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

A14117 2,4-Pentanedione, 99%

Codice CAS
123-54-6
Sinonimi
Acetylacetone
acac

Dimensioni Prezzo ($) Quantità Disponibilità
100ml 27,50
500ml 40,02
2500ml 145,23
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2,4-Pentanedione, 99%

MDL
MFCD00008787
EINECS
204-634-0

Proprietà chimiche

Formula
C5H8O2
Peso formula
100.12
Punto di fusione
-23°
Punto di ebollizione
140-141°
Punto di infiammabilità
34°(93°F)
Densità
0.973
Indice di rifrazione
1.4520
Solubilità
It is readily miscible with water.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H311-H331-H302-H226

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

Dichiarazioni precauzionali: 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.

Altri riferimenti

Merck
14,81
Beilstein
741937
Classe di rischio
3
Gruppo di imballaggio
III
Codice tariffe armonizzato
2914.19
TSCA
Yes
RTECS
SA1925000

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