Acetylacetone

Base Information

• Chemical Name: Acetylacetone
• CAS No.: 123-54-6
• Deprecated CAS: 81235-32-7
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 2914 19 90
• European Community (EC) Number: 204-634-0
• ICSC Number: 0533
• NSC Number: 5575
• UN Number: 2310
• UNII: 46R950BP4J
• DSSTox Substance ID: DTXSID4021979
• Nikkaji Number: J2.499F
• Wikipedia: Acetylacetone
• Wikidata: Q413447
• Metabolomics Workbench ID: 5472
• ChEMBL ID: CHEMBL191625
• Mol file: 123-54-6.mol

Synonyms:2,4-pentanedione;acetylacetone;indium-111-acetylacetone

Chemical Property of Acetylacetone

Chemical Property:

• Appearance/Colour: colorless or yellow colored liquid
• Vapor Pressure: 6 mm Hg ( 20 °C)
• Melting Point: -23 °C
• Refractive Index: n20/D 1.452(lit.)
• Boiling Point: 138.4 °C at 760 mmHg
• PKA: 8.9(at 25℃)
• Flash Point: 43.1 °C
• PSA: 34.14000
• Density: 0.95 g/cm³
• LogP: 0.55450
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble1 in 8 parts
• Water Solubility.: 16 g/100 mL (20 ºC)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 82.3
• Transport DOT Label: Flammable Liquid Poison

Purity/Quality:

97% ^*data from raw suppliers

Acetylacetone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 11-36/37/38-22-10-R22-R10-20/21/22-2017/10/22
• Safety Statements: 21-23-24/25-36-26-S24/25-S23-S21

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aliphatic Ketones, Other
• Canonical SMILES: CC(=O)CC(=O)C
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the nervous system. This may result in tissue lesions.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the thymus, lungs, central nervous system and nasal passage.
• Uses: 1. Pentanedione, also known as acetyl acetone, is the intermediates of fungicides such as methyl mepanipyrim, mepanipyrim and herbicide pyrazosulfuron-methyl. 2. It can be used as the raw material of pharmaceutical and organic intermediates, as well as solvent. 3. It can be used as a analysis reagent and the aluminum extraction agent from tungsten, molybdenum. 4. Acetylacetone 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. Acetylacetone 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, it is used for the antidiarrheal medicine and livestock feed additives in more than 50% of cases. 5. In addition to having the typical properties of alcohols and ketones, it can also exhibit dark red color together with iron dichloride, and form chelate with many kinds of salts. It is produced from the condensation reaction between acetic anhydride or acetyl chloride and acetone, or from the reaction between acetone and diketene. It can be used as metal extraction agent for separation of three or tetravalent ions; it can also be used as paints and inks desiccant, pesticides, fungicides, and the solvent of polymer; moreover, it can also used as reagents for determination of thallium, iron, fluorine and be used as the intermediates for organic synthesis. 6. It can be as a transition metal chelator. It can be used for measuring the content of iron and fluorine with colorimetric determination, or used for measuring thallium in the presence of carbon disulfide. 7. It is the indicator for Fe (III) complex titration; it can be used for modifying the guanidine groups and amino-groups inside a protein. Chemical intermediate, metal chelator, and lubricant additive Acetylacetone was used in preparing Y203, La203 and La2CuO4 thin films and the titanate/anatase dual-phase photocatalyst. Acetyl acetone is used as a reagent fororganic synthesis and as a transition metalchelating agent. Its organometallic complexes are used as additives for gasoline andlubricants, and in varnishes, color, ink, andfungicides. Forms organometallic complexes which are used as gasoline additives, lubricant additives, driers for varnishes and printer's inks, fungicides, insecticides, colors.
• Description: Acetylacetone (2,4-pentanedione) is a clear or slightly yellowish liquid with a putrid odour. It is readily soluble in water and in organic solvents and incompatible with light, ignition sources, excess heat, oxidising agents, strong reducing agents, and strong bases. On decomposition, acetylacetone releases hazardous products such as carbon monoxide, irritating and toxic fumes and gases, and carbon dioxide. Acetylacetone is used in the production of anti-corrosion agents and its peroxide compounds for the radical initiator application for polymerisation. It is used as a chemical intermediate for drugs (such as sulphamethazine, nicarbazine, vitamin B6, and vitamin K) and pesticides sulfonylurea herbicides and pesticides. It is used as an indicator for the complexometric titration of Fe (III), for the modification of guanidino groups and amino groups in proteins, and for the preparation of metal acetylacetonates for catalyst application.

Technology Process of Acetylacetone

There total 228 articles about Acetylacetone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 33.0%

acetylene (74-86-2,25067-58-7) → 1,3,5,7-cyclooctatetraene (629-20-9) + toluene (108-88-3,15644-74-3,16713-13-6) + acetylacetone (123-54-6,81235-32-7) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

bis(acetylacetonate)nickel(II); calcium carbide; In tetrahydrofuran; at 85 - 90 ℃; Further byproducts given;

DOI:10.1021/ja00278a017

Reference yield:

3-(4-Dimethylaminobenzyliden)-2,4-pentandion (63053-27-0) → 4-dimethylamino-benzaldehyde (100-10-7) + acetylacetone (123-54-6,81235-32-7)

Guidance literature:

With sodium hydroxide; water; In ethanol; at 25 ℃; Rate constant; alkaline hydrolysis;

Reference yield:

3-benzylidene acetylacetone (4335-90-4) → benzaldehyde (100-52-7) + acetylacetone (123-54-6,81235-32-7)

Guidance literature:

With water; at 25 ℃; Mechanism; Rate constant; Equilibrium constant; various pH (HCl or KOH solutions, acetate buffers; also with DABCO);

DOI:10.1021/jo00093a012

upstream raw materials:

7,9-diacetoxy-2,6-diacetyl-3-hydroxy-8,9b-dimethyl-4a,9b-dihydro-4H-dibenzofuran-1-one

Ketene

(1,3-dimethyl-butyl)-isopropyliden-amine

methyl magnesium iodide

Downstream raw materials:

4-(1-pyrrolidinyl)-3-penten-2-one

3,5-diacetyl-4-phenyl-2,6-heptadione

3-(α-piperidino-benzyl)-pentane-2,4-dione

3-benzylidene acetylacetone

Refernces

• 1、 Hass et al.. "-". . p. 952. Retrieved 1974.
• 2、 Hasek,R.H. et al.. "-". . p. 2513 - 2516. Retrieved 1964.
• 3、 Chaichi, Mohammad Javad,Ehsani, Mahjoobeh,Khajvand, Tahereh,Golchoubian, Hamid,Rezaee, Ehsan. "Determination of cysteine and glutathione based on the inhibition of the dinuclear Cu(II)-catalyzed luminol-H2O2 chemiluminescence reaction". . p. 405 - 410. Retrieved 2014.
• 4、 Krokhalev, V. M.,Saloutin, V. I.,Pashkevich, K. I.. "HYDROLYSIS OF FLUOROALKYL-CONTAINING β,β'-TRIKETONES". . p. 1956 - 1957. Retrieved 1988.
• 5、 Motoki,S.,Sato,T.. "-". . p. 1322 - 1324. Retrieved 1969.
• 6、 Kolos, Nadezhda N.,Karpan, Sergey A.,Omelchenko, Irina V.,Chechina, Natal’ya V.,Yaremenko, Feodor G.. "One-pot diastereoselective synthesis of functionalized 4,5-dihydropyrroles by reactions of arylglyoxals, β-dicarbonyl compounds, and aromatic amines". . p. 827 - 833. Retrieved 2019.
• 7、 v. Hoene et al.. "". . p. 1098,1099,1101. Retrieved 1958.
• 8、 Li, Yanfang,Liu, Yang,Zhou, Ming. "Acid induced acetylacetonato replacement in biscyclometalated iridium(III) complexes". . p. 3807 - 3816. Retrieved 2012.
• 9、 Schwarzenbach,Felder. "-". . p. 1701,1702. Retrieved 1944.
• 10、 Udagawa,Tomiyasu,Jung,Eom,Fukutomi. "Kinetics and mechanism of the substitution of β-diketonates for acetylacetonate in bis(acetylacetonato)(trimethyl phosphate)dioxouranium(VI)". . p. 2802 - 2806. Retrieved 1989.