NB(η(5)-cyclopentadienyl)2]HfCl2 (253798-58-2)

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), HfCl4 and Et2O (-70°C), warming to room temp, stirring (2 h); filtration, pptn. (-30°C); elem. anal.;	85%

(2-chloroethyl)dimethylamine hydrochloride (4584-46-7) + sodium cyclopentadienylide (4984-82-1) → <2-(Dimethylamino)ethyl>cyclopentadien (147699-91-0)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran for 4h; Heating;	83%

Diethyl carbonate (105-58-8) + sodium cyclopentadienylide (4984-82-1) → sodium (ethoxycarbonyl)cyclopentadienide

Conditions	Yield
at 40 - 105℃; for 2.5h; Schlenk technique; Inert atmosphere;	83%

benzoic acid methyl ester (93-58-3) + sodium cyclopentadienylide (4984-82-1) → (benzoylcyclopentadienyl)sodium

Conditions	Yield
In tetrahydrofuran for 24h; Heating;	82%

choro(fluoren-9-yl)diphenylsilane (73220-53-8) + sodium cyclopentadienylide (4984-82-1) → cyclopentadienyl(fluoren-9-yl)diphenylsilane (162289-97-6)

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

Upstream product

• 77-73-6 bi(cyclopentadiene) 
• 542-92-7 cyclopenta-1,3-diene 
• 865-48-5 sodium t-butanolate 

Downstream Products

• 4045-44-7 1,2,3,4,5-pentamethylcyclopentadiene 
• 4249-10-9 1,2,3,4-tetramethylcyclopenta-1,3-diene 
• 4249-11-0 1,4,5,5-Tetramethyl-cyclopentadien 
• 4087-50-7 1,2,3,4,5,5-Hexamethyl-cyclopenta-1,3-diene 
• 26600-49-7 cyclopentylmethyl acetate 
• 193-85-1 azupyrene 
• 94548-84-2 4,8-Dimethyl-6-<β-phenyl-aethyl>-azulen 
• 119003-10-0 bis(cyclopentadienyl)phenylphosphine 
• 14060-53-8 6,6-Bis<4-(dimethylamino)phenyl>fulven 
• 114114-91-9 ((R)-2-Cyclopenta-2,4-dienyl-1-methoxy-ethyl)-benzene 
• 72895-55-7 <cyclopentadienyl>lithium 
• 114114-92-0 ((S)-2-Cyclopenta-2,4-dienyl-1-methoxy-ethyl)-benzene 
• 139678-03-8 4,8-dimethyl-6-(p-fluorophenyl)azulene 

Relevant articles and documents

Metallocene compounds, metallocene catalysts including the compounds and methods of polymerizing olefins with the catalysts

There are disclosed new metallocene compounds and catalysts for olefin polymerization. The metallocene compound is a complex of transition metal and cyclopentadienyl-type ligands substituted with silacycloalkyl group. The metallocene catalyst comprises the above metallocene compound and at least one activator such as aluminoxanes, aromatic boron compounds substituted with fluoride, and modified clays. The metallocene catalyst can be used for polymerization of olefin in liquid phase, slurry phase or gas phase process.

Process for producing hinokitiol

A process for producing hinokitiol which comprises the step of obtaining 1-isopropylcyclopentadiene from cyclopentadiene and an isopropylating agent represented by the general formula R—X wherein R is an isopropyl group and X is a halogen or the like (first step), reacting it with a dihaloketene to obtain a ketene adduct (second step), and decomposing the ketene adduct (third step), said first step comprising the following three steps: a) a preparation step of cyclopentadienyl metal; b) a step of obtaining isopropylcyclopentadiene by isopropylating the cyclopentadienyl metal in an aprotic polar solvent; and c) a step of isomerizing 5-isopropylcyclopentadiene in the product selectively to 1-isopropylcyclopentadiene with heat.

Process for the preparation of cyclopentadienyl metal salt and process for the preparation of derivative of cyclopentadiene using the same

A cyclopentadienyl metal salt is prepared by reacting a cyclopentadiene and a metal hydride in the presence of an amine compound. Furthermore, a derivative of a cyclopentadiene in which a phenyl group is bonded to its cyclopentadienyl moiety through an element of the 14 group of the Periodic Table is prepared using such a reaction.

Substituted cyclopentane compounds for use as chelating agents

The invention provides as new compounds cis-xis-cis-tetrasubstituted cyclopentane compounds which are expected to be useful as chelating agents for alkaline earths, transition, lanthanide, and actinide metal ions. The compounds have Formula (I). Each of the groups X1, X2, X3, and X4 comprises at least one potential ligand donor group, or one of the groups X or Z may comprise a group which may permit attachment to a biological active molecule or insoluble support. STR1

Asymmetric synthesis of optically active prostaglandins

An asymmetric synthesis of optically active prostaglandin F2α from cyclopentadiene including intermediates in this synthesis.