214027

1,2,3,4,5-Pentamethylcyclopentadiene

95%

• Synonym(s): 1,2,3,4,5-Pentamethyl-1,3-cyclopentadiene
• Empirical Formula (Hill Notation): C₁₀H₁₆
• CAS Number: 4045-44-7
• Molecular Weight: 136.23
• Beilstein/REAXYS Number: 1849832
• EC Number: 223-743-4
• MDL number: MFCD00001354
• UNSPSC Code: 12352100
• PubChem Substance ID: 24852821
• NACRES: NA.22

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.

Safety Information

• pictograms: GHS02
• signalword: Warning
• hcodes: H226
• Hazard Classifications: Flam. Liq. 3
• Storage Class: 3 - Flammable liquids
• wgk_germany: 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