butane-2,3-dione

• ChemBase ID: 89667
• Molecular Formular: C4H6O2
• Molecular Mass: 86.08924
• Monoisotopic Mass: 86.03677943
• SMILES: O=C(C)C(=O)C
• Canonical SMILES: CC(=O)C(=O)C
• InChI: InChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3
• InChIKey: QSJXEFYPDANLFS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: butane-2,3-dione
• IUPAC Traditional name: diacetyl
• Synonyms: Biacetyl; Dimethyl diketone; 2,3-Diketobutane; Diacetyl; Butane-2,3-dione; Diacetyl; Dimethylglyoxal; biacetyl; 2,3-Butanedione; 2,3-Butanedione; 双乙酰; 联乙酰; 2,3-丁二酮; 2,3-丁烷二酮

Database IDs

• CAS Number: 431-03-8
• EC Number: 207-069-8
• MDL Number: MFCD00008756
• Beilstein Number: 605398
• Merck Index: 142966
• PubChem SID: 24846980; 24858987; 24892076; 162076530
• PubChem CID: 650
• CHEBI ID: 16583
• CHEMBL: 365809
• Chemspider ID: 630
• KEGG ID: C00741
• Unique Ingredient Identifier: K324J5K4HM
• Wikipedia Title: Diacetyl

CALCULATED PROPERTIES

• Acid pKa: 15.977073
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.39549947
• LogD (pH = 7.4): 0.39549947
• Log P: 0.39549947
• Molar Refractivity: 21.5408 cm^3
• Polarizability: 8.28327 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Soluble in 4 parts in water
• Apperance: Yellowish green liquid
• Melting Point: -2 to -4 °C; -3°C; -4 to -2°C
• Boiling Point: 87-88°C; 88 °C(lit.); 88°C; 88 °C
• Flash Point: 10°C(50°F); 44.6 °F; 7 °C; 7-10°C
• Auto Ignition Point: 345 °C
• Density: 0.981; 0.981 g/mL(lit.); 0.983; 0.985 g/mL at 20 °C; 0.990 g/mL at 15 °C
• Refractive Index: 1.3950; n20/D 1.394; n20/D 1.394(lit.)
• Vapor Pressure: 52.2 mmHg ( 20 °C)
• Vapor Density: 3 (vs air)
• Transition Temperature: solidification point -3-1 °C

Safety Information

• Storage Warning: Highly Flammable/Toxic/Harmful/Irritant/Stench/Moisture Sensitive/Air Sensitive/Keep Cold/Store under Argon
• RTECS: EK2625000
• European Hazard Symbols: Flammable (F); X; Harmful (Xn)
• UN Number: 2346; UN2346
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-20/22-36/38; 11-20/22-37/38-41; R10 R22 R36 R37 R38
• Safety Statements: 16-26-36/37; 26-39; S9 S16 S33
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• Main Hazard: Harmful, flammable
• GHS Hazard statements: H225-H302-H315-H318-H331-H335; H225-H302-H332-H315-H319
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P403+P235-P501A; P210-P261-P280-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, Heavyweight Gloves, multi-purpose combination respirator cartridge (US), Safety Clothing, type ABEK (EN14387) respirator filter; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2346 3/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

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

Product Information

• Purity: ≥99.0% (GC); 97%; 98%; 99%
• Grade: analytical standard; puriss.
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: CH3COCOCH3

DETAILS

Sigma Aldrich - B85307

Packaging
5, 100, 500 mL in glass bottle
Application
Inactivates aminopeptidase-N.1 Cyclocondensation with amines has been used to form triazine2 and pteridine ring systems.3 Also used as a precursor to α-diones.4

Sigma Aldrich - 31530

Other Notes
Reagent for the specific modification of arginine residues in proteins1,2,3,4

REFERENCES

• Sensitizer for the photochemical epoxidation of alkenes: J. Am. Chem. Soc., 98, 4193 (1976).
• Like 1,2-Cyclohexanedione, A14401, has been used by Ley's group in combination with trimethyl orthoformate and camphorsulfonic acid for the protection of trans-1,2-diols as cyclic diacetals. The method is particularly applicable to the carbohydrate field: Synlett, 793 (1996); J. Chem. Soc., Perkin 1, 2023 (1997). See also 9,10-Phenanthrenequinone, A11762.