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123-54-6 - 2,4-Pentanedione, 99% - Acetylacetone - acac - A14117 - Alfa Aesar

A14117 2,4-Pentanedione, 99%

CAS-Nummer
123-54-6
Synonyme
Acetylacetone
acac

Größe Preis ($) Menge Verfügbarkeit
100ml 27,50
500ml 40,02
2500ml 145,23
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

2,4-Pentanedione, 99%

MDL
MFCD00008787
EINECS
204-634-0

Chemische Eigenschaften

Formel
C5H8O2
Molmasse
100.12
Schmelzpunkt
-23°
Siedepunkt
140-141°
Flammpunkt
34°(93°F)
Dichte
0.973
Brechungsindex
1.4520
Löslichkeit
It is readily miscible with water.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H311-H331-H302-H226

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

Sicherheitshinweise: P210-P261-P280-P240-P303+P361+P353-P361-P304+P340-P311-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Merck
14,81
Beilstein
741937
Gefahrenklasse
3
Verpackungsgruppe
III
Harmonized Tariff Code
2914.19
TSCA
Yes
RTECS
SA1925000

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