244988

Bis(1,5-cyclooctadiene)nickel(0)

• Synonym(s): Bis(cyclooctadiene)nickel, Ni(COD)₂
• Empirical Formula (Hill Notation): C₁₆H₂₄Ni
• CAS Number: 1295-35-8
• Molecular Weight: 275.06
• EC Number: 215-072-0
• MDL number: MFCD00058902
• UNSPSC Code: 12352202
• PubChem Substance ID: 24854723
• NACRES: NA.22

Properties

• Quality Level: 200
• reaction suitability: core: nickel; reaction type: Cross Couplings; reagent type: catalyst
• parameter: temperature sensitive
• mp: 60 °C (dec.) (lit.)
• storage temp.: −20°C
• SMILES string: [Ni].C1CC=CCCC=C1.C2CC=CCCC=C2
• 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-;
• InChI key: JRTIUDXYIUKIIE-KZUMESAESA-N

Description

Application

Catalyst for the cycloaddition of 1,3-dienes.

Reactant for:

• Oxidative addition reactions

Catalyst for:

• Asymmetric α-arylation and heteroarylation of ketones with chloroarenes
• Cross-coupling reactions
• Regioselective and stereoselective carboxylation/cyclization of allenyl aldehydes under a carbon dioxide atmosphere
• Methyl carboxylation of homopropargylic alcohols
• Stereoselective borylative ketone-diene coupling
• Cycloaddition of benzamides with internal alkynes

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.

Safety Information

• Pictograms: GHS02,GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H228,H317,H351,H372
• Precautionary Statements: P202 - P210 - P240 - P280 - P302 + P352 - P308 + P313
• Hazard Classifications: Carc. 2 - Flam. Sol. 1 - Skin Sens. 1 - STOT RE 1
• Target Organs: Lungs
• Storage Class Code: 4.1B - Flammable solid hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves