1,2,3,4,5-pentamethylcyclopenta-1,3-diene

• ChemBase ID: 61447
• Molecular Formular: C10H16
• Molecular Mass: 136.23404
• Monoisotopic Mass: 136.12520051
• SMILES: C1(=C(C(=C(C1C)C)C)C)C
• Canonical SMILES: CC1C(=C(C(=C1C)C)C)C
• InChI: InChI=1S/C10H16/c1-6-7(2)9(4)10(5)8(6)3/h6H,1-5H3
• InChIKey: WQIQNKQYEUMPBM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,2,3,4,5-pentamethylcyclopenta-1,3-diene
• IUPAC Traditional name: pentamethylcyclopentadiene
• Synonyms: 1,2,3,4,5-Pentamethylcyclopentadiene; 1,2,3,4,5-Pentamethylcyclopentadiene; Pentamethylcyclopentadiene; 1,2,3,4,5-五甲基环戊二烯

Database IDs

• CAS Number: 4045-44-7
• EC Number: 223-743-4
• MDL Number: MFCD00001354
• Beilstein Number: 1849832
• PubChem SID: 24852821; 24887059; 162027188
• PubChem CID: 77667
• Wikipedia Title: Pentamethylcyclopentadiene

CALCULATED PROPERTIES

• Acid pKa: 16.574366
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.7594643
• LogD (pH = 7.4): 2.7594643
• Log P: 2.7594643
• Molar Refractivity: 46.9148 cm^3
• Polarizability: 18.013159 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Sparingly soluble in water
• Boiling Point: 55–60 °C (13 mm Hg); 57-58°C/13mm; 58 °C/13 mmHg(lit.)
• Flash Point: 111.2 °F; 114 °C; 44 °C; 44°C(111°F)
• Density: 0.87 g/mL at 25 °C(lit.); 0.870
• Refractive Index: 1.4740; n20/D 1.474(lit.); n20/D 1.475

Safety Information

• Storage Warning: IRRITANT; Light Sensitive
• UN Number: 3295; UN3295
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10
• Safety Statements: 43h-60
• TSCA Listed: false; 否
• GHS Pictograms: GHS02
• GHS Signal Word: Warning
• GHS Hazard statements: H226
• GHS Precautionary statements: P210-P241-P280-P303+P361+P353-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3295 3/PG 3

Product Information

• Purity: ≥94.0% (GC); 90+%; 94%; 95%
• Grade: technical
• Empirical Formula (Hill Notation): C10H16

DETAILS

Sigma Aldrich - 214027

Application
Cyclopentadienyl (Cp) replacement ligand used to alter the stability and reactivity of organometallic complexes.1,2
Ligand recently used in a "one-pot" iridium-catalyzed transformation of alcohols to amides via the intermediacy of oximes.
Packaging
1, 5, 25 g in glass bottle

Sigma Aldrich - 76826

Other Notes
Ligand for preparing transition metal complexes of greater solubility and crystallinity than with cyclopentadiene1,2