BIS(1,5-CYCLOOCTADIENE)NICKEL(0)

BIS(1,5-CYCLOOCTADIENE)NICKEL(0) Basic information
Product Name:BIS(1,5-CYCLOOCTADIENE)NICKEL(0)
Synonyms:Bis(1,5-cyclooctadiene)nickel(O), 98+%;Bis(1,5-cyclooctadiene)nickel(0) 1GR;Bis(1,5-cyclooctadiene)nickel(0) 5GR;Bis(1,5-cyclooctadiene)nickel (0),98% Ni(COD)2;bis(1,5-cyclooctadiene)-nicke;Bis(1,5-cyclooctadiene)nickel;Bis(cyclooctadiene)nickel;Bis-1,5-cyclooctadienylnickel
CAS:1295-35-8
MF:C16H24Ni
MW:275.06
EINECS:215-072-0
Product Categories:organometallic complexes;Ni
Mol File:1295-35-8.mol
BIS(1,5-CYCLOOCTADIENE)NICKEL(0) Structure
BIS(1,5-CYCLOOCTADIENE)NICKEL(0) Chemical Properties
Melting point 60 °C (dec.)(lit.)
storage temp. -20°C
solubility Benzene (Partially Dissolved), THF (Slightly)
form Shiny Crystalline Powder
color Gold
Water Solubility Soluble in benzene, toluene, terahydrofuran, ether, dimethyl formamide, hexamethylphosphoramide, N-methylpyrrolidinone. Insoluble in water.
Sensitive Air Sensitive
Exposure limitsNIOSH: IDLH 10 mg/m3; TWA 0.015 mg/m3
Stability:Air Sensitive
CAS DataBase Reference1295-35-8(CAS DataBase Reference)
NIST Chemistry ReferenceNickel, bis[(1,2,5,6-«eta»)-1,5-cyclooctadiene]-(1295-35-8)
EPA Substance Registry SystemBis[(1,2,5,6-.eta.)-1,5-cyclooctadiene]nickel (1295-35-8)
Safety Information
Hazard Codes F,Xn,T
Risk Statements 11-40-45
Safety Statements 36/37-45-16-53
RIDADR UN 1325 4.1/PG 2
WGK Germany 3
RTECS QR6135000
TSCA No
HazardClass 4.2
PackingGroup I
HS Code 29319090
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
BIS(1,5-CYCLOOCTADIENE)NICKEL(0) Usage And Synthesis
Chemical PropertiesLight yellow to Brown powder to crystal.
UsesBis(1,5-cyclooctadiene)nickel(0) is used as a catalyst for the cycloaddition of 1,3-dienes and is used to catalyze the addition of allyl phenyl sulfide to alkynes leading to 1,4-dienes. Also, it is involved as a catalyst for asymmetric alpha-arylation and heteroarylation of ketones with chloroarenes, stereoselective borylative ketone-diene coupling, cycloaddition of benzamides with internal alkynes and methyl carboxylation of homopropargylic alcohols.
PreparationBis(1,5-cyclooctadiene)nickel(0) is prepared by reduction of anhydrous nickel(II) acetylacetonate in the presence of the diolefin:
Ni(acac)2 + 2 cod + 2 AlEt3 → Ni(cod)2 + 2 acacAlEt2 + C2H6 + C2H4
Ni(cod)2 is moderately soluble in several organic solvents. One or both 1,5-cyclooctadiene ligands are readily displaced by phosphines, phosphites, bipyridine, and isocyanides. If exposed to air, the solid oxidizes to nickel(II) oxide. As a result, this compound is generally handled in a glovebox.
ReactionsCatalyst for Grignard metathesis chain-growth polymerization of Poly(bithienylmethylene)s
Catalyst for neopentylglycolborylation of ortho-substituted aryl halides
Catalyst for Suzuki-Miyaura coupling reactions of heteroaryl ethers with arylboronic acids
Catalyst for carboxylation of naphthyl pivalates with CO2
Catalyst decarboxylative C?P cross-coupling of alkenyl acids with P(O)H compounds
Catalyst for direct amination of phenols via C–O Bond Activation using 2,4,6-Trichloro-1,3,5-triazine as reagent
Catalyst for conversion of aryl, heteroaryl and pharmaceutically relevant chlorides to the corresponding trifluoromethyl sulphides
Catalytic precursor for Suzuki–Miyaura cross-coupling reactions in water under very mild reaction conditions: (a) aryl–heteroaryl cross-couplings; (b) Hetero–heteroaryl cross-couplings
Bis(1,5-cyclooctadiene)nickel(0) Reaction 1
Bis(1,5-cyclooctadiene)nickel(0) Reaction 2
General DescriptionYellow crystals or yellowish green solid.
Reactivity ProfileBIS(1,5-CYCLOOCTADIENE)NICKEL(0) is extremely air and moisture sensitive. BIS(1,5-CYCLOOCTADIENE)NICKEL(0) is sensitive to exposure to light. BIS(1,5-CYCLOOCTADIENE)NICKEL(0) is incompatible with oxidizing agents, acids and acid fumes.
Fire HazardFlash point data for BIS(1,5-CYCLOOCTADIENE)NICKEL(0) are not available. BIS(1,5-CYCLOOCTADIENE)NICKEL(0) is probably combustible.
Purification MethodsIt is available in sealed ampoules under N2. All procedures should be carried out in a dry box and in an atmosphere of N2 or Argon in subdued light because the complex is light and oxygen sensitive, and flammable. The solid is washed with dry Et2O (under Ar) and separates from toluene as yellow crystals. Filter this under Ar gas pressure, place the crystals in a container and dry under a vacuum of 0.01mm to remove adhered toluene, flush with Ar and seal them under Ar or N2 in glass ampoules. [Semmelhack Org Reactions 19 115 and 178 1972, Wilke et al. Justus Liebigs Ann Chem 699 1 1966, Wender & Jenkins J Am Chem Soc 111 6432 1989, Fieser & Fieser Reagents for Org Synth 4 33, 16 29, 17 32.] SUSPECTED CARCINOGEN.
BIS(1,5-CYCLOOCTADIENE)NICKEL(0) Preparation Products And Raw materials
Cadmium bromide 1,5-CYCLOOCTADIENE 1,5-Cyclooctadiene BIS(1,5-CYCLOOCTADIENE)NICKEL(0)

Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.