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214027

1,2,3,4,5-Pentamethylcyclopentadiene

Name: 1,2,3,4,5-Pentamethylcyclopentadiene
Brand: ALDRICH

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

Assay:

95%

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Properties

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

Description

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.

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pictograms

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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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.

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)

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

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Global Trade Item Number

SKU	GTIN
214027-5G	04061838773098
214027-25G	04061838773081