ACETYL ACETONE

Acetyl acetone is also one of the simplest saturated β-diketones and is a derivative of acetone. 
Acetyl acetone has an active chemical property and can react with ferric chloride aqueous solution to exhibit a dark red color. 
Acetyl acetone can almost react with the hydroxides, carbonates or acetates of all metals to form a complex with a general formula being (C5H7O2) • M, wherein M corresponds to the metal element and n is the metal compounds. 

CAS Number: 123-54-6
Molecular Formula: C5H8O2
Molecular Weight: 100.12
EINECS Number: 204-634-0

Synonyms: Acetylacetone, 2,4-Pentanedione, Pentane-2,4-dione, 123-54-6, Acetoacetone, ACAC, 2,4-Dioxopentane, Diacetylmethane, 2,4-Pentadione, ACETYL ACETONE, Pentanedione, Pentan-2,4-dione, Pentanedione-2,4, Acetyl 2-propanone, Acetone, acetyl-, Hacac, 2-Propanone, acetyl-, 2,4-Pentandione, NSC 5575, acetylaceton, CCRIS 3466, acetyl-acetone, HSDB 2064, EINECS 204-634-0, 4-Hydroxy-3-penten-2-one, UNII-46R950BP4J, BRN 0741937, CH3-CO-CH2-CO-CH3, DTXSID4021979, CHEBI:14750, AI3-02266, 46R950BP4J, ACETYLACETONE ENOL, CH3COCH2COCH3, NSC-5575, MFCD00008787, DTXCID601979, EC 204-634-0, 4-01-00-03662 (Beilstein Handbook Reference), 14024-62-5, UN2310, Acetylaceetone, 81235-32-7, pentane-2, pentan-2, acetylacetone (2,4-pentanedione), 2,4 pentanedione, 2.4-pentanedione, pentane2,4-dione, Acetyl-2-Propanone, Acetyl-2-propaneone, 2,4-pentane-dione, ACETYLACETONE [MI], 1-methylbutane-1,3-dione, SCHEMBL1608, NCIOpen2_000702, Pentane-2,4-dione [UN2310] [Flammable liquid], ACETYL ACETONE [HSDB], CHEMBL191625, WLN: 1V1V1, Acetylacetone;Pentane-2,4-dione, BDBM22766, NSC5575, Acetylacetone, analytical standard, BCP31333, STR00020, Tox21_200414, LMFA12000075, AKOS000118994, UN 2310, Acetylacetone, ReagentPlus(R), >=99%, NCGC00248599-01, NCGC00257968-01, BP-30252, CAS-123-54-6, PD193123, Acetylacetone, JIS special grade, >=99%, DB-020012, DB-318551, DS-002710, NS00007112, P0052, EN300-19143, Q413447, Pentane-2,4-dione [UN2310] [Flammable liquid], F1908-0168, InChI=1/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H, Acetylacetone, produced by Wacker Chemie AG, Burghausen, Germany, >=99.5% (GC), acetyl;Acetyl 2-propanone;acetyl-2-propanon;acetyl2-propanone;acetyl-aceton;CH3COCH2COCH3;pentan-2,4-dione;Pentanedione

Acetyl acetone is a derivative of acetone; chemical formula: CH3COCH2COCH3; It is colorless to pale yellow transparent liquid. 
Acetyl acetone is usually the mixture is enol form and keto form which are the tautomers of each other; these two forms are in dynamic equilibrium; enol isomer forms hydrogen bonds inside the molecule; in the mixture, the keto form accounts for about 18% and enol type accounted for 82%. 
Cool the petroleum ether of their mixture to-78 °C so the enol will be precipitated as a solid and the two forms will be separated with each other. 

Upon the enol form being returned back to room temperature, the above equilibrium will be restored.
Acetyl acetone, also known as 2,4-Pentanedione, is an organic compound with the chemical formula C₅H₈O₂. 
It is a colorless or slightly yellow liquid that exhibits a characteristic odor and is known for its ability to exist in two tautomeric forms: the keto form and the enol form.

This compound is widely used as a precursor, ligand, and reagent in various chemical reactions, particularly in coordination chemistry, where it forms stable metal chelates with many metal ions. 
Due to its ability to act as both an acid and a base, acetylacetone is also an essential component in organic synthesis, acting as a building block for pharmaceuticals, agrochemicals, and polymer production. 
Additionally, it serves as a solvent and stabilizer in certain industrial applications, including paint and coating formulations. 

Acetyl acetone is also a flammable liquid and should be handled with caution, as prolonged exposure may cause irritation to the skin, eyes, and respiratory system.
Acetyl acetone have a pleasant odor. 
It is flammable, and has a relative molecular mass of 100.13. 

Acetyl acetones relative density is 0.9721 (25 °C). 
Its melting point is-23.5 °C and boiling point is 140.5 °C or 139 °C (99.458 × 103Pa). 
Its flash point is 41 °C. 

Acetyl acetone has a vapor pressure of 0.800 × 103Pa (20 °C), (At 20 °C 16.9,80 °C at 34) and is soluble in water, ethanol, benzene, chloroform, ether, acetone, ethyl acetate and acetic acid. 
Acetyl acetone is susceptible to hydrolysis to generate acetic acid and acetone. 
The molecular structure of the acetylacetone is a saturated diketone structure in which two hydroxyl groups are connected by a methylene group; this form is usually referred to as β-diketone. 

Most of such compounds are stable, and many of them are soluble in many organic solvents.
Acetyl acetone can have reaction with chlorine in the presence of light of with only two ends of methyl hydrogen being replaced by chlorine. 
When Acetyl acetone is reacted with sodium, it can release hydrogen and generates sodium acetylacetonate. 

Acetyl acetone have a narcotic effect and can stimulate the skin and mucous membranes; at high concentrations (100 × 10-6 or more), it is easy to produce some symptoms of poisoning such as nausea, headache, and dizziness.
Acetyl acetone is an organic compound with the chemical formula CH3−C(=O)−CH2−C(=O)−CH3. 
Acetyl acetone is classified as a 1,3-diketone. 

Acetyl acetone exists in equilibrium with a tautomer CH3−C(=O)−CH=C(−OH)−CH3. 
The mixture is a colorless liquid. 
These tautomers interconvert so rapidly under most conditions that they are treated as a single compound in most applications.

Acetyl acetone is a building block for the synthesis of many coordination complexes as well as heterocyclic compounds.
The keto and enol tautomers of acetylacetone coexist in solution. 
The enol form has C2v symmetry, meaning the hydrogen atom is shared equally between the two oxygen atoms.

In the gas phase, the equilibrium constant, Kketo→enol, is 11.7, favoring the enol form. 
The two tautomeric forms can be distinguished by NMR spectroscopy, IR spectroscopy and other methods.
The equilibrium constant tends to be high in nonpolar solvents; when Kketo→enol is equal or greater than 1, the enol form is favoured. 

The keto form becomes more favourable in polar, hydrogen-bonding solvents, such as water.
The enol form is a vinylogous analogue of a carboxylic acid.
Acetyl acetone, Na(acac), is the precursor to many acetylacetonate complexes. 

A general method of synthesis is to treat a metal salt with acetylacetone in the presence of a base: MBz + z Hacac ⇌ M(acac)z + z BH
Both oxygen atoms bind to the metal to form a six-membered chelate ring.
In some cases the chelate effect is so strong that no added base is needed to form the complex.

Acetyl acetone, also referred to as 2,4-Pentanedione, is a diketone compound that plays a crucial role in various chemical and industrial applications due to its unique structural properties. 
Acetyl acetone is a volatile, flammable liquid with a mild yet distinct odor, and it readily participates in tautomerism, meaning it can exist in two interchangeable forms: the keto form (which contains two carbonyl groups) and the enol form (which features a hydroxyl group attached to a carbon-carbon double bond). 
This enol-keto equilibrium makes acetylacetone a particularly valuable compound in coordination chemistry, where it acts as a bidentate ligand to form stable metal chelates, particularly with transition metals such as copper, nickel, and aluminum.

Melting point: -23 °C (lit.)
Boiling point: 140.4 °C (lit.)
Density    0.975 g/mL at 25 °C (lit.)
vapor density: 3.5 (vs air)
vapor pressure: 6 mm Hg ( 20 °C)
refractive index: n20/D 1.452(lit.)
Flash point: 66 °F
storage temp.: Store below +30°C.
solubility: H2O: soluble1 in 8 parts
pka: 8.9(at 25℃)
form: Liquid
color: very deep green-yellow
Relative polarity: 0.571
PH: 6 (200g/l, H2O, 20℃)
Odor: pleasant odor
Evaporation Rate: 0.75
Relative density, gas (air=1): 3.5
explosive limit: 2.4-11.4%(V)
Water Solubility: 16 g/100 mL (20 ºC)
Merck: 14,81
BRN: 741937
Exposure limits    No exposure limit has been set.
Dielectric constant: 23.1（20℃）
InChIKey: YRKCREAYFQTBPV-UHFFFAOYSA-N
LogP: 0.68 at 20℃

Acetyl acetone presents certain hazards. 
It is a highly flammable liquid that can ignite easily under heat or open flames, posing a fire risk in laboratory and industrial settings. 
Moreover, exposure to Acetyl acetone can cause irritation to the skin, eyes, and respiratory tract, and prolonged inhalation of its vapors may result in dizziness, headaches, or more severe toxic effects on the central nervous system. 

As a result, Acetyl acetone must be handled with appropriate safety precautions, such as using protective gloves, goggles, and working in well-ventilated areas or fume hoods.
Acetyl acetone is an important intermediate for organic synthesis which is widely used in pharmaceutical, perfume, pesticides and other industries.
Acetyl acetone is an important raw material in the pharmaceutical industry, such as for the synthesis of 4,6-dimethyl-pyrimidine derivatives. 

Acetyl acetone can also be used as the solvents for cellulose acetate, the drying agent for paints and varnishes, etc., and are also important analytical reagents.
Due to the presence of enol, acetylacetone can form chelate with a variety of metals such as cobalt (II), Co (III), beryllium, aluminum, and chromium, iron (II), copper, nickel, palladium, zinc, indium, tin, zirconium, magnesium, manganese, scandium and thorium; it can also be used as fuel additives and lubricant additives.
Taking advantage of its chelation reaction with many kinds of metals, it can be used as a kind of metal cleaning agent for micropore.

Acetyl acetone can also used as a catalyst, a resin cross-linking agent, the resin curing accelerator; resins, rubber additives; for the hydroxylation reaction, hydrogenation reaction, isomerized reaction, and the synthesis of low molecular weight unsaturated ketone as well as polymerization and copolymerization of low-carbon olefins; it can also be used as an organic solvent for dissolving cellulose acetate, ink, and paint.
Acetyl acetone can also used as paint drying agent; it can also be used as the raw materials for preparation of insecticide, fungicide materials, and animals laxatives as well as feed additives; it can also be used as infrared reflective glass, a transparent conductive film (indium salt), a superconducting thin film (indium salt) forming agent; acetylacetone metal complexes has special colors (green copper salts, iron red, purple chromium salt) and is insoluble in water; it can also be used as pharmaceutical raw materials and raw materials for organic synthesis.

Moderate toxicity, can stimulate skin and mucous membrane. 
If the human body stays at 150 ~ 300mg/kg for a long time, it will have symptoms such as headache, nausea, vomiting, vertigo and sensory retardation.
In the Acetyl acetone anion, both C-O bonds are equivalent. 

Both C-C central bonds are equivalent as well, with one hydrogen atom bonded to the central carbon atom (the C3 atom). 
Those two equivalencies are because there is a resonance between the four bonds in the O-C2-C3-C4-O linkage in the acetylacetonate anion, where the bond order of those four bonds is about 1.5. 
Both oxygen atoms equally share the negative charge. 

The Acetyl acetone anion is a bidentate ligand.
Acetyl acetone is a versatile bifunctional precursor to heterocycles because both keto groups may undergo condensation. 
For example, condensation with hydrazine produces pyrazoles while condensation with urea provides pyrimidines. 

Condensation with two aryl- or alkylamines gives NacNacs, wherein the oxygen atoms in Acetyl acetone are replaced by NR (R = aryl, alkyl).
Acetyl acetone is frequently employed as an intermediate in organic synthesis, helping to create pharmaceuticals, agrochemicals, dyes, and polymer precursors. 

Its ability to donate protons makes it an effective reagent in various condensation and alkylation reactions, enabling the production of a wide range of chemical derivatives.
Additionally, it serves as a solvent, stabilizer, and corrosion inhibitor in industrial applications, including in paints, coatings, and fuel additives.

Uses Of Acetyl acetone:
Pentanedione, also known as Acetyl acetone, is the intermediates of fungicides such as methyl mepanipyrim, mepanipyrim and herbicide pyrazosulfuron-methyl. 
It can be used as a analysis reagent and the aluminum extraction agent from tungsten, molybdenum. 
Acetyl acetone is a kind of intermediate of organic synthesis which produces amino-4,6-dimethyl-pyrimidine with guanidine; it is an important pharmaceutical raw materials. 

It can be used as the solvent for cellulose acetate, as gasoline and lubricant additives, as desiccants of paints and varnishes, and as fungicides as well as insecticides.
Acetyl acetone can also serve as a catalyst for cracking petroleum, hydrogenation and hydroformylation reactions as well as being the oxidation promoting agent of oxygen. 
It can be used to remove the metal oxides in porous solid and used for processing polypropylene. 

In the United States and Europe, Acetyl acetone is used for the antidiarrheal medicine and livestock feed additives in more than 50% of cases.
Acetyl acetone is used in the following products: coating products, non-metal-surface treatment products and inks and toners.
Other release to the environment of Acetyl acetone is likely to occur from: indoor use as processing aid and outdoor use as processing aid.

Other release to the environment of Acetyl acetone is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Acetyl acetone is used in the following products: coating products, laboratory chemicals, adhesives and sealants and fillers, putties, plasters, modelling clay. 

Acetyl acetone is used in the following areas: building & construction work and scientific research and development. 
Acetyl acetone is used for the manufacture of: machinery and vehicles and furniture. Other release to the environment of this substance is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use and indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters).

Acetyl acetone is used in the following products: coating products, adhesives and sealants, fillers, putties, plasters, modelling clay and polymers.
Release to the environment of Acetyl acetone can occur from industrial use: formulation of mixtures.
Acetyl acetone is used in the following products: coating products, polymers, adhesives and sealants, fillers, putties, plasters, modelling clay and laboratory chemicals.

Acetyl acetone has an industrial use resulting in manufacture of another substance (use of intermediates).
Acetyl acetone is used in the following areas: formulation of mixtures and/or re-packaging and offshore mining.
Acetyl acetone is used for the manufacture of: chemicals, machinery and vehicles, furniture and food products.

Release to the environment of Acetyl acetone can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites, as processing aid and as processing aid.
Acetyl acetone has a wide range of applications across various scientific, industrial, and commercial fields due to its unique chemical properties, particularly its ability to exist in equilibrium between its keto and enol forms. 
This property makes it highly reactive and useful in numerous chemical reactions.

One of its most significant uses is in coordination chemistry, where it serves as a bidentate ligand that can form stable metal chelates with transition metals such as copper, nickel, cobalt, and aluminum. 
These metal-acetylacetonate complexes are widely used as catalysts in chemical reactions, precursors for material synthesis, and in the production of specialty coatings, pigments, and dyes. 
Additionally, these chelates are important in analytical chemistry for detecting and quantifying metal ions in various samples.

Acetyl acetone is also an important intermediate in organic synthesis, where it participates in numerous condensation and alkylation reactions. 
It is commonly used in the production of pharmaceuticals, agrochemicals, and fine chemicals, including the synthesis of heterocyclic compounds, antibiotics, and fungicides. 
Because of its ability to stabilize free radicals and reactive intermediates, it plays a key role in polymer chemistry, helping to create high-performance polymers and resins used in adhesives, sealants, and coatings.

In the industrial sector, Acetyl acetone functions as a solvent and stabilizer in various formulations. 
It is often added to fuels, lubricants, and hydraulic fluids to prevent oxidation and degradation, thereby enhancing their stability and performance. 
It also acts as a corrosion inhibitor, protecting metal surfaces from rust and chemical damage, which is especially useful in the aerospace, automotive, and manufacturing industries.

Acetyl acetone is utilized in the production of specialty coatings and varnishes, where it improves adhesion, durability, and resistance to environmental factors. 
Its ability to modify surface properties makes it valuable in the creation of advanced materials, including heat-resistant paints and protective layers used in electronics and industrial equipment.

Acetyl acetone must be handled with care due to its flammability and potential health hazards. 
Proper storage and safety measures are necessary to ensure its safe use in laboratory, commercial, and industrial settings.

Safety Profile Of Acetyl acetone:
Acetyl acetone, while highly useful in various applications, poses several hazards that require careful handling and safety precautions.
Acetylacetone is highly flammable and can easily catch fire when exposed to heat, sparks, or flames. 
It should be stored away from sources of ignition, and proper precautions should be taken to prevent accidental fires.

Acetyl acetone can cause irritation to the skin, eyes, and respiratory system. 
Prolonged or repeated exposure may lead to more severe health effects, including:
Contact with Acetyl acetone can cause mild to moderate irritation, and prolonged exposure may lead to dermatitis or other skin conditions.

Direct contact with Acetyl acetone may cause irritation, redness, and discomfort. 
If splashed into the eyes, it can lead to severe irritation or even injury.

Breathing in Acetyl acetone vapors or fumes can irritate the nose, throat, and respiratory tract. 
Prolonged inhalation of high concentrations may cause dizziness, headaches, and nausea, and in extreme cases, it could damage lung tissue.