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A14117 2,4-Pentanedione, 99%

CAS Number
123-54-6
Synonyms
Acetylacetone
acac

Stock No. Size Price ($) Quantity Availability
A14117-AE 100ml 28.30
A14117-AP 500ml 41.30
A14117-0F 2500ml 153.00
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2,4-Pentanedione, 99%

MDL
MFCD00008787
EINECS
204-634-0

Chemical Properties

Formula
C5H8O2
Formula Weight
100.12
Melting point
-23°
Boiling Point
140-141°
Flash Point
34°(93°F)
Density
0.973
Refractive Index
1.4520
Storage & Sensitivity
Ambient temperatures.
Solubility
It is readily miscible with water.

Applications

2,4-Pentanedione is used as a precursor to acetylacetonate, a common bidentate and a raw material for the synthesis of heterocyclic compounds. It is used in pharmaceuticals, organic intermediates for solvents, analytical reagents, tungsten and molybdenum in aluminum extraction agent.

Notes

Incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides.

Literature References

A simple procedure for the synthesis of methyl ketones involves alkylation at the 3-position with an alkyl halide using K2CO3 in EtOH, with in situ acetyl cleavage: Org. Synth. Coll., 5, 767 (1973). Knoevenagel condensation with aldehydes in THF in the presence of K2CO3 also occurs with acetyl cleavage, providing a simple route to alkenyl ketones: Chem. Lett., 1325 (1978). With K2CO3 and TBAB, selective one-pot monoalkylation or dialkylation with different alkyl groups can be achieved: Synthesis, 688 (1989). 3-Arylation with aryl bromides takes place in the presence of Cu(I) or Cu(II) salts in DMF: Chem. Lett., 597 (1982); Org. Synth. Coll., 6, 36 (1988).

Strong bases, e.g. NaNH2, form the dianion which reacts with electrophiles, e.g. alkyl halides, esters, acyl halides, Michael acceptors, etc., at the less-stabilized terminal carbon: J. Org. Chem., 26, 1716 (1961); Tetrahedron Lett., 357 (1970); J. Org. Chem., 39, 2289 (1974); Org. Synth. Coll., 5, 848 (1973). For arylation at the 1-position, see Diphenyl­iodonium chloride, A15149. For reviews of dimetallation, see: Org. React., 17, 155 (1969); Synthesis, 509 (1977).

/n

Freeman, F. Mechanisms of Reactions of Sulfur Hydride Hydroxide: Tautomerism, Condensations, and C-Sulfenylation and O-Sulfenylation of 2,4-Pentanedione. J. Phys. Chem. A 2015, 119 (14), 3500-3517.

Freeman, F. Mechanisms of Reactions of Sulfur Hydride Hydroxide: Tautomerism, Condensations, and C-Sulfenylation and O-Sulfenylation of 2, 4-Pentanedione. J. Phys. Chem. A 2015, 199 (14), 3500-3517.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H302-H311-H331

Flammable liquid and vapour. Harmful if swallowed. Toxic in contact with skin. Toxic if inhaled.

Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P261-P264b-P270-P271-P280-P301+P312-P303+P361+P353-P304+P340-P311-P312-P330-P363-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician. Rinse mouth. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,81
Beilstein
741937
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2914.19
TSCA
Yes
RTECS
SA1925000

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