Conditions | Yield |
---|---|
In n-heptane N2; addn. of the starting Ni-compound to a solution of acetylacetone; immediate reaction;; filtration;; | 63% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
byproducts: i-PrOH; Ni:enole=1:2; |
nickel methanolate
acetylacetone enol
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
byproducts: MeOH; Ni:enole=1:2; |
nickel diacetate
acetylacetone
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
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;; |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
With acetyl acetone In acetylacetone quantitative reaction already in the cold; | >99 |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
With acetyl acetone In acetylacetone quantitative reaction already in the cold; | >99 |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
With acetyl acetone In acetylacetone quantitative reaction already in the cold; | <99 |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
With acetyl acetone In acetylacetone quantitative reaction already in the cold; | >99 |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
With acetyl acetone In acetylacetone quantitative reaction already in the cold; | >99 |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
With acetyl acetone In acetylacetone quantitative reaction already in the cold; | >99 |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
With acetyl acetone In acetylacetone quantitative reaction already in the cold; | >99 |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
With acetyl acetone In acetylacetone quantitative reaction already in the cold; | >99 |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
With acetyl acetone In acetylacetone quantitative reaction already in the cold; | >99 |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
With acetyl acetone In acetylacetone quantitative reaction already in the cold; | >99 |
A
nickel(II) acetylacetonate
B
tetracarbonyl nickel
Conditions | Yield |
---|---|
With carbon monoxide byproducts: C8H13COCOC8H13; react. with CO at 20 °C;; |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
In neat (no solvent) Kinetics; byproducts: 4-benzoylpyridine; thermal decompn. at 273°C;; |
trans-[Ni(acetylacetonato)2(PMe2Ph)2]
A
nickel(II) acetylacetonate
B
Dimethyl(phenyl)phosphine
Conditions | Yield |
---|---|
In not given decomposition of nickel compd.; other compds. were detected; |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
In neat (no solvent) heating nickel compd. in vac. at 90°C for 12 h; |
Conditions | Yield |
---|---|
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
tetracarbonyl nickel
Conditions | Yield |
---|---|
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% |
nickel(II) acetylacetonate
(2-bromo-5,10,15,20-tetraphenylporphyrinato)nickel(II)
Conditions | Yield |
---|---|
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
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
In not given XRD; | A n/a B 99% |
nickel(II) acetylacetonate
[5-(4,7-dimethoxynaphth-1-yl)-10,15,20-tris(3,5-difluorophenyl)porphyrinato]nickel(II)
Conditions | Yield |
---|---|
In toluene reaction of nickel compd. with porphyrin deriv. in toluene at 100°C for 5 h; | 99% |
diethylaluminium chloride
nickel(II) acetylacetonate
A
Ni(acetylacetonate)2(triphenylphosphine)
Conditions | Yield |
---|---|
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
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)
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In toluene refluxing toluene-soln.; | 95% |
nickel(II) acetylacetonate
[((CH3)2C52H34N2)Ni(acetylacetonate)](tetrakis(pentafluorophenyl)borate)
Conditions | Yield |
---|---|
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% |
nickel(II) acetylacetonate
[5-(4,7-dimethoxynaphth-1-yl)-10,15,20-trimesitylporphyrinato]nickel(II)
Conditions | Yield |
---|---|
In toluene reaction of nickel compd. with porphyrin deriv. in toluene at 100°C for 5 h; | 93% |
ethene
nickel(II) acetylacetonate
tricyclohexylphosphine
ethene-bis(tricyclohexylphosphane)-nickel(0)
Conditions | Yield |
---|---|
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
nickel(II) acetylacetonate
o-diphenylphosphinostyrene
bis{(2-vinylphenyl)diphenylphosphine}nickel(0)
Conditions | Yield |
---|---|
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% |
nickel(II) acetylacetonate
5-(nitrophenyl)-10,15,20-tri(pentafluorophenyl)porphyrinato nickel(II)
Conditions | Yield |
---|---|
In xylene reaction under reflux; | 91% |
(2-mercaptoethyl)diphenylphosphine
nickel(II) acetylacetonate
trans-bis((2-thiolatoethyl)diphenylphosphine)nickel(II)
Conditions | Yield |
---|---|
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% |
nickel(II) acetylacetonate
NiC20H2N4(CH3)6(C2H5)2C6H3(OCH3)2(C6H4)(C9H3N2)(CH3)2(C2H5)2(CO2C2H5)2
Conditions | Yield |
---|---|
In o-xylene (N2); in the dark; reflux(4 h), evapn. of the solvent; chromatography (alumina), crystn. (CH2Cl2, cyclohexane); elem. anal.; | 90% |
Conditions | Yield |
---|---|
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% |
nickel(II) acetylacetonate
NiC20H8N4-5,10-(3,5-(Me2CHCH2CH2O)2C6H3)2-15,20-[CCC20H8N4BrNi-10';20'-(C6H3-3,5-(OCH2CH2CHMe2)2)2]2
Conditions | Yield |
---|---|
In toluene | 87% |
ethene
nickel(II) acetylacetonate
triphenylphosphine
bis(triphenylphosphine)ethylenenickel(0)
Conditions | Yield |
---|---|
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
nickel(II) acetylacetonate
triethylphosphine
bis(triethylphosphane)mono(ethene)nickel(0)
Conditions | Yield |
---|---|
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
C30H51O3P
nickel(II) acetylacetonate
π-C2H4Ni(P(OC10H17)3)2
Conditions | Yield |
---|---|
With Al(C2H5)3 In diethyl ether prepn. in ether at -50 °C up to room temp.;; | 85% |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
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% |
tetramethlyammonium chloride
nickel(II) acetylacetonate
{(CH3)4N}{Ni(1.2-dicarba-undecahydro-closo-undecaborate)2}
Conditions | Yield |
---|---|
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
nickel(II) acetylacetonate
tricyclohexylphosphine
C4H9CHCH2Ni(P(C6H11-cyclo)3)2
Conditions | Yield |
---|---|
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% |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
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% |
nickel(II) acetylacetonate
Conditions | Yield |
---|---|
In toluene stoich. mixt., for 3 h; | 84% |
ethene
tris(2-methoxyphenyl) phosphite
nickel(II) acetylacetonate
C2H4Ni(P(OC6H4OCH3)3)2
Conditions | Yield |
---|---|
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;; | 83% |
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;; | 83% |
Conditions | Yield |
---|---|
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
tris(2-phenylphenyl)phosphite
nickel(II) acetylacetonate
C2H4Ni(P(OC6H4C6H5)3)2
Conditions | Yield |
---|---|
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
nickel(II) acetylacetonate
[Ni(bis(1,2-diperfluoroethylphosphino)ethane)2]
Conditions | Yield |
---|---|
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% |
nickel(II) acetylacetonate
(5-(4-carbomethoxynaphth-1-yl)-10,15,20-tris(2,4,6-trimethylphenyl)porphyrin-2H)Ni
Conditions | Yield |
---|---|
In toluene refluxed (110°C, 20 h); 1HNMR, MALDI-TOF MS; | 82% |
nickel(II) acetylacetonate
N,N'-dineopentyl-2-amino-5-alcoholate-1,4-benzoquinonemonoiminium
Ni(C6H2(O)2(NHCH2C(CH3)3)(NCH2C(CH3)3))2
Conditions | Yield |
---|---|
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% |
The Nickel acetylacetonate, with the CAS registry number 3264-82-2, is also known as Bis(2,4-pentanediono)nickel. It belongs to the product categories of Catalysts for Organic Synthesis; Classes of Metal Compounds; Homogeneous Catalysts; Metal Complexes; Ni (Nickel) Compounds; Synthetic Organic Chemistry; Transition Metal Compounds; Metal beta-diketonate complexes. Its EINECS number is 221-875-7. This chemical's molecular formula is C10H14NiO4and molecular weight is 256.91. What's more, its systematic name is Bis(pentane-2,4-dionato-O,O')nickel. Its classification code is TSCA Flag P [A commenced PMN (Premanufacture Notice) substance]. This chemical is stable at common pressure and temperature, and it should be sealed and stored in a ventilated and dry place. Moreover, it should be protected from light. It is used as catalyst in organic reactions.
Physical properties of Nickel acetylacetonate are: (1)ACD/LogP: 0.289; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.29; (4)ACD/LogD (pH 7.4): 0.25; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 34.16; (8)ACD/KOC (pH 7.4): 31.16; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 37.3 Å2; (13)Flash Point: 71.9 °C; (14)Enthalpy of Vaporization: 49.32 kJ/mol; (15)Boiling Point: 187.6 °C at 760 mmHg; (16)Vapour Pressure: 0.174 mmHg at 25°C.
Preparation: this chemical can be prepared through the dehydration reaction and vacuum distillation of dihydrate nickel acetylacetonate or azeotropic distillation with toluene to get anhydrous nickel acetylacetonate.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It has a limited evidence of a carcinogenic effect. It may cause sensitisation by skin contact and cause cancer by inhalation. When using it, you need wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible). It should be avoided exposure, and you need to obtain special instructions before use.
You can still convert the following datas into molecular structure:
(1)SMILES: [Ni+2].O=C(/C=C(\[O-])C)C.[O-]\C(=C/C(=O)C)C
(2)Std. InChI: InChI=1S/2C5H8O2.Ni/c2*1-4(6)3-5(2)7;/h2*3,6H,1-2H3;/q;;+2/p-2/b2*4-3-;
(3)Std. InChIKey: BMGNSKKZFQMGDH-FDGPNNRMSA-L
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 125mg/kg (125mg/kg) | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 4, Pg. 231, 1952. |
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