pentane-2,4-dione

• ChemBase ID: 77902
• Molecular Formular: C5H8O2
• Molecular Mass: 100.11582
• Monoisotopic Mass: 100.0524295
• SMILES: O=C(CC(=O)C)C
• Canonical SMILES: CC(=O)CC(=O)C
• InChI: InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3
• InChIKey: YRKCREAYFQTBPV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pentane-2,4-dione
• IUPAC Traditional name: acetylacetone
• Synonyms: Hacac; Acetylacetone; Pentane-2,4-dione; AcAc; Acetylacetone; 2,4-Pentanedione; ACETYLACETONE; 2,4-PENTANEDIONE; 2,4-Pentanedione; 2,4-戊二酮; 乙酰丙酮; 2,4-戊烷二酮

Database IDs

• CAS Number: 123-54-6
• EC Number: 204-634-0
• MDL Number: MFCD00008787
• Beilstein Number: 741937
• Merck Index: 1481
• PubChem SID: 24898873; 24846889; 24845101; 162042745; 24845859
• PubChem CID: 31261
• CHEBI ID: 14750
• CHEMBL: 191625
• Chemspider ID: 29001
• KEGG ID: C15499
• Unique Ingredient Identifier: 46R950BP4J
• Wikipedia Title: Acetylacetone

CALCULATED PROPERTIES

• Acid pKa: 8.505447
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.32770538
• LogD (pH = 7.4): 0.295359
• Log P: 0.3281338
• Molar Refractivity: 26.09 cm^3
• Polarizability: 10.108824 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 16 g/100 mL in water; Water}
• Melting Point: -23 °C(lit.); -23°C; -23.3 °C; -23°C
• Boiling Point: 139 °C at 1013 hPa; 140°C; 140.4 °C(lit.); 140-141°C; 140-141°C
• Flash Point: 100 °F; 100.4 °F; 34°C (93.2°F); 34°C(93°F); 38 °C; 38°C; 40.5 °C (open cup)
• Auto Ignition Point: 340°C (644°F); 350 °C; 662 °F
• Density: .975 g/cm^3 at 20 °C; 0.973; 0.975; 0.975 g/mL; 0.975 g/mL at 25 °C(lit.)
• Refractive Index: 1.4520; n20/D 1.452; n20/D 1.452(lit.)
• Vapor Pressure: 6 mmHg ( 20 °C); 8.5 hPa at 20 °C
• Vapor Density: 3.5 (vs air)

Safety Information

• Storage Condition: Room Temperature (15-30°C), Protect from light
• Storage Warning: Flammable/Toxic/Harmful
• RTECS: SA1925000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2310; UN2310
• German water hazard class: 1
• Hazard Class: 3; 6.1
• Packing Group: 3; III
• Australian Hazchem: 2Y
• Risk Statements: 10-20/21/22; 10-22; R:10-22-36; R10, R22
• Safety Statements: 21-23-24/25; S:21-23-24/25; S2, S21, S23, S24/25
• EU Classification: FT1
• EU Hazard Identification Number: 6.1A
• Emergency Response Guidebook(ERG) Number: 131
• TSCA Listed: 是
• EU Index: 606-029-00-0
• GHS Pictograms: GHS02; GHS06; GHS07
• GHS Signal Word: Danger
• NFPA704:
  

  2

  2

  0
• Explode Limits: 11.4 %; 2.4–11.6%
• GHS Hazard statements: H226-H302; H226-H302-H311-H331
• GHS Precautionary statements: P210-P241-P280-P303+P361+P353-P403+P235-P501A; P261-P280-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2310 3/PG 3

Pharmacology Properties

• Gene Information: human ... ACHE(43), BCHE(590), CES1(1066)

Product Information

• Purity: ~99%; ≥98.0% (GC); ≥99%; ≥99.3%; ≥99.5% (GC); ≥99.6% (GC); 98%; 99%
• Grade: analytical standard; JIS special grade; produced by Wacker; puriss. p.a.; purum; ReagentPlus®
• Impurities: ≤0.01% ethyl acetate
• Cation Traces: Al: ≤0.5 mg/kg; Ba: ≤0.1 mg/kg; Bi: ≤0.1 mg/kg; Ca: ≤0.5 mg/kg; Cd: ≤0.05 mg/kg; Co: ≤0.02 mg/kg; Cr: ≤0.02 mg/kg; Cu: ≤0.02 mg/kg; Fe: ≤0.1 mg/kg; K: ≤0.5 mg/kg; Li: ≤0.1 mg/kg; Mg: ≤0.1 mg/kg; Mn: ≤0.02 mg/kg; Mo: ≤0.1 mg/kg; Na: ≤0.5 mg/kg; Ni: ≤0.02 mg/kg; Pb: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: ≤0.1 mg/kg
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: CH3COCH2COCH3

DETAILS

MP Biomedicals - 02151812

Purity: ~99%
Used to form derivatives of amino acids for peptide synthesis. Also used in colorimetric triglyceride assays.
1 ml = approx. 0.97 g
This product may darken during storage.

Sigma Aldrich - 10916

Other Notes
prices for bulk quantities on request
Packaging
1 kg in poly bottle

Sigma Aldrich - P7754

Application
Transition-metal chelating agent
Packaging
1 L in glass bottle
100, 500 mL in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 00900

Other Notes
Indicator for the complexometric titration of Fe(III)1; For the modification of guanidino groups in proteins (e.g. Arg)2; and amino groups in proteins3,4

Sigma Aldrich - 516937

Legal Information
Manufactured by Wacker Chemie AG

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).