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Merck
CN

214027

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24852821
EC Number:
223-743-4
Beilstein/REAXYS Number:
1849832
MDL number:
MFCD00001354

Key Documents

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Product Name

1,2,3,4,5-Pentamethylcyclopentadiene, 95%

InChI key

WQIQNKQYEUMPBM-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

95%

refractive index

n20/D 1.474 (lit.)

bp

58 °C/13 mmHg (lit.)

density

0.87 g/mL at 25 °C (lit.)

Quality Level

200

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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.

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.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

111.2 °F - closed cup

flash_point_c

44 °C - closed cup

ppe

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ4190
BCBV7825
BCBS9206V
BCBJ9905V
1451030V

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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)
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)
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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. It is also referred to as a cycloaddition.

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