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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:
Molecular Weight:
136.23
Beilstein:
1849832
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

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.[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]

Pictograms

Flame

Signal Word

Warning

Hazard Statements

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

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Certificates of Analysis (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 use of 1, 2, 3, 4, 5 pentamethylcyclopentadiene as an in situ growth modifier chemical for the chemical vapour deposition of iron from iron pentacarbonyl.
Lane PA and Wright PJ.
Journal of Crystal Growth, 204(3), 298-301 (1999)
Bio-inspired NADH regeneration by carbon nitride photocatalysis using diatom templates.
Liu J and Antonietti M.
Energy & Environmental Science, 6(5), 1486-1493 (2013)
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.

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.

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.

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. 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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    1 answer
    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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