537594

tert-Butyl acetoacetate

reagent grade, 98%

• Synonym(s): TBAA
• Linear Formula: CH₃COCH₂COOC(CH₃)₃
• CAS Number: 1694-31-1
• Molecular Weight: 158.19
• Beilstein: 1680303
• MDL number: MFCD00008811
• UNSPSC Code: 12352100
• PubChem Substance ID: 24878235
• NACRES: NA.22

Properties

• grade: reagent grade
• Quality Level: 100
• Assay: 98%
• expl. lim.: 8 % (lit.)
• impurities: ≤0.20% water; water
• refractive index: n20/D 1.419 (lit.)
• bp: 71-72 °C/11 mmHg (lit.)
• mp: -38 °C (lit.)
• density: 0.954 g/mL at 25 °C (lit.)
• functional group: ester; ketone
• SMILES string: CC(=O)CC(=O)OC(C)(C)C
• InChI: 1S/C8H14O3/c1-6(9)5-7(10)11-8(2,3)4/h5H2,1-4H3
• InChI key: JKUYRAMKJLMYLO-UHFFFAOYSA-N

Description

General description

tert-Butyl acetoacetate (t-BAA) is a cheap and easy to store commercial reagent. Reaction demonstrated that the more hindered tert-butyl acetoacetate (t-BAA, la) is ca.15-20-fold more reactive than the more commonly used methyl or ethyl analogs.[1] It is widely employed as an acetoacetylating reagent.[2]

Application

tert-Butyl acetoacetate may be used in the synthesis of:

• various acetoacetic acid derivatives[1][3]
• acetoacetates[1]
• acetoacetamides[1]
• 1-(diethylamino)-2-acetoacetoxypropane[1]
• (S)-tert-butyl 3-hydroxybutyrate[4]
• benzothiazole β-keto ester derivatives[5]
• 3,4-disubstituted pyrroles[6]

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 1
• Flash Point(F): 150.8 °F - closed cup
• Flash Point(C): 66 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves