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Pentamethylcyclopentadiene information


Pentamethylcyclopentadiene
Skeletal formula of pentamethylcyclopentadiene
Ball-and-stick model of the pentamethylcyclopentadiene molecule
Names
Preferred IUPAC name
1,2,3,4,5-Pentamethylcyclopenta-1,3-diene
Identifiers
CAS Number
  • 4045-44-7 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 70069 ☒N
ECHA InfoCard 100.021.586 Edit this at Wikidata
PubChem CID
  • 77667
UNII
  • DSE3MRZ77C checkY
CompTox Dashboard (EPA)
  • DTXSID00193466 Edit this at Wikidata
InChI
  • InChI=1S/C10H16/c1-6-7(2)9(4)10(5)8(6)3/h6H,1-5H3 ☒N
    Key: WQIQNKQYEUMPBM-UHFFFAOYSA-N ☒N
  • InChI=1/C10H16/c1-6-7(2)9(4)10(5)8(6)3/h6H,1-5H3
    Key: WQIQNKQYEUMPBM-UHFFFAOYAI
SMILES
  • CC1=C(C)C(C)C(C)=C1C
Properties
Chemical formula
C10H16
Molar mass 136.238 g·mol−1
Appearance Colorless liquid[1]
Odor Mild[1]
Density 0.87 g/cm3[2]
Boiling point 55 to 60 °C (131 to 140 °F; 328 to 333 K) at 13 mmHg (1.7 kPa)
Solubility in water
Sparingly soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable
GHS labelling:
Pictograms
GHS02: Flammable
Signal word
Warning
Hazard statements
H226
Flash point 114 °C (237 °F; 387 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,2,3,4,5-Pentamethylcyclopentadiene is a cyclic diene with the formula C5(CH3)5H, often written C5Me5H, where Me is CH3.[3] It is a colorless liquid.[1]

1,2,3,4,5-Pentamethylcyclopentadiene is the precursor to the ligand 1,2,3,4,5-pentamethylcyclopentadienyl, which is often denoted Cp* (C5Me5) and read as "C P star", the "star" signifying the five methyl groups radiating from the core of the ligand. Thus, the 1,2,3,4,5-pentamethylcyclopentadiene's formula is also written Cp*H. In contrast to less-substituted cyclopentadiene derivatives, Cp*H is not prone to dimerization.

  1. ^ a b c https://pubchem.ncbi.nlm.nih.gov/compound/1_2_3_4_5-Pentamethylcyclopentadiene
  2. ^ https://www.sigmaaldrich.com/GB/en/sds/aldrich/214027
  3. ^ Elschenbroich, C.; Salzer, A. (1989). Organometallics: A Concise Introduction. VCH. p. 47. ISBN 9783527278183.

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Pentamethylcyclopentadiene

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1,2,3,4,5-Pentamethylcyclopentadiene is a cyclic diene with the formula C5(CH3)5H, often written C5Me5H, where Me is CH3. It is a colorless liquid. 1,2...

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C10H16

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refer to: Adamantane Camphene Carene Limonene Myrcene Ocimene Pentamethylcyclopentadiene Phellandrene Pinenes alpha-Pinene beta-Pinene Sabinene Syntin...

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Cyclopentadiene

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Cyclopentadienone Di-tert-butylcyclopentadiene Methylcyclopentadiene Pentamethylcyclopentadiene Pentacyanocyclopentadiene Most of these substituted cyclopentadienes...

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Decamethylzirconocene dichloride

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with the formula Cp*2ZrCl2 (where Cp* is C5(CH3)5, derived from pentamethylcyclopentadiene). It is a pale yellow, moisture sensitive solid that is soluble...

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Cyclopentadienyl complex

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have been commercialized for the production of polypropylene. Pentamethylcyclopentadiene gives rise to pentamethylcyclopentadienyl (Cp*) complexes. These...

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Decamethyltitanocene dichloride

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with the formula Cp*2TiCl2 (where Cp* is C5(CH3)5, derived from pentamethylcyclopentadiene). It is a red solid that is soluble in nonpolar organic solvents...

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Peter Maitlis

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unusual rearrangement reaction with hydrohalic acids to form a pentamethylcyclopentadiene derivative, and consequently can be used as a starting material...

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Dewar benzene

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potassium tetrachloroplatinate results in the formation of a pentamethylcyclopentadiene complex, [(η4-Cp*H)PtCl2], indicating that the rhodium and iridium...

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Methylcyclopentadiene

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spectra of some [(η5-C5H4Me)Fe(CO)(L)I] complexes". J. Organomet. Chem. 339 (3): 339–343. doi:10.1016/S0022-328X(00)99395-1. Pentamethylcyclopentadiene...

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Decamethylsilicocene

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as [HOEt 2][B(C 6F 5) 4]. Upon protonation, one equivalent of pentamethylcyclopentadiene is eliminated to produce the pentamethylcyclopentadienylsilicon(II)...

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Decamethylferrocene

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Decamethylferrocene is prepared in the same manner as ferrocene from pentamethylcyclopentadiene. This method can be used to produce other decamethylcyclopentadienyl...

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Bent metallocene

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complexes of fulvalene ligands. Bent metallocenes derived from pentamethylcyclopentadiene can undergo reactions involving the methyl groups. For example...

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Pentamethylcyclopentadienyl iridium dichloride dimer

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prepared by the reaction of hydrated iridium trichloride and pentamethylcyclopentadiene in hot methanol, from which the product precipitates 2 Cp*H +...

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Pentamethylcyclopentadienyl ruthenium dichloride dimer

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prepared by the reaction of hydrated ruthenium trichloride with pentamethylcyclopentadiene. 2 Cp*H + 2 RuCl3·3H2O → [Cp*RuCl2]2 + 2 HCl + 6 H2O The reaction...

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Jaqueline Kiplinger

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coordination polymers can be formed. (C5Me5)2Th(N3)2 utilizes pentamethylcyclopentadiene to form polymers with two bridging azide groups, while...

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Organotantalum chemistry

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Cp2TaH3. More soluble and better developed are derivatives of pentamethylcyclopentadiene such as Cp*TaCl4, Cp*2TaCl2, and Cp*2TaH3. Reduction of TaCl5...

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Pentamethylcyclopentadienyl rhodium dichloride dimer

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prepared by the reaction of rhodium trichloride trihydrate and pentamethylcyclopentadiene in hot methanol, from which the product precipitates: 2 C5(CH3)5H...

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Sterically induced reduction

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stable trivalent state. When Sm(III) is complexed with C 5Me 5 (pentamethylcyclopentadiene) to give the compound (C 5Me 5) 3Sm, this trivalent species has...

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Rhodocene

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tris(acetone) complex [(η5-C5Me5)Rh(Me2CO)3](BF4)2 by reaction with pentamethylcyclopentadiene, and the analogous iridium synthesis is also known. Decaisopropylrhodicnium...

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Europium compounds

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such as the reaction of europium and pentamethylcyclopentadiene to generate light orange bis(pentamethylcyclopentadiene) europium; and the reaction between...

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Germylene

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stabilization of this p-orbital is usually realized by coordination of a pentamethylcyclopentadiene (Cp*) ligand or of nitrogen (N), oxygen (O) or phosphorus (P)...

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Organoniobium chemistry

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complex followed by further functionalization. Derivatives of pentamethylcyclopentadiene are also known, such as (C5Me5)2NbH3. Niobium carbonyls supported...

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