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3264-82-2

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3264-82-2 Usage

Physical Properties

Emerald-green crystals; orthorhombic structure; density 1.455 g/cm3 at 17°C; melts at 230°C; soluble in water, alcohol, chloroform, benzene and toluene; insoluble in ether.

Uses

Different sources of media describe the Uses of 3264-82-2 differently. You can refer to the following data:
1. Bis(2,4-pentanediono)nickel is used as a catalyst in hydrogenation and other organic reactions.
2. Nickel(II) acetylacetonate is usefully soluble in organic solvents and is therefore used in the Grignard synthesis of nickelocene from cyclopentadienyl magnesium halides. More ionic nickel(II) salts such as the thiocyanate can be reacted with potassium cyclopentadienide in liquid ammonia.
3. Nickel Acetylacetonate is used in preparation method of Bisphenol Dipropargyl Ether and Cyanate Ester blending resin.

Preparation

Different sources of media describe the Preparation of 3264-82-2 differently. You can refer to the following data:
1. Nickel acetylacetonate is prepared by the reaction of acetylacetone with nickel chloride hexahydrate or nickel hydroxide, followed by crystallization: 2CH3C(=O)CH2C(=O)CH3 + Ni(OH)2 → Ni(CH3C(=O)CHC(=O)CH3)2 + 2H2O
2. Nickel(II) acetylacetonate is isolated as the dihydrate Ni(acac)2·2H2O from aqueous solutions of nickel(II) salts in the presence of acetylacetone and a weak base such as sodium acetate; it is readily dehydrated to the green anhydrous compound at 50° in vacuo. From ammoniacal solutions of nickel(II) salts the diammoniate Ni(acac)2·2NH3 precipitates; this also readily evolves the two extra ligands to give the green acetylacetonate.

Chemical Properties

Nickel(II) acetylacetonate Ni(CH3COCHCOCH3)2, is obtained as emerald green crystals by dehydration of the dihydrate at 50°C in vacuum; it has an unusual trimeric structure in the solid state. The dihydrate Ni(CH3COCH3)2.2H2O is prepared by the addition of acetylacetone to solutions of nickel(II) salts in the presence of a weak base such as sodium acetate. Nickel(II) acetylacetonate is soluble in organic solvents and finds use in the synthesis of organometallic compounds such as nickelocene and bis(cyclooctadiene) nickel. It is also industrially important as a catalyst component in the oligomerization of alkenes and in the conversion of acetylene to cyclooctatetraene.

Flammability and Explosibility

Notclassified

Safety Profile

Confirmed human carcinogen. Poison by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Wash the green solid with H2O, dry it in a vacuum desiccator and recrystallise it from MeOH. [Charles & Pawlikowski J Phys Chem 62 440 1958.] The complex can be conveniently dehydrated by azeotropic distillation with toluene, and the crystals may be isolated by concentrating the toluene solution. [Wilkinson et al. J Am Chem Soc 76 1970 1954, Beilstein 1 IV 3677.]

Check Digit Verification of cas no

The CAS Registry Mumber 3264-82-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,6 and 4 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 3264-82:
(6*3)+(5*2)+(4*6)+(3*4)+(2*8)+(1*2)=82
82 % 10 = 2
So 3264-82-2 is a valid CAS Registry Number.
InChI:InChI=1/2C5H8O2.Ni/c2*1-4(6)3-5(2)7;/h2*3,6H,1-2H3;/q;;+2/p-2/b2*4-3-;

3264-82-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (N0096)  Bis(2,4-pentanedionato)nickel(II) Hydrate  >98.0%(T)

  • 3264-82-2

  • 25g

  • 450.00CNY

  • Detail
  • TCI America

  • (N0096)  Bis(2,4-pentanedionato)nickel(II) Hydrate  >98.0%(T)

  • 3264-82-2

  • 100g

  • 1,220.00CNY

  • Detail
  • TCI America

  • (N0096)  Bis(2,4-pentanedionato)nickel(II) Hydrate  >98.0%(T)

  • 3264-82-2

  • 500g

  • 3,850.00CNY

  • Detail
  • Alfa Aesar

  • (18811)  Nickel(II) 2,4-pentanedionate, 95%   

  • 3264-82-2

  • 5g

  • 193.0CNY

  • Detail
  • Alfa Aesar

  • (18811)  Nickel(II) 2,4-pentanedionate, 95%   

  • 3264-82-2

  • 25g

  • 336.0CNY

  • Detail
  • Alfa Aesar

  • (18811)  Nickel(II) 2,4-pentanedionate, 95%   

  • 3264-82-2

  • 100g

  • 519.0CNY

  • Detail
  • Alfa Aesar

  • (18811)  Nickel(II) 2,4-pentanedionate, 95%   

  • 3264-82-2

  • 500g

  • 1716.0CNY

  • Detail
  • Aldrich

  • (283657)  Nickel(II)acetylacetonate  95%

  • 3264-82-2

  • 283657-5G

  • 424.71CNY

  • Detail
  • Aldrich

  • (283657)  Nickel(II)acetylacetonate  95%

  • 3264-82-2

  • 283657-25G

  • 1,411.02CNY

  • Detail
  • Aldrich

  • (283657)  Nickel(II)acetylacetonate  95%

  • 3264-82-2

  • 283657-50G

  • 2,468.70CNY

  • Detail
  • Aldrich

  • (329509)  Nickel(II)acetylacetonate  technical grade, 90%

  • 3264-82-2

  • 329509-25G

  • 1,423.89CNY

  • Detail

3264-82-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Bis(2,4-pentanediono)nickel

1.2 Other means of identification

Product number -
Other names Nickel(II) Acetylacetonate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3264-82-2 SDS

3264-82-2Synthetic route

N,N-diisopropylcarbamato nickel(II)

N,N-diisopropylcarbamato nickel(II)

acetylacetone
123-54-6

acetylacetone

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
In n-heptane N2; addn. of the starting Ni-compound to a solution of acetylacetone; immediate reaction;; filtration;;63%
sodium (Z)-4-oxopent-2-en-2-olate
1118-67-8

sodium (Z)-4-oxopent-2-en-2-olate

nickel dichloride

nickel dichloride

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
In solid solid-state synthesis from NiCl2 (14.7 mmol) and NaCH3COCHCOCH3 (27.0 mmol) by mechanical activation (vibrating quartz vessel for 2 h at 5 Hz); transferring product into dry box under inert atmosphere;; vac. sublimation (0.1 torr) at 150-200°C bath temp.;;24%
2(C6H5SiO2)6(6-)*6Ni(2+)*Na(1+)*Cl(1-)=((C6H5SiO2)6)2Ni6*NaCl

2(C6H5SiO2)6(6-)*6Ni(2+)*Na(1+)*Cl(1-)=((C6H5SiO2)6)2Ni6*NaCl

acetylacetone
123-54-6

acetylacetone

A

polynickelphenylsiloxane

polynickelphenylsiloxane

B

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
In diethyl ether byproducts: (PhSi(OH)O)6; acetylacetone was added to Ni compd. in Et2O; stirred at room temp. for 50 min; filtered; washed (Et2O); filtrate concd.; C6H6 added; filtered; dried inair; mother liquor evapd.; dried (vac.); elem. anal.;A 8.8%
B n/a
nickel(II) isopropoxide

nickel(II) isopropoxide

acetylacetone enol
26567-75-9

acetylacetone enol

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
byproducts: i-PrOH; Ni:enole=1:2;
nickel methanolate
7245-23-0, 128424-88-4

nickel methanolate

acetylacetone enol
26567-75-9

acetylacetone enol

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
byproducts: MeOH; Ni:enole=1:2;
acetylacetone
123-54-6

acetylacetone

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
With sodium acetate In ethanol dissolving Ni-acetate in ethanol; addn. of stoich. amt. of acetylacetone in a soln. of sodium acetate; keeping the system in a boiling-water bath;; pptn., filtering, washing and drying;;
C10H16N2NiO2

C10H16N2NiO2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
With acetyl acetone In acetylacetone quantitative reaction already in the cold;>99
Ni(C7H12NO)2

Ni(C7H12NO)2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
With acetyl acetone In acetylacetone quantitative reaction already in the cold;>99
Ni(C11H12NO)2

Ni(C11H12NO)2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
With acetyl acetone In acetylacetone quantitative reaction already in the cold;<99
C18H16N2NiO2

C18H16N2NiO2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
With acetyl acetone In acetylacetone quantitative reaction already in the cold;>99
Ni(C16H14NO)2

Ni(C16H14NO)2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
With acetyl acetone In acetylacetone quantitative reaction already in the cold;>99
Ni(C10H10NO)2

Ni(C10H10NO)2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
With acetyl acetone In acetylacetone quantitative reaction already in the cold;>99
Ni(C16H14NO)2

Ni(C16H14NO)2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
With acetyl acetone In acetylacetone quantitative reaction already in the cold;>99
Ni(C16H14NO)2

Ni(C16H14NO)2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
With acetyl acetone In acetylacetone quantitative reaction already in the cold;>99
Ni(C16H14NO)2

Ni(C16H14NO)2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
With acetyl acetone In acetylacetone quantitative reaction already in the cold;>99
Ni(C15H12NO)2

Ni(C15H12NO)2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
With acetyl acetone In acetylacetone quantitative reaction already in the cold;>99
CONi(OCC8H13)O2C5H7

CONi(OCC8H13)O2C5H7

A

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

B

tetracarbonyl nickel
13463-39-3, 71564-36-8

tetracarbonyl nickel

Conditions
ConditionsYield
With carbon monoxide byproducts: C8H13COCOC8H13; react. with CO at 20 °C;;
{Ni(acetylacetonate)2(4-benzoylpyridine)2}

{Ni(acetylacetonate)2(4-benzoylpyridine)2}

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
In neat (no solvent) Kinetics; byproducts: 4-benzoylpyridine; thermal decompn. at 273°C;;
trans-[Ni(acetylacetonato)2(PMe2Ph)2]
1236196-28-3

trans-[Ni(acetylacetonato)2(PMe2Ph)2]

A

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

B

Dimethyl(phenyl)phosphine
672-66-2

Dimethyl(phenyl)phosphine

Conditions
ConditionsYield
In not given decomposition of nickel compd.; other compds. were detected;
bis(2,4-pentanedionate)nickel(II) dihydrate

bis(2,4-pentanedionate)nickel(II) dihydrate

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
In neat (no solvent) heating nickel compd. in vac. at 90°C for 12 h;
nickel(II) nitrate hexahydrate

nickel(II) nitrate hexahydrate

acetylacetone
123-54-6

acetylacetone

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

Conditions
ConditionsYield
With NaOH In neat (no solvent) Ni(NO3)2*6H2O, NaOH, acetylacetone (1:2:4 molar ratio) ground (15 min, room temp.); dried (vac., 100°C, 10 h);
nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

tetracarbonyl nickel
13463-39-3, 71564-36-8

tetracarbonyl nickel

Conditions
ConditionsYield
With diisobutylaluminium hydride In tetrahydrofuran; toluene to a soln. of Ni-complex in THF at room temp. under CO a soln. of ligand in toluene was added dropwise; ppt. was distd. continuously into the internal graduate vessel, excess of Ni(CO)4 was warmed both circulating fluids up to 60°C, N2 was let to pass through the vessel for 3-4 h;99%
With n-butyllithium In tetrahydrofuran; toluene to a soln. of Ni-complex in THF at room temp. under CO a soln. of ligand in toluene was added dropwise; ppt. was distd. continuously into the internal graduate vessel, excess of Ni(CO)4 was warmed both circulating fluids up to 60°C, N2 was let to pass through the vessel for 3-4 h;99%
With n-propylmagnesium bromide In tetrahydrofuran; toluene to a soln. of Ni-complex in THF at room temp. under CO a soln. of ligand in toluene was added dropwise; ppt. was distd. continuously into the internal graduate vessel, excess of Ni(CO)4 was warmed both circulating fluids up to 60°C, N2 was let to pass through the vessel for 3-4 h;97%
2-bromo-5,10,15,20-tetraphenylporphyrin

2-bromo-5,10,15,20-tetraphenylporphyrin

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

(2-bromo-5,10,15,20-tetraphenylporphyrinato)nickel(II)
52588-61-1

(2-bromo-5,10,15,20-tetraphenylporphyrinato)nickel(II)

Conditions
ConditionsYield
In 1,2-dichloro-ethane porphyrin dissolved with warming, Ni compd. added, reacted for 45 min; solvent removed (vac.), crystd. (CH2Cl2/pentane), washed (pentane);99%
oxomolybdenum(VI) methoxide
126769-40-2

oxomolybdenum(VI) methoxide

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

A

oxomolybdenum(VI) acetylacetonate methoxide

oxomolybdenum(VI) acetylacetonate methoxide

B

dinickel(II) dioxomolybdenum(VI) bis(acetylacetonate)(metoxide)10

dinickel(II) dioxomolybdenum(VI) bis(acetylacetonate)(metoxide)10

Conditions
ConditionsYield
In not given XRD;A n/a
B 99%
(3,5-F2C6H3)3((MeO)2C10H5)C20H10N4

(3,5-F2C6H3)3((MeO)2C10H5)C20H10N4

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

[5-(4,7-dimethoxynaphth-1-yl)-10,15,20-tris(3,5-difluorophenyl)porphyrinato]nickel(II)
1350372-44-9

[5-(4,7-dimethoxynaphth-1-yl)-10,15,20-tris(3,5-difluorophenyl)porphyrinato]nickel(II)

Conditions
ConditionsYield
In toluene reaction of nickel compd. with porphyrin deriv. in toluene at 100°C for 5 h;99%
diethylaluminium chloride
96-10-6

diethylaluminium chloride

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

A

Ni(acetylacetonate)2(triphenylphosphine)
31200-71-2

Ni(acetylacetonate)2(triphenylphosphine)

B

[((C6H5)3P)3NiCl]2

[((C6H5)3P)3NiCl]2

Conditions
ConditionsYield
With triphenylphosphine In diethyl ether byproducts: C2H6, C2H4, H2; Ar-atmosphere; addn. of Et2AlCl to suspn. of 6 equiv. Ni-complex and 6 equiv. PPh3 (-40°C), stirring (4 h, room temp., pptn.); filtration, washing (ether), drying (vac.); elem. anal.; gas chromy. ofbyproducts;A 30.9%
B 98%
nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

N,N'-bis-(2-methyl-2-mercaptoprop-1-yl)-1,3-diamino-2,2-dimethylpropane
134777-42-7

N,N'-bis-(2-methyl-2-mercaptoprop-1-yl)-1,3-diamino-2,2-dimethylpropane

N,N'-bis-(2-methyl-2-mercaptoprop-1-yl)-1,3-diamino-2,2-dimethylpropanenickel(II)
870694-90-9, 308323-03-7

N,N'-bis-(2-methyl-2-mercaptoprop-1-yl)-1,3-diamino-2,2-dimethylpropanenickel(II)

Conditions
ConditionsYield
In dichloromethane soln. of Ni-complex in CH2Cl2 was added to soln. of ligand in CH2Cl2; concd., ether was added, filtered, washed with ether, dried in air;98%
(H2(C6F5)3(C5H2N)2C5HNO)2

(H2(C6F5)3(C5H2N)2C5HNO)2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

(C6F5)6C30H10N6O2Ni2
500116-51-8

(C6F5)6C30H10N6O2Ni2

Conditions
ConditionsYield
In toluene refluxing toluene-soln.;95%
C12H6(NC6H2(CH3)C6H4C2H4C6H4)2

C12H6(NC6H2(CH3)C6H4C2H4C6H4)2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

trityl tetrakis(pentafluorophenyl)borate

trityl tetrakis(pentafluorophenyl)borate

[((CH3)2C52H34N2)Ni(acetylacetonate)](tetrakis(pentafluorophenyl)borate)
1175097-04-7

[((CH3)2C52H34N2)Ni(acetylacetonate)](tetrakis(pentafluorophenyl)borate)

Conditions
ConditionsYield
In diethyl ether; dichloromethane (N2); addn. of dry CH2Cl2 and dry ether to mixt. of nickel compd., diimine deriv. and trityl salt, stirring at room temp. for 1 h; addn. of pentane, decantation, washing with diethyl ether and pentane, drying in vac. for 2 ds, elem. anal.;93%
(2,4,6-Me3C6H2)3((MeO)2C10H5)C20H10N4

(2,4,6-Me3C6H2)3((MeO)2C10H5)C20H10N4

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

[5-(4,7-dimethoxynaphth-1-yl)-10,15,20-trimesitylporphyrinato]nickel(II)
1350372-43-8

[5-(4,7-dimethoxynaphth-1-yl)-10,15,20-trimesitylporphyrinato]nickel(II)

Conditions
ConditionsYield
In toluene reaction of nickel compd. with porphyrin deriv. in toluene at 100°C for 5 h;93%
ethene
74-85-1

ethene

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

tricyclohexylphosphine
2622-14-2

tricyclohexylphosphine

ethene-bis(tricyclohexylphosphane)-nickel(0)
41685-59-0

ethene-bis(tricyclohexylphosphane)-nickel(0)

Conditions
ConditionsYield
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;91%
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;91%
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;63%
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;63%
triethylaluminum
97-93-8

triethylaluminum

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

o-diphenylphosphinostyrene
17165-18-3

o-diphenylphosphinostyrene

bis{(2-vinylphenyl)diphenylphosphine}nickel(0)
113509-30-1

bis{(2-vinylphenyl)diphenylphosphine}nickel(0)

Conditions
ConditionsYield
With butadiene In toluene Under inert atmosphere, cooling a soln. of anhyd. Ni(acac)2 and the organic ligand to -50°C, condensing dry butadiene into the soln., slow addn. of AlEt3 while holding the temp. at -20°C, stirring overnight (warming to room temp.).; Cooling of resulting yellow soln. to -70°C, addn. of hexane gives a bright yellow ppt. immediately, filtn., washing (hexane, cold ether), drying in vac.;91%
5,10,15-tris(pentafluorophenyl)-20-(o-nitrophenyl)porphyrin

5,10,15-tris(pentafluorophenyl)-20-(o-nitrophenyl)porphyrin

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

5-(nitrophenyl)-10,15,20-tri(pentafluorophenyl)porphyrinato nickel(II)
507489-09-0

5-(nitrophenyl)-10,15,20-tri(pentafluorophenyl)porphyrinato nickel(II)

Conditions
ConditionsYield
In xylene reaction under reflux;91%
(2-mercaptoethyl)diphenylphosphine
3190-79-2

(2-mercaptoethyl)diphenylphosphine

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

trans-bis((2-thiolatoethyl)diphenylphosphine)nickel(II)
90668-33-0

trans-bis((2-thiolatoethyl)diphenylphosphine)nickel(II)

Conditions
ConditionsYield
In toluene (Ar); addn. of (C6H5)2PCH2CH2SH (20 mmol) to a soln. of Ni(CH3COCHCOCH3)2 (10 mmol) in toluene;; pptn.; washing with toluene and diethyl ether; drying in vac.; recrystn. from CH2Cl2/hexane or CH2Cl2/Et2O; elem. anal.;;90%
C20H4N4(CH3)6(C2H5)2C6H3(OCH3)2(C6H4)(C9H3N2)(CH3)2(C2H5)2(C2H5CO2)2

C20H4N4(CH3)6(C2H5)2C6H3(OCH3)2(C6H4)(C9H3N2)(CH3)2(C2H5)2(C2H5CO2)2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

NiC20H2N4(CH3)6(C2H5)2C6H3(OCH3)2(C6H4)(C9H3N2)(CH3)2(C2H5)2(CO2C2H5)2
176651-36-8

NiC20H2N4(CH3)6(C2H5)2C6H3(OCH3)2(C6H4)(C9H3N2)(CH3)2(C2H5)2(CO2C2H5)2

Conditions
ConditionsYield
In o-xylene (N2); in the dark; reflux(4 h), evapn. of the solvent; chromatography (alumina), crystn. (CH2Cl2, cyclohexane); elem. anal.;90%
C20H8N4(C6H5)3(C6H4CH)O

C20H8N4(C6H5)3(C6H4CH)O

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

[Ni(C20H6N4(C6H5)3(C6H4CH)O)]*0.5H2O

[Ni(C20H6N4(C6H5)3(C6H4CH)O)]*0.5H2O

Conditions
ConditionsYield
In toluene mixt. of ketoporphyrin and Ni acetylacetonate in toluene heated under reflux overnight; chromy. (silica gel, CH2Cl2), crystn. from CH2Cl2/MeOH; elem. anal.;90%
C20H10N4-5,10-(3,5-(Me2CHCH2CH2O)2C6H3)2-15,20-[CCC20H10BrN4-10',20'-(C6H3-3,5-(OCH2CH2CHMe2)2)2]2

C20H10N4-5,10-(3,5-(Me2CHCH2CH2O)2C6H3)2-15,20-[CCC20H10BrN4-10',20'-(C6H3-3,5-(OCH2CH2CHMe2)2)2]2

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

NiC20H8N4-5,10-(3,5-(Me2CHCH2CH2O)2C6H3)2-15,20-[CCC20H8N4BrNi-10';20'-(C6H3-3,5-(OCH2CH2CHMe2)2)2]2
721922-85-6

NiC20H8N4-5,10-(3,5-(Me2CHCH2CH2O)2C6H3)2-15,20-[CCC20H8N4BrNi-10';20'-(C6H3-3,5-(OCH2CH2CHMe2)2)2]2

Conditions
ConditionsYield
In toluene87%
ethene
74-85-1

ethene

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

triphenylphosphine
603-35-0

triphenylphosphine

bis(triphenylphosphine)ethylenenickel(0)
23777-40-4

bis(triphenylphosphine)ethylenenickel(0)

Conditions
ConditionsYield
With triethylaluminum In diethyl ether prepn. in ether at 0 °C;;85%
With Al(C2H5)3 In diethyl ether prepn. in ether at 0 °C;;85%
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;<=95
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;<=95
ethene
74-85-1

ethene

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

triethylphosphine
554-70-1

triethylphosphine

bis(triethylphosphane)mono(ethene)nickel(0)
41051-87-0

bis(triethylphosphane)mono(ethene)nickel(0)

Conditions
ConditionsYield
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;85%
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;85%
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;70%
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;70%
ethene
74-85-1

ethene

C30H51O3P
93634-84-5

C30H51O3P

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

π-C2H4Ni(P(OC10H17)3)2
54721-04-9

π-C2H4Ni(P(OC10H17)3)2

Conditions
ConditionsYield
With Al(C2H5)3 In diethyl ether prepn. in ether at -50 °C up to room temp.;;85%
C20H8N4(C6H4CH3)3(C6H3(CH3)CH)O

C20H8N4(C6H4CH3)3(C6H3(CH3)CH)O

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

[Ni(C20H6N4(C6H4CH3)3(C6H3(CH3)CH)O)]*H2O

[Ni(C20H6N4(C6H4CH3)3(C6H3(CH3)CH)O)]*H2O

Conditions
ConditionsYield
In toluene mixt. of ketoporphyrin and Ni acetylacetonate in toluene heated under reflux overnight; chromy. (silica gel, CH2Cl2), crystn. from CH2Cl2/MeOH; elem. anal.;85%
{(CH3)3NH}{1.2-C2B9H12}

{(CH3)3NH}{1.2-C2B9H12}

tetramethlyammonium chloride
75-57-0

tetramethlyammonium chloride

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

{(CH3)4N}{Ni(1.2-dicarba-undecahydro-closo-undecaborate)2}
51159-92-3

{(CH3)4N}{Ni(1.2-dicarba-undecahydro-closo-undecaborate)2}

Conditions
ConditionsYield
With NaH; O2 In tetrahydrofuran prepn. of Na2(C2B9H11) soln. by react. of ((CH3)3NH)(C2B9H12) and NaH in boiling THF and evapn. of N(CH3)3 in N2 stream, treating nickel acetylacetonate with this soln. at 35 °C (3 h), oxidn. by introduction of O2, processing with (N(CH3)4)Cl;;84%
With NaH; O2 In tetrahydrofuran prepn. of Na2(C2B9H11) soln. by react. of ((CH3)3NH)(C2B9H12) and NaH in boiling THF and evapn. of N(CH3)3 in N2 stream, treating nickel acetylacetonate with this soln. at 35 °C (3 h), oxidn. by introduction of O2, processing with (N(CH3)4)Cl;;84%
1-hexene
592-41-6

1-hexene

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

tricyclohexylphosphine
2622-14-2

tricyclohexylphosphine

C4H9CHCH2Ni(P(C6H11-cyclo)3)2
76160-45-7

C4H9CHCH2Ni(P(C6H11-cyclo)3)2

Conditions
ConditionsYield
With Al(CH3)3 or (C2H5)2AlOC2H5 or Al(C4H9-i)3 In not given redn. of Ni acetylacetonate with Al org. compound in benzene or toluene soln.;;84%
With Al(CH3)3 or (C2H5)2AlOC2H5 or Al(C4H9-i)3 In not given redn. of Ni acetylacetonate with Al org. compound in benzene or toluene soln.;;84%
trans-rac-N,N'-bis(2-mercapto-2-methylprop-1-yl)-1,2-cyclohexanediamine

trans-rac-N,N'-bis(2-mercapto-2-methylprop-1-yl)-1,2-cyclohexanediamine

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

trans-rac-N,N'-bis(2-mercapto-2-methylprop-1-yl)-1,2-cyclohexanediaminenickel(II)

trans-rac-N,N'-bis(2-mercapto-2-methylprop-1-yl)-1,2-cyclohexanediaminenickel(II)

Conditions
ConditionsYield
In acetonitrile soln. of ligand in MeCN was added to suspn. of Ni-complex in MeCN, stirred overnight; filtered, washed with MeCN, dried in vacuo;84%
[H2(C4H2NCC6H5)3(C4H2NCC6H4C6H4NNC5H4N)]

[H2(C4H2NCC6H5)3(C4H2NCC6H4C6H4NNC5H4N)]

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

[Ni(C4H2NCC6H5)3(C4H2NCC6H4C6H4NNC5H4N)]

[Ni(C4H2NCC6H5)3(C4H2NCC6H4C6H4NNC5H4N)]

Conditions
ConditionsYield
In toluene stoich. mixt., for 3 h;84%
ethene
74-85-1

ethene

tris(2-methoxyphenyl) phosphite
36370-75-9

tris(2-methoxyphenyl) phosphite

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

C2H4Ni(P(OC6H4OCH3)3)2
63517-34-0

C2H4Ni(P(OC6H4OCH3)3)2

Conditions
ConditionsYield
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;83%
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;83%
triisopropyl phosphite
116-17-6

triisopropyl phosphite

triethylaluminum
97-93-8

triethylaluminum

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

<(i-PrO)3P>3Ni-Et

<(i-PrO)3P>3Ni-Et

Conditions
ConditionsYield
In toluene treatment of 3.89 mM Ni(acac)2 in dry toluene with 15.56 mM P(i-OPr)3 and cooling to -10 - - 15°C; stirring under Ar and addn. of 11.67 mM AlEt3; stirring mixture 10 min at -15°C; addn. of i-PrOH and MeCN;; pptn.; washing with cold dry MeCN and drying in vacuo at 20°C;;83%
ethene
74-85-1

ethene

tris(2-phenylphenyl)phosphite
2752-19-4

tris(2-phenylphenyl)phosphite

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

C2H4Ni(P(OC6H4C6H5)3)2
108537-21-9

C2H4Ni(P(OC6H4C6H5)3)2

Conditions
ConditionsYield
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;82%
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;82%
bis(1,2-di(perfluoroethyl)phosphino)ethane
120263-08-3

bis(1,2-di(perfluoroethyl)phosphino)ethane

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

[Ni(bis(1,2-diperfluoroethylphosphino)ethane)2]
616225-28-6

[Ni(bis(1,2-diperfluoroethylphosphino)ethane)2]

Conditions
ConditionsYield
With butadiene; Al(CH2CH(CH3)2)3 In hexane; toluene under N2, Schlenk technique; excess diphosphane added to suspn. of Ni acetylacetonate in hexane/toluene (1/1), mixt. cooled to -78°C, butadiene and Al(i-Bu)3 added, slowly warmed to room temp., stirred for 24 h; volatiles removed, residue triturated with petroleum ether, ppt. filtered off, washed with petroleum ether, dried under vac.; elem. anal.;82%
5-(4-carbomethoxynaphth-1-yl)-10,15,20-tris(2,4,6-trimethylphenyl)porphyrin

5-(4-carbomethoxynaphth-1-yl)-10,15,20-tris(2,4,6-trimethylphenyl)porphyrin

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

(5-(4-carbomethoxynaphth-1-yl)-10,15,20-tris(2,4,6-trimethylphenyl)porphyrin-2H)Ni
950856-49-2

(5-(4-carbomethoxynaphth-1-yl)-10,15,20-tris(2,4,6-trimethylphenyl)porphyrin-2H)Ni

Conditions
ConditionsYield
In toluene refluxed (110°C, 20 h); 1HNMR, MALDI-TOF MS;82%
nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

N,N'-dineopentyl-2-amino-5-alcoholate-1,4-benzoquinonemonoiminium
429693-77-6

N,N'-dineopentyl-2-amino-5-alcoholate-1,4-benzoquinonemonoiminium

Ni(C6H2(O)2(NHCH2C(CH3)3)(NCH2C(CH3)3))2
622784-51-4

Ni(C6H2(O)2(NHCH2C(CH3)3)(NCH2C(CH3)3))2

Conditions
ConditionsYield
In toluene under dry Ar atm. using Schlenk techniques; zwitterion dissolved in anhyd. toluene; acetylacetonate added; mixt. refluxed for 12 h; colled to room temp.; ppt. filtered; washed (cold toluene); elem. anal.;81%

3264-82-2Relevant articles and documents

Ferbinteanu, Marilena,Andruh, Marius,Segal, E.

, p. 241 - 248 (1991)

Nickel nanoparticles supported on MOF-5: Synthesis and catalytic hydrogenation properties

Zhao, Huahua,Song, Huanling,Chou, Lingjun

, p. 261 - 265 (2012/03/13)

Nickel nanoparticles (2-6 nm) were successfully deposited on MOF-5 (Zn 4O(BDC)3, BDC = 1,4-benzenedicarboxylate) by a facile wet impregnation strategy to prepare Ni@MOF-5 employing Ni(acac)2 (acac = acetylacetonate) as the precursor in absolute ethanol solvent owing to the sensitivity to the moisture of MOF-5. Ni@MOF-5 exhibited excellent catalytic activity for hydrogenation of C = C bond using crotonaldehyde as a probe molecule under mild reaction conditions (conversion > 90.0%, selectivity > 98.0%, 2.0 MPa, 100 °C, 40 min). In addition, the catalyst could be reused and the structure of MOF-5 framework was still maintained. Therefore, MOF-5 promised a novel candidate of support for hydrogenation catalyst.

Ni(acac)2/phosphine as an excellent precursor of nickel(0) for catalytic systems

Ananikov, Valentine P.,Gayduk, Konstantin A.,Starikova, Zoya A.,Beletskaya, Irina P.

, p. 5098 - 5102 (2011/01/05)

The coordination of phosphine ligands to nickel acetylacetonate was studied in toluene solution, and the first X-ray structure of the unstable complex trans-[Ni(acac)2(PMe2Ph)2] has been reported. A convenient procedure was developed to generate Ni(0) species in situ in solution from a Ni(acac)2 precursor, and their application in catalysis was demonstrated. A study of the reaction mechanism has suggested that water may play an important role in the formation of zerovalent nickel species. The nature of the Ni(0) species was confirmed by trapping with Ph 2S2, and the structure of the resulting complexes trans-[Ni(SPh)2L2] was established by X-ray analysis for L = PMe2Ph, PMePh2, PBu3.

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