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Sigma-Aldrich

1,2,3,4,5-Pentamethylcyclopentadiene

95%

Sinonimo/i:

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

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5 G
153,00 €
25 G
437,00 €

153,00 €


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Cambia visualizzazione
5 G
153,00 €
25 G
437,00 €

About This Item

Formula empirica (notazione di Hill):
C10H16
Numero CAS:
Peso molecolare:
136.23
Beilstein:
1849832
Numero CE:
Numero MDL:
Codice UNSPSC:
12352100
ID PubChem:
NACRES:
NA.22

153,00 €


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Livello qualitativo

Saggio

95%

Indice di rifrazione

n20/D 1.474 (lit.)

P. ebollizione

58 °C/13 mmHg (lit.)

Densità

0.87 g/mL at 25 °C (lit.)

Stringa SMILE

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

InChI

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

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Descrizione generale

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]

Applicazioni

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]

Pittogrammi

Flame

Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

Flam. Liq. 3

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

111.2 °F - closed cup

Punto d’infiammabilità (°C)

44 °C - closed cup

Dispositivi di protezione individuale

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


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Certificati d'analisi (COA)

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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)
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)
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
Journal of Organometallic Chemistry, 472, 359-359 (1994)

Articoli

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.

Domande

1–2 di 2 domande  
  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 risposta
    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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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 risposta
    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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