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Sigma-Aldrich

1,2,3,4,5-Pentamethylcyclopentadiene

95%

Synonyme(s) :

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

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5 G
287,00 $
25 G
1 140,00 $

About This Item

Formule empirique (notation de Hill) :
C10H16
Numéro CAS:
Poids moléculaire :
136.23
Beilstein:
1849832
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352100
ID de substance PubChem :
Nomenclature NACRES :
NA.22

287,00 $


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Niveau de qualité

Essai

95%

Indice de réfraction

n20/D 1.474 (lit.)

pb

58 °C/13 mmHg (lit.)

Densité

0.87 g/mL at 25 °C (lit.)

Chaîne SMILES 

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

InChI

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

Clé InChI

WQIQNKQYEUMPBM-UHFFFAOYSA-N

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Description générale

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

Application

1,2,3,4,5-pentamethylcyclopentadiene was used as:
  • Growth modifier chemical, during metal organic chemical vapour deposition of iron from iron pentacarbonyl.[5]
  • Ligand in "one-pot" iridium-catalyzed transformation of alcohols to amides via the intermediacy of oximes.[6]
  • 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.[7]

Pictogrammes

Flame

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

Flam. Liq. 3

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

111.2 °F - closed cup

Point d'éclair (°C)

44 °C - closed cup

Équipement de protection individuelle

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


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Consulter la Bibliothèque de documents

An improved synthesis of 1,2,3,4,5-pentamethylcyclopentadiene.
Kohl FX and Jutzi P.
Journal of Organometallic Chemistry, 243(1), 119-121 (1983)
Synth. React. Inorg. Met.-Org. Chem. , 24, 395-395 (1994)
Reactions of actinide ions with pentamethylcyclopentadiene: atypical hydrocarbon activation.
Gibson JK.
International Journal of Mass Spectrometry, 202(1), 19-29 (2000)
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
Journal of Organometallic Chemistry, 472, 359-359 (1994)

Articles

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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