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214027

Sigma-Aldrich

1,2,3,4,5-Pentamethylcyclopentadiene

95%

Synonym(s):

1,2,3,4,5-Pentamethyl-1,3-cyclopentadiene

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About This Item

Empirical Formula (Hill Notation):
C10H16
CAS Number:
4045-44-7
Molecular Weight:
136.23
Beilstein:
1849832
EC Number:
223-743-4
MDL number:
MFCD00001354
UNSPSC Code:
12352100
PubChem Substance ID:
24852821
NACRES:
NA.22

Quality Level

200

Assay

95%

refractive index

n20/D 1.474 (lit.)

bp

58 °C/13 mmHg (lit.)

density

0.87 g/mL at 25 °C (lit.)

SMILES string

CC1C(C)=C(C)C(C)=C1C

InChI

1S/C10H16/c1-6-7(2)9(4)10(5)8(6)3/h6H,1-5H3

InChI key

WQIQNKQYEUMPBM-UHFFFAOYSA-N

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General description

Mechanism of the Diels-Alder reaction of paramagneticendohedral metallofullerene and 1,2,3,4,5-pentamethylcyclopentadiene has been studied. Three-step large-scale preparation of 1,2,3,4,5-pentamethylcyclopentadiene has been reported. Reaction of 1,2,3,4,5-pentamethylcyclopentadiene (HCp*) with actinide ions in gas phase has been investigated by laser ablation mass spectrometry. It undergoes radical cation catalyzed cycloaddition with electron rich allenes to form Diels-Alder product.

Application

1,2,3,4,5-pentamethylcyclopentadiene was used as:
  • Growth modifier chemical, during metal organic chemical vapour deposition of iron from iron pentacarbonyl.
  • Ligand in "one-pot" iridium-catalyzed transformation of alcohols to amides via the intermediacy of oximes.
  • Raw material for the synthesis of [Cp*Rh(bpy)H2O]2+ (Cp* = pentamethylcyclopentadienyl, bpy = 2,2′-bipyridyl), an electron mediator in the regeneration process of NADH.

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

111.2 °F - closed cup

Flash Point(C)

44 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Satoru Sato et al.
Journal of the American Chemical Society, 135(15), 5582-5587 (2013-03-23)
The reaction mechanism of the Diels-Alder reaction of paramagneticendohedral metallofullerene, La@C82, and 1,2,3,4,5-pentamethylcyclopentadiene was studied theoretically and experimentally. Theoretical calculations revealed that this reaction proceeds via a concerted mechanism that includes formation of a stable intermediate. The activation energy of
Reactions of actinide ions with pentamethylcyclopentadiene: atypical hydrocarbon activation.
Gibson JK.
International Journal of Mass Spectrometry, 202(1), 19-29 (2000)
Nathan A Owston et al.
Organic letters, 9(1), 73-75 (2006-12-29)
[reaction: see text] The iridium catalyst [Ir(Cp*)Cl2]2 is effective for the rearrangement of oximes to furnish amides. The reaction has been combined with catalytic transfer hydrogenation between an alcohol and alkene to allow the conversion of alcohols into amides in
The Aminium Salt and Photoinduced Electron Transfer Initiated Diels-Alder Cycloaddition of Electron-rich Allenes: Evidence for a Stepwise Mechanism and the Importance of Steric and Electronic Effects for the Reactivity of Distonic Radical Cation Intermediates.
Schmittel M, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 2(8), 1031-1040 (1996)
Journal of Organometallic Chemistry, 472, 359-359 (1994)
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Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. Since the reaction involves the formation of a cyclic product via a cyclic transition state, it is also referred to as a "cycloaddition".

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