Abstract
image
[
41749‐92‐2
]
or
[
14481‐08‐4
]
C
22
H
38
O
4
Ni
(MW 425.23)
InChI =
1S/2C11H20O2.Ni/c2*1‐10(2,3)8(12)7‐9(13)11(4,5)6;/h2*7,12H,1‐6H3;/q;;+2/p‐2/b2*8‐7‐
InChiKey =
PIIJAZNTPALBJL‐ATMONBRVSA‐L
(used as catalyst for polymerizations, oxidations, hydrofunctionalizations, amide alcoholysis, and cross‐coupling reactions)
Alternative Names
: nickel(II) bis(2,2,6,6‐tetramethyl‐3,5‐heptanedionate), Ni(TMHD)
2
, Ni(thd)
2
, Nickel(II) di(pivaloyl)methane, Ni(dpm)
2
.
Physical Data
: mp 219–225 °C.
1–3
bp (sublimation) 90–110 °C/0.1 mm Hg.
3
Solubility
: soluble in hexanes, toluene, dichloromethane, ethyl acetate, THF, and DMA; partially soluble in DMSO; insoluble in water.
Form Supplied in
: dark purple to light purple solid from commercial supplier (Strem catalog number 28‐0088). Recrystallized sample reported to be red needles; dry pink powder reported to turn blue on standing due to hydration.
1
Ni(TMHD)
2
·
x
H
2
O reported to be a green powder.
4
Analysis of Reagent Purity
: elemental analysis.
1
1
H NMR.
5
Preparative Methods
: mixing of methanolic solutions of 2,2,6,6‐tetramethylheptanedione and nickel(II) acetate tetrahydrate followed by the addition of water affords a precipitated solid which can be collected and dried.
1
Ultrasonic mixing of a solution of nickel(II) chloride hexahydrate and 2,2,6,6‐tetramethylheptanedione in methanol followed by pH adjustment affords a precipitated solid.
5
This material can also be purchased from commercial suppliers.
Purification
: recrystallization from hot dichloroethane.
1
Handling, Storage, and Precautions
: material can be handled under air with standard personal protective equipment. Dried samples will slowly hydrate on standing under ambient atmosphere.
1
Purified, dried samples should be stored under inert atmosphere in a glovebox or sealed in a desiccator and need only be used in a glovebox if hydration is to be avoided.