acetyl acetate

• ChemBase ID: 104081
• Molecular Formular: C4H6O3
• Molecular Mass: 102.08864
• Monoisotopic Mass: 102.03169405
• SMILES: CC(=O)OC(=O)C
• Canonical SMILES: CC(=O)OC(=O)C
• InChI: InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
• InChIKey: WFDIJRYMOXRFFG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: acetyl acetate
• IUPAC Systematic name: ethanoic anhydride
• IUPAC Traditional name: acetic anhydride
• Synonyms: Acetic anhydride, ACS; Ethanoyl ethanoate; Acetic acid anhydride; Acetyl acetate; Acetyl oxide; Cap A (acetic anhydride 10% in THF); Cap A (acetic anhydride 12% in acetonitrile); Acetic anhydride solution; Cap A (acetic anhydride 10% in THF/pyridine 8 : 1); Cap A (acetic anhydride 10% in THF/lutidine 8 : 1); Acetic Acid, Anhydride; Acetic Oxide; Acetyl Anhydride; Anhydride Acetique; ACETIC ANHYDRIDE; Acetic anhydride; 醋酐, ACS; 醋酸酐; 乙酸酐 溶液; Cap A（10% 乙酸酐溶于 THF）; Cap A（12% 乙酸酐溶于乙腈）; 乙酸酐

Database IDs

• CAS Number: 108-24-7
• EC Number: 203-564-8
• MDL Number: MFCD00008705
• Beilstein Number: 385737
• Merck Index: 1456
• PubChem SID: 24846953; 162092426; 24878429; 24854587; 24889455; 24891084; 24860032; 24859248
• PubChem CID: 7918
• CHEBI ID: 36610
• Chemspider ID: 7630
• Unique Ingredient Identifier: 2E48G1QI9Q
• Wikipedia Title: Acetic_anhydride

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.31251943
• LogD (pH = 7.4): -0.31251943
• Log P: -0.31251943
• Molar Refractivity: 22.082 cm^3
• Polarizability: 9.04463 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 2.6 g/100 mL, see text in water
• Apperance: clear liquid; Liquid
• Melting Point: -73 °C; -73 °C(lit.); -73.1°C; -73°C
• Boiling Point: 138 - 140.5 °C at 1013 hPa; 138-140 °C(lit.); 138-140°C; 139.8°C
• Flash Point: -.4 °F; 1.4 °F; 12 °C; 120.2 °F; -17 °C; -18 °C; 49 °C; 49°C(120°F); 53.6 °F; 58°C
• Auto Ignition Point: 316 °C; 330 °C; 629 °F
• Density: 0.819 g/mL at 20 °C; 0.906 g/mL at 20 °C; 0.911 g/mL at 20 °C; 0.917 g/mL at 20 °C; 1.08 g/mL(lit.); 1.081 g/mL at 20 °C; 1.082; 1.082 g cm^-3, liquid; 1.082 g/cm^3 at 20 °C
• Refractive Index: 1.3900; 1.3901; n20/D 1.390; n20/D 1.390(lit.)
• Vapor Pressure: 10 mmHg ( 36 °C); 4 hPa at 20 °C; 4 mmHg ( 20 °C)
• Vapor Density: 3.5 (air = 1); 3.5 (vs air)

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• Storage Warning: Moisture Sensitive
• RTECS: AK1925000
• European Hazard Symbols: Corrosive (C); Flammable (F); X; Irritant (Xi); Harmful (Xn)
• UN Number: 1715; 2924; UN1715
• German water hazard class: 1; 2; 3
• Hazard Class: 3; 8
• Packing Group: 2; II
• Australian Hazchem: 2W
• Risk Statements: 10-20/22-34; 11-19-20/21/22-37/38-41; 11-19-37/38-41; 11-20/21/22-37/38-41; R:10-20/22-34; R10, R20/22, R34
• Safety Statements: 16-26-36/37/39; 16-26-39; 26-36/37/39-45; S:26-45-36/37/39; S1/2, S26, S36/37/39, S45
• EU Classification: CF1
• EU Hazard Identification Number: 8A
• Emergency Response Guidebook(ERG) Number: 137
• TSCA Listed: 是
• EU Index: 607-008-00-9
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• NFPA704:
  

  2

  2

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• Explode Limits: 10.3 %; 2.7–10.3%
• GHS Hazard statements: H225-H302-H315-H318-H331-H335; H225-H315-H318-H335; H226-H302-H314-H332; H314-H226-H302-H332
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P280-P305 + P351 + P338; P210-P261-P280-P305 + P351 + P338-P311; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1715 8/PG 2; UN 2924 3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides.

Product Information

• Purity: ≥93.0%; ≥98%; ≥98.0%; ≥98.0% (GC); ≥99%; ≥99% (GC); ≥99.0%; ≥99.0% (GC); ≥99.0% (NT); ≥99.5% (GC); 97+%; 99.5%; 99+%
• Grade: ACS reagent; for DNA synthesis; for GC derivatization; JIS special grade; Lonza quality; puriss. p.a.; purum; reagent grade; ReagentPlus®; SAJ first grade
• Packaging: pkg of 10 × 2 mL
• Suitability: passes test for reaction against H2SO4
• Evaporation Residue: ≤0.003%
• Impurities: ≤0.003% non-volatile matter; ≤0.005% water; ≤0.01% KMnO4 red. matter (as O); ≤0.01% water; ≤0.5% acetic acid; MnO4- reducers, passes test
• Cation Traces: Al: ≤0.5 mg/kg; B: ≤0.02 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: ≤0.05 mg/kg; Cr: ≤0.1 mg/kg; Cu: ≤0.02 mg/kg; Fe: ≤0.1 mg/kg; Fe: ≤0.5 mg/kg; Fe: ≤5 ppm; heavy metals: ≤2 ppm; 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; Ni: ≤0.1 mg/kg; Pb: ≤0.1 mg/kg; Sn: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: ≤0.1 mg/kg; Zn: ≤0.2 mg/kg
• Antion Traces: chloride (Cl-): ≤2 mg/kg; chloride (Cl-): ≤5 ppm; phosphate (PO43-): ≤0.001%; phosphate (PO43-): ≤10 mg/kg; sulfate (SO42-): ≤5 mg/kg; sulfate (SO42-): ≤5 ppm
• Derivatization reagent for: Acetylations; Acylations; Silylations
• Linear Formula: (CH3CO)2O

DETAILS

MP Biomedicals - 02154680

1 ml = approx. 1.08 g

Sigma Aldrich - 691275

Analysis Note
KMnO4 test ≤40 mL (0.1% KMnO4 per 20 mL)
Packaging
25 kg in comp drum

Sigma Aldrich - 95193

Application
Reagent used in the phosphite triester method of oligonucleotide synthesis for the capping of the remaining free 5′-hydroxyl groups by acetylation. Reagent is suitable for use on ABI, Beckman synthesizers.
Preparation Note
filtered with a 0.1 μm filter

Sigma Aldrich - 45830

Other Notes
For the unspecific acetylation of functional groups (NH2, OH and SH) in proteins1; For the specific blocking of side chain amino groups2; Review3

Sigma Aldrich - 30908

Application
Reagent used in the phosphite triester method of oligonucleotide synthesis for the capping of the remaining free 5’-hydroxyl groups by acetylation. Reagent is suitable for use on Biosearch 8000, Expedite, Cyclone synthesizers.
Preparation Note
filtered with a 0.1 μm filter

Sigma Aldrich - 49929

Application
Reagent used in the phosphite triester method of oligonucleotide synthesis for the capping of the remaining free 5’-hydroxyl groups by acetylation. Reagent is suitable for use on ABI synthesizers.
Preparation Note
filtered with a 0.1 μm filter

Sigma Aldrich - 45840

Other Notes
Sales restrictions may apply

Sigma Aldrich - 11659

Application
Reagent used in the phosphite triester method of oligonucleotide synthesis for the capping of the remaining free 5’-hydroxyl groups by acetylation. Reagent is suitable for use on Milligen 7500 synthesizers.
Preparation Note
filtered with a 0.1 μm filter

Sigma Aldrich - 539996

Packaging
1, 4 kg in glass bottle
18 kg in poly drum
25 g in glass bottle

Sigma Aldrich - 320102

Packaging
1 L in glass bottle
1 kg in PVC coated
100, 500 mL in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - A6404

包装
1, 2.5 L in glass bottle
200, 500 mL in glass bottle

Sigma Aldrich - 242845

Packaging
1, 6×1, 3 kg in glass bottle
5, 100 g in glass bottle

Sigma Aldrich - 33085

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.

REFERENCES

• Rates of acetylation of alcohols and phenols can be greatly increased by hypernucleophilic catalysis with DMAP (4-(Dimethylamino)pyridine, A13016). See also 2-Hydroxypyridine, A14522 and Tri-n-butylphosphine, A12649. The use of certain metal triflates as catalysts is also effective; see, e.g. Scandium(III) trifluoromethanesulfonate hydrate, 40566, and Ytterbium(III) trifluoromethanesulfonate hydrate, 40314. CoCl₂ catalysis in acetonitrile has been reported to promote selective acetylation of primary alcohols in the presence of secondary and tertiary: J. Org. Chem., 57, 2001 (1992), and formation of 1,1-diacetoxy-derivatives from aromatic aldehydes, but with aliphatic aldehydes, 1,2-diones are formed: J. Org. Chem., 56, 3283 (1991); 58, 5578 (1993).
• Can be used to activate Dimethyl sulfoxide, A13280, for mild, selective oxidation of alcohols to aldehydes or ketones (Albright-Goldman oxidation) at room temperature without added base (cf Swern: Oxalyl chloride, A18012): J. Am. Chem. Soc., 43, 2480 (1965); J. Org. Chem., 53, 2144 (1988).