14024-48-7

Basic information

• Product Name: Bis(acetylacetonato)cobalt
• Synonyms: TRIS(ACETYLACETONATO)COBALT(III);TRIS(2,4-PENTANEDIONATO)COBALT;TRIS(2,4-PENTANEDIONATO)COBALT(III);TRIS(2,4-PENTANEDIONATO)COBALT(3);4-pentanedionato-o,o’)-bis((beta-4)-cobal;Acetylacetone cobalt(II);Bis(2,4-pentanedionato)cobalt;bis(2,4-pentanedionato-O,O’)-,(T-4)-Cobalt
• CAS NO: 14024-48-7
• Molecular Formula: 2C₅H₇O₂*Co
• Molecular Weight: 356.26
• EINECS: 244-527-6
• Product Categories: Pharmaceutical Intermediates;Classes of Metal Compounds;Co (Cobalt) Compounds;Transition Metal Compounds
• Mol File: 14024-48-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 210-213 °C(lit.)
• Boiling Point: 138.4ºC at 760mmHg
• Flash Point: 43.1ºC
• Appearance: Purple/Fine Crystalline Powder
• Density: 0.83 g/cm3 (20℃)
• Vapor Pressure: 0.174mmHg at 25°C
• Storage Temp.: Store below +30°C.
• Solubility: 5.1g/l
• Water Solubility: 5 g/L (20 ºC)
• Sensitive: Hygroscopic
• CAS DataBase Reference: Bis(acetylacetonato)cobalt(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(acetylacetonato)cobalt(14024-48-7)
• EPA Substance Registry System: Bis(acetylacetonato)cobalt(14024-48-7)

Safety Data

• Hazard Codes: Xn
• Statements: 42/43-40-22-41-20/21/22
• Safety Statements: 22-36/37-45-24-37/39-26-7
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• F: 21
• TSCA: Yes
• Hazardous Substances Data: 14024-48-7(Hazardous Substances Data)

Usage

Description

Bis (acetylacetonato) cobalt (also known as Cobalt (II) acetylacetonate) is used as an important catalyst for organic reactions. It can also be used as paint dryer1. The cobalt (II) acetylacetonate complex immobilized on aminosilane-modified SBA-15 can act as an efficient catalyst for epoxidation of trans-stilbene with molecular oxygen2. Cobalt (II) Acetylacetonate is a cobalt source that is soluble in organic solvents as an organometallic compound (also known as metalorganic, organo-inorganic and metallo-organic compounds). The high purity acetylacetonate anion complexes by bonding each oxygen atom to the metallic cation to form a chelate ring; because of this property, acetylacetonates are commonly used in various catalysts and catalytic reagents for organic synthesis, including the fabrication of various shapes of carbon nanostructures (as demonstrated by a 2013 experiment by researchers at the Leibniz Institute for Solid State and Materials Research Dresden) via the use of chemical vapor deposition (CVD) and laser evaporation techniques3.

References

https://www.alfa.com/en/catalog/012537/ https://onlinelibrary.wiley.com/doi/abs/10.1002/aoc.3451 https://www.americanelements.com/cobalt-ii-acetylacetonate-14024-48-7

Chemical Properties

PURPLE FINE CRYSTALLINE POWDER

Uses

Cobalt(II) 2,4-pentanedionate is used as an important catalyst for organic reactions. It is also used as paint dryer.

Flammability and Explosibility

Nonflammable

Purification Methods

Recrystallise it from acetone or MeOH and dry it in a vacuum. [Beilstein 1 H 783.]

InChI:InChI=1/2C5H8O2.Co/c2*1-4(6)3-5(2)7;/h2*3,6H,1-2H3;/q;;+2/p-2/b4-3+;4-3-;

Synthetic route

bis(acetylacetonato)cobalt(II) (14024-48-7) + Bromodiphenylmethane (776-74-9) → 3-benzhydryl-pentane-2,4-dione (19672-37-8)

Conditions	Yield
In chloroform for 17h; Heating;	97%

3-bromo-5-methylcyclohex-1-ene (872290-35-2) + bis(acetylacetonato)cobalt(II) (14024-48-7) → 3-(5-methyl-2-cyclohexenyl)pentane-2,4-dione

Conditions	Yield
In chloroform at 85℃; for 2h;	95%

p-Methoxybenzyl bromide (2746-25-0) + bis(acetylacetonato)cobalt(II) (14024-48-7) → 3<(p-methoxyphenyl)methyl>-2,4-pentanedione (30881-24-4)

Conditions	Yield
In chloroform for 17h; Heating;	88%

1-Adamantyl bromide (768-90-1) + bis(acetylacetonato)cobalt(II) (14024-48-7) → 3-(adamantan-1-yl)pentane-2,4-dione (102402-84-6)

Conditions	Yield
In chlorobenzene for 24h; Heating;	81%
In chloroform at 80℃; for 17h;	76%

bis(acetylacetonato)cobalt(II) (14024-48-7) + (1-bromoethyl)benzne (585-71-7, 38661-81-3) → 3-(1-phenyl-ethyl)-pentane-2,4-dione (5186-08-3)

Conditions	Yield
In chloroform for 17h; Heating;	75%

5-methylcyclohex-2-enyl chloride (7318-66-3) + bis(acetylacetonato)cobalt(II) (14024-48-7) → 3-(5-methyl-2-cyclohexenyl)pentane-2,4-dione

Conditions	Yield
In chloroform at 120℃; for 2h;	71%

bis(acetylacetonato)cobalt(II) (14024-48-7) + (1-bromoethyl)benzne (585-71-7, 38661-81-3) → 2,3-diphenylbutane (1857-74-5, 2726-21-8, 4539-34-8, 4613-11-0, 71606-46-7, 5789-35-5) + 3-(1-phenyl-ethyl)-pentane-2,4-dione (5186-08-3)

Conditions	Yield
In chloroform at 80℃; for 1h;	A 21% B 54%

bis(acetylacetonato)cobalt(II) (14024-48-7) + (1-bromoethyl)benzne (585-71-7, 38661-81-3) → 2,3-diphenylbutane (1857-74-5, 2726-21-8, 4539-34-8, 4613-11-0, 71606-46-7, 5789-35-5) + 3-(1-phenyl-ethyl)-pentane-2,4-dione (5186-08-3) + CoBr2

Conditions	Yield
In chloroform at 80℃; for 1h; Product distribution; Mechanism; other halogenides;	A 21% B 54% C n/a

benzyl bromide (100-39-0) + bis(acetylacetonato)cobalt(II) (14024-48-7) → 3-benzyl-pentane-2,4-dione (1134-87-8) + 3,3-dibenzyl-pentane-2,4-dione (53316-00-0)

Conditions	Yield
In chloroform at 120℃; for 1h;	A 51% B 15%

(1-chlorohex-5-en-1-yl)benzene (61608-88-6) + bis(acetylacetonato)cobalt(II) (14024-48-7) → (E)-1-phenyl-1,5-hexadiene (56644-04-3) + 3-(1-phenyl-5-hexen-1-yl)pentane-2,4-dione + 1-chloro-3-phenylcyclohexane

Conditions	Yield
In chloroform at 100℃; for 17h;	A 46% B 10% C 42%

bis(acetylacetonato)cobalt(II) (14024-48-7) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 3-(4-nitrobenzyl)-2,4-pentanedione (56699-21-9)

Conditions	Yield
In chloroform for 17h; Heating;	6%

N-m-Tolyl-aminophthalimid (4870-21-7) + bis(acetylacetonato)cobalt(II) (14024-48-7) → C12H14NO3 (120722-86-3)

Conditions	Yield
With methanol; tert.-butylhydroperoxide benzene; Multistep reaction;

2-<(4-Methoxyphenyl)amino>-1H-isoindol-1,3-(2H)-dion (107940-72-7) + bis(acetylacetonato)cobalt(II) (14024-48-7) → C12H14NO4 (120722-88-5)

Conditions	Yield
With methanol; tert.-butylhydroperoxide benzene; Multistep reaction;

N-anilinophthalimide (4870-16-0) + bis(acetylacetonato)cobalt(II) (14024-48-7) → 3-ethylidene-pentane-2,4-dione (15181-39-2, 67556-21-2, 67556-22-3) + C11H12NO3 (120722-83-0)

Conditions	Yield
With methanol; tert.-butylhydroperoxide benzene; Yield given. Multistep reaction;
With methanol; tert.-butylhydroperoxide benzene; Multistep reaction. Title compound not separated from byproducts;

2-p-toluidino-isoindoline-1,3-dione (4870-23-9) + bis(acetylacetonato)cobalt(II) (14024-48-7) → C12H14NO3 (120722-84-1)

Conditions	Yield
With methanol; tert.-butylhydroperoxide benzene; Multistep reaction;

5-methylcyclohex-2-enyl chloride (7318-66-3) + bis(acetylacetonato)cobalt(II) (14024-48-7) → trans-3-(5-methyl-2-cyclohexenyl)pentane-2,4-dione + cis-3-(5-methyl-2-cyclohexenyl)pentane-2,4-dione

Conditions	Yield
In chloroform at 120℃; for 2h; Product distribution; Mechanism; other halogenides, regioselectivity, stereoselectivity;

N-(N-4-chlorophenylamino)phthalimide (107940-74-9) + bis(acetylacetonato)cobalt(II) (14024-48-7) → C11H11ClNO3 (120722-87-4)

Conditions	Yield
With methanol; tert.-butylhydroperoxide benzene; Multistep reaction;

1-(4-chlorophenyl)-3-(4-nitrophenyl)-2-propen-1-ol (39212-17-4) + bis(acetylacetonato)cobalt(II) (14024-48-7) → 3-(3-(4-chlorophenyl)-1-(4-nitrophenyl)-2-propenyl)pentane-2,4-dione + 3-(1-(4-chlorophenyl)-3-(4-nitrophenyl)-2-propenyl)pentane-2,4-dione

Conditions	Yield
With thionyl chloride 1) room temperature, 6 h, 2) CHCl3, 100 deg C, 24 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

2-<(4-Nitrophenyl)amino>-1H-isoindol-1,3(2H)-dion (100873-75-4) + bis(acetylacetonato)cobalt(II) (14024-48-7) → C11H11N2O5 (120722-89-6)

Conditions	Yield
With methanol; tert.-butylhydroperoxide benzene; Multistep reaction;

bis(acetylacetonato)cobalt(II) (14024-48-7) + 2-<(2-Methoxyphenyl)amino>-1H-isoindol-1,3-(2H)-dion (117359-11-2) → C12H14NO4 (120722-90-9)

Conditions	Yield
With methanol; tert.-butylhydroperoxide benzene; Multistep reaction;

bis(acetylacetonato)cobalt(II) (14024-48-7) + (1-chloroethyl)benzene (672-65-1) → 2,3-diphenylbutane (1857-74-5, 2726-21-8, 4539-34-8, 4613-11-0, 71606-46-7, 5789-35-5) + 3-(1-phenyl-ethyl)-pentane-2,4-dione (5186-08-3)

Conditions	Yield
In chloroform at 80℃; for 6.25h; Yield given. Yields of byproduct given;

Downstream Products

• 102402-84-6 3-(adamantan-1-yl)pentane-2,4-dione 
• 120722-88-5 C₁₂H₁₄NO₄ 
• 120722-87-4 C₁₁H₁₁ClNO₃ 
• 120722-89-6 C₁₁H₁₁N₂O₅ 
• 1857-74-5 2,3-diphenylbutane 
• 5186-08-3 3-(1-phenyl-ethyl)-pentane-2,4-dione 
• 19672-37-8 3-benzhydryl-pentane-2,4-dione 
• 56699-21-9 3-(4-nitrobenzyl)pentane-2,4-dione 
• 120722-90-9 C₁₂H₁₄NO₄ 
• 30881-24-4 3<(p-methoxyphenyl)methyl>-2,4-pentanedione 
• 1134-87-8 3-benzyl-pentane-2,4-dione 
• 53316-00-0 3,3-dibenzyl-pentane-2,4-dione 
• 120722-84-1 C₁₂H₁₄NO₃ 
• 56644-04-3 (E)-1-phenyl-1,5-hexadiene 

Relevant articles and documents

Ethylene dimerization

An ethylene dimerization process is provided wherein ethylene is contacted with an organocobalt(II) or organocobalt(III) compound and a borohydride compound in a solvent to produce a product reaction mixture comprising a C4 fraction of predominantly 1-butene. A phosphine compound can additionally be provided in the solvent with an organocobalt(III) compound to enhance selectivity to 1-butene.