tert-butyl 3-oxobutanoate

• ChemBase ID: 109032
• Molecular Formular: C8H14O3
• Molecular Mass: 158.19496
• Monoisotopic Mass: 158.09429431
• SMILES: CC(=O)CC(=O)OC(C)(C)C
• Canonical SMILES: CC(=O)CC(=O)OC(C)(C)C
• InChI: InChI=1S/C8H14O3/c1-6(9)5-7(10)11-8(2,3)4/h5H2,1-4H3
• InChIKey: JKUYRAMKJLMYLO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 3-oxobutanoate
• IUPAC Traditional name: tert-butyl 3-oxobutanoate
• Synonyms: tert-BUTYL ACETOACETATE; ACTB; tert-Butyl acetoacetate; TBAA; tert-Butyl 3-oxobutanoate; Acetoacetic acid tert-butyl ester; 乙酰乙酸叔丁酯

Database IDs

• CAS Number: 1694-31-1
• EC Number: 216-904-5
• MDL Number: MFCD00008811
• Beilstein Number: 1680303
• PubChem SID: 24845032; 24846862; 24892099; 162094731; 24878235
• PubChem CID: 15538

CALCULATED PROPERTIES

• Acid pKa: 9.3923
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.4316397
• LogD (pH = 7.4): 1.4272999
• Log P: 1.198362
• Molar Refractivity: 41.1136 cm^3
• Polarizability: 16.33082 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: APHA: ≤100 liquid; clear
• Melting Point: -38°C
• Boiling Point: 71-72 °C/11 mmHg(lit.); 71-72°C/11mm
• Flash Point: 150.8 °F; 66 °C; 76°C(169°F)
• Density: 0.954 g/mL at 25 °C(lit.); 0.961
• Refractive Index: 1.4200; n20/D 1.419; n20/D 1.419(lit.)

Safety Information

• German water hazard class: 1
• TSCA Listed: 是
• GHS Hazard statements: H227
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (GC); ≥98.0% (GC); ≥98.0% (w/w) (GC); 95+%; 97%; 98%; 98+%
• Grade: Lonza quality; produced by Wacker; purum; reagent grade
• Impurities: ≤0.1% water; ≤0.5% acid (as acetic acid); ≤2.0% tert-butanol
• Linear Formula: CH3COCH2COOC(CH3)3

DETAILS

MP Biomedicals - 05209591

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 537594

Packaging
1, 4 L in poly bottle
100, 500 mL in poly bottle

Sigma Aldrich - B88608

Packaging
100 mL in glass bottle

Sigma Aldrich - 10911

Other Notes
prices for bulk quantities on request

Sigma Aldrich - 688770

Packaging
1 kg in glass bottle

REFERENCES

• Alternative to Ethyl acetoacetate, A12544, allowing decarboxylative cleavage of the ester group by acid catalyzed thermolysis, as in a general synthesis of ɑ?-unsaturated ketones: Acta Chem. Scand., 17, 2216 (1963). Application in the synthesis of acyloins: Arkiv. Chem., 17, 457 (1961); levulinic acids and δ-keto nitriles: Acta Chem. Scand., 16, 1191, 1324 (1962). Alkylation, NBS bromination and decarboxylative cleavage provide a sequence for the regiospecific synthesis of ɑ-bromo ketones: Synth. Commun., 25, 1045 (1995).
• The dimetallated species reacts selectively with electrophiles at the 4-position: J. Am. Chem. Soc., 96, 1082 (1974); J. Org. Chem., 43, 788 (1978).