bis(cycloocta-1,5-diene) nickel

• ChemBase ID: 126167
• Molecular Formular: C16H24Ni
• Molecular Mass: 275.05516
• Monoisotopic Mass: 274.12314367
• SMILES: C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni]
• Canonical SMILES: C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni]
• InChI: InChI=1S/2C8H12.Ni/c2*1-2-4-6-8-7-5-3-1;/h2*1-2,7-8H,3-6H2;/b2*2-1-,8-7-
• InChIKey: JRTIUDXYIUKIIE-KZUMESAESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(cycloocta-1,5-diene) nickel; bis((1Z,5Z)-cycloocta-1,5-diene) nickel
• IUPAC Traditional name: bis(1,5-cyclooctadiene, (Z,Z)-) nickel; bis(1,5-cyclooctadiene) nickel
• Synonyms: Bis(cyclooctadiene)nickel; Ni(COD)2; Bis(1,5-cyclooctadiene)nickel(0); nickel biscod; Bis(cyclooctadiene)nickel(0); 双(1,5-环辛二烯)镍(0); 双(1,5-环辛二烯)镍(O)

Database IDs

• CAS Number: 1295-35-8
• EC Number: 215-072-0
• MDL Number: MFCD00058902
• PubChem SID: 162220508; 24854723
• PubChem CID: 6433264
• Chemspider ID: 17215769
• Wikipedia Title: Bis(cyclooctadiene)nickel(0)

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.832706
• LogD (pH = 7.4): 2.832706
• Log P: 2.832706
• Molar Refractivity: 39.0412 cm^3
• Polarizability: 14.319889 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Crystalline; Powder, Packaged under argon; Yellow solid
• Melting Point: 60 °C (dec.)(lit.); 60 °C with decomp.; 60°C dec.

Safety Information

• Storage Warning: Air Sensitive
• RTECS: QR6135000
• European Hazard Symbols: Flammable (F); Toxic (T); Harmful (Xn)
• UN Number: 1325; UN1325
• German water hazard class: 3
• Hazard Class: 4.1
• Packing Group: 2; II
• Risk Statements: 11-40; 45-11-43; R11-40
• Safety Statements: 36/37; 53-24-37-45-60; S36/37
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H228-H334-H351; H228-H350-H317
• GHS Precautionary statements: P210-P241-P302+P352-P321-P405-P501A; P210-P261-P281-P342 + P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1325 4.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: 96%
• Empirical Formula (Hill Notation): C16H24Ni

DETAILS

Sigma Aldrich - 244988

Application
Catalyst for the cycloaddition of 1,3-dienes.8
Used to catalyze the addition of allyl phenyl sulfide to alkynes leading to 1,4-dienes. The reaction with terminal acetylenes proceeds in high yield and high selectivity. A variety of functional groups are tolerated.
Reactant for:
• Oxidative addition reactions1Catalyst for:
• Asymmetric α-arylation and heteroarylation of ketones with chloroarenes2
• Cross-coupling reactions3
• Regioselective and stereoselective carboxylation/cyclization of allenyl aldehydes under a carbon dioxide atmosphere4
• Methyl carboxylation of homopropargylic alcohols5
• Stereoselective borylative ketone-diene coupling6
• Cycloaddition of benzamides with internal alkynes7
Packaging
2 g in glass bottle