2,5-Hexanedione

Base Information

• Chemical Name: 2,5-Hexanedione
• CAS No.: 110-13-4
• Molecular Formula: C6H10O2
• Molecular Weight: 114.144
• Hs Code.: 29141990
• European Community (EC) Number: 203-738-3
• NSC Number: 7621
• UN Number: 1224
• UNII: C0Z8884J3P
• DSSTox Substance ID: DTXSID8030138
• Nikkaji Number: J5.518B
• Wikipedia: Hexane-2,5-dione
• Wikidata: Q209264
• Metabolomics Workbench ID: 5478
• ChEMBL ID: CHEMBL1564795
• Mol file: 110-13-4.mol

Synonyms:1,2-diacetylethane;2,5-diketohexane;2,5-dioxohexane;2,5-hexanedione;acetone, acetonyl;acetonyl acetone;acetonylacetone;alpha, beta-diacetylethane;diacetonyl;hexanedione, 2,5-;NSC-7621

Chemical Property of 2,5-Hexanedione

Chemical Property:

• Appearance/Colour: clear slight brown liquid
• Vapor Pressure: 0.43 mm Hg ( 20 °C)
• Melting Point: -6―-5 °C(lit.)
• Refractive Index: n20/D 1.425(lit.)
• Boiling Point: 188.8 °C at 760 mmHg
• Flash Point: 78.9 °C
• PSA: 34.14000
• Density: 0.973 g/cm³
• LogP: 0.94460
• Storage Temp.: Store below +30°C.
• Solubility.: alcohol: miscible
• Water Solubility.: miscible
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 114.068079557
• Heavy Atom Count: 8
• Complexity: 91.1
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99.0%min ^*data from raw suppliers

Acan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn,Xi
• Statements: 36/38-48/20/21/22-36/37/38
• Safety Statements: 23-26-36/37-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Ketones (
• Canonical SMILES: CC(=O)CCC(=O)C
• Uses: It is the metabolite implicated in n-hexane neurotoxicity. 2,5-Hexanedione is used as a reagent in the preparation of trans-2,5-dimethylpyrrolidine. It is also used in the synthesis of 2,5-dimethylpyrroles. Further, it plays an important role as a reagent used for the protection of amino groups in amino sugars and nucleosides. In addition to this, it is used in the preparation of five-membered heterocycles like indane-type and benzannulated systems. It is also employed as a precursor in Diels-alder cycloaddition reactions. It was used as reference standard for the determination of 2,5HD in human urine using gas chromatography-electron capture detection and gas chromatography-mass selective detection.

Technology Process of 2,5-Hexanedione

There total 251 articles about 2,5-Hexanedione 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: 58.0%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) + formic acid (64-18-6) → 2,5-dimethyltetrahydrofuran (1003-38-9) + 2,5-dimethylfuran (625-86-5) + 2,5-bis-(hydroxymethyl)furan (1883-75-6) + 5-(2-furaldehyde)methyl formate (102390-86-3) + 2-(formyloxy)methyl-5-(hydroxymethyl)furan (1253934-87-0) + 2,5-hexanedione (110-13-4)

Guidance literature:

With gold nanoparticles anchored on tetragonal-phase zirconia; In toluene; at 140 ℃; for 0.5h; under 760.051 Torr; Solvent; Inert atmosphere;

DOI:10.1016/j.chempr.2018.07.007

Reference yield: 16.0%

acetylacetone (123-54-6,81235-32-7) → LACTIC ACID (849585-22-4,106989-11-1,26811-96-1,31587-11-8,26100-51-6) + 2-acetoxypropionic acid (535-17-1) + Ethylene glycol di-tert-butyl diether (26547-47-7) + 3-acetoxy-3-methylbutanoic acid (44983-17-7) + 2,5-hexanedione (110-13-4) + D,L-lactide (95-96-5,26680-10-4,26969-66-4,615-95-2)

Guidance literature:

With dihydrogen peroxide; In tert-butyl alcohol; for 36h; Reflux;

DOI:10.1007/s11172-013-0316-6

Reference yield: 14.0%

2,5-dimethylfuran (625-86-5) → 2,5-dimethyltetrahydrofuran (1003-38-9) + 2,5-hexanedione (110-13-4)

Guidance literature:

With 5 wt% ruthenium/carbon; sulfuric acid; isopropyl alcohol; In water; at 80 ℃; for 2h; Sealed tube; Inert atmosphere;

DOI:10.1016/j.apcata.2017.06.010

upstream raw materials:

2,5-dimethylfuran

4-acetyl-2-methyl-5-oxo-tetrahydro-furan-2-carbonitrile

1-methyl-4-nitrosobenzene

2,5-dimethyl-1,5-hexadiene

Downstream raw materials:

4,7-dimethyl-2-phenyl-indole

N-(2,5-dimethyl-1H-pyrrol-1-yl)furan-2-carboxamide

8-(2,5-dimethyl-1H-pyrrol-1-yl)quinoline

1-(1-hydroxy-1,4,8b-trimethyl-1,2,3,3a,4,8b-hexahydro-cyclopent[b]indol-3-yl)-ethanone

Refernces

• 1、 Strachan,Blacet. "-". . p. 5254. Retrieved 1955.
• 2、 Bloodworth, A. J.,Baker, David S.. "Dehydrogenation of Cyclic and Bicyclic Secondary Alkyl Peroxides during Flash Vacuum Pyrolysis". . p. 547 - 549. Retrieved 1981.
• 3、 Luijkx, Gerard C.A.,Huck, Nina P.M.,Van Rantwijk, Fred,Maat, Leendert,Van Bekkum, Herman. "Ether formation in the hydrogenolysis of hydroxymethylfurfural over palladium catalysts in alcoholic solution". . p. 1037 - 1044. Retrieved 2009.
• 4、 Gagnon, Janet L.,Zajac Jr., Walter W.. "Oxidative cleavage of cis-1,2-diamino-1,2-dimethylcyclobutane to 2,5-hexanedione". . p. 1803 - 1804. Retrieved 1995.
• 5、 Farlow et al.. "-". . p. 2498. Retrieved 1934.
• 6、 Dai, Yiying,Liu, Qing,Liu, Yakun,Liu, Yanan,Ma, Chi,Nie, Genkuo,Pan, Lun,Shi, Chengxiang,Zhang, Xiangwen,Zou, Ji-Jun. "Producing methylcyclopentadiene dimer and trimer based high-performance jet fuels using 5-methyl furfural". . p. 7765 - 7768. Retrieved 2020.
• 7、 Ficini,J.,Genet,J.-P.. "-". . p. 1565 - 1567. Retrieved 1971.
• 8、 Kosugi, Masanori,Ohashi, Kenji,Akuzawa, Kazuko,Kawazoe, Takashi,Sano, Hiroshi,Migita, Toshihoko. "2-Ethoxy-2-propenyl Diethyl Phosphate. An Efficient Halo Acetone Equivalent for the Pd-Catalyzed Cross-coupling with Tin Enolates". . p. 1237 - 1238. Retrieved 1987.
• 9、 Markov, Peter,Petkov, Ivan,Roumian, Christian. "On the Photochemical Behaviour of Ethyl Acetoacetate in Water". . p. 1005 - 1008. Retrieved 1983.
• 10、 Polonowky. "-". . p. 24. Retrieved 1888.