4-hydroxy-4-methyl-2-pentanone

Compound Structure:

Synonyms:

Diacetone alcohol; 4-HYDROXY-4-METHYL-2-PENTANONE;123-42-2;4-Hydroxy-4-methylpentan-2-one;Diacetonalkohol;Diketone alcohol;Diacetone;Pyranton;Tyranton; Acetonyldimethylcarbinol; Diacetone-alcool;Pyranton A

Compound ID:

NMPC-416

PubChem ID:

31256

Molecular Formula:

C6H12O2

Canonical SMILES:

CC(=O)CC(C)(C)O

InChIKey:

SWXVUIWOUIDPGS-UHFFFAOYSA-N

About the compound:

Diacetone alcohol (DAA), a clear, scent-free chemical with the structure CH₃C(O)CH₂C(OH)(CH₃)₂, is notable for its utility both as a versatile synthetic intermediary in chemical synthesis and as a solvent for various uses[1]. It possesses a chemical composition of C₆H₁₂O₂ and a molecular weight of 116.160 g/mol, featuring moderate water solubility and compatibility with numerous organic solvents. DAA's physical characteristics include a low freezing point of −47°C, a boiling point of 166°C, and it is classified as flammable with a flash point of 52°C. Produced via the Ba(OH)₂-catalyzed joining of two acetone molecules, a process originally described by Heintz, DAA can be dehydrated to form mesityl oxide, a type of α,β-unsaturated ketone. Its hydrogenation results in hexylene glycol, and reacting DAA with urea creates a heterocyclic compound known as diacetone-monourea[1].DAA finds application in numerous fields, notably in the production of cellulose ester lacquers, where its absence of odor is particularly appreciated, and in thinners, dopes, wood stains, and wood preservatives. It is further utilized in the manufacture of synthetic silk and leather, celluloid cements, and in the composition of hydraulic brake fluids when blended with castor oil in equal parts[1]. Separately, the study of polyvinyl alcohol (PVA)-based solid polymer electrolytes (SPEs) is relevant to the development of renewable energy and advanced energy storage solutions. Supercapacitors, recognized for their broad application potential in devices such as electric vehicles, encounter energy storage limitations that PVA-based SPEs seek to overcome. By employing PVA as the foundational polymer, these SPEs have demonstrated capabilities to boost the electrochemical performance of energy storage systems through improved ionic conductivity[2].

References

1. Wikipedia contributors. "Diacetone Alcohol." Wikipedia, The Free Encyclopedia. https://en.wikipedia.org/w/index.php?title=Diacetone_alcohol&oldid=1153193835.

2. Danbature, W. L., Abdulkadir, B. A., et al. "A Review of Current Trends on Polyvinyl Alcohol (PVA)-Based Solid Polymer Electrolytes." Molecules 2023, 28(4), 1781. https://doi.org/10.3390/molecules28041781.

GHS Hazard Statements

• H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Properties:

Chemical and Physical Properties

Property Name	Property Value
Molecular Weight	116.16 g/mol
XLogP3-AA	-0.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	116.083729621 g/mol
Monoisotopic Mass	116.083729621 g/mol
Topological Polar Surface Area	37.3Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	94.7
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes
Physical Description	Diacetone alcohol appears as a clear colorless liquid with a pleasant odor. Flash point below 141 °F. Less dense than Water. Vapors heavier than air.
Boiling Point	328 °F at 760 mmHg (USCG, 1999)
Melting Point	-45 °F (USCG, 1999)
Density	0.938 At 68 °F (USCG, 1999)
Solubility	Miscible With Water, Alcohol, Ether, Other Solvents
Vapor Pressure	3.62 mmHg (USCG, 1999)

Source: PubChem

Source Species:

Artocarpus altilis.

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