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Merck

537594

tert-Butyl acetoacetate

reagent grade, 95%

Synonym(s):

TBAA

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About This Item

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

Product Name

tert-Butyl acetoacetate, reagent grade, 95%

InChI

1S/C8H14O3/c1-6(9)5-7(10)11-8(2,3)4/h5H2,1-4H3

SMILES string

CC(=O)CC(=O)OC(C)(C)C

InChI key

JKUYRAMKJLMYLO-UHFFFAOYSA-N

grade

reagent grade

assay

95%

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

Quality Level

100

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Application

tert-Butyl acetoacetate may be used in the synthesis of:
  • various acetoacetic acid derivatives
  • acetoacetates
  • acetoacetamides
  • 1-(diethylamino)-2-acetoacetoxypropane
  • (S)-tert-butyl 3-hydroxybutyrate
  • benzothiazole β-keto ester derivatives
  • 3,4-disubstituted pyrroles

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. It is widely employed as an acetoacetylating reagent.

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

150.8 °F - closed cup

flash_point_c

66 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ9143
MKCK4314
MKCB0832V
MKBD4606V
MKBL4718V

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Transesterification.
Otera J.
Chemical Reviews, 93(4), 1449-1470 (1993)
Deborah A Smithen et al.
Organic & biomolecular chemistry, 11(1), 62-68 (2012-10-17)
Prodigiosenes, possessing a 4-methoxypyrrolyldipyrrin skeleton, are known for their anti-cancer activity. Structural modification of the C-ring resulted in a series of prodigiosenes that displayed promising activity against leukemia cell lines during in vitro analysis against the NCI 60 cancer cell
Enzymatic Synergism in the Synthesis of ?-Keto Esters.
Wisniewska C, et al.
European Journal of Organic Chemistry, 24, 5432-5437 (2015)
Highly enantioselective Mannich reactions of imines with tert-butyl acetoacetate catalyzed by squaramide organocatalyst.
He HX and Du DM.
Tetrahedron Asymmetry, 25(8), 637-643 (2014)
Synthesis of (S)-Tert-Butyl 3-Hydroxybutyrate by Asymmetric Reduction of Tert-Butyl Acetoacetate with Saccharomyces cerevisiae B5.
Ou ZM, et al.
Advanced Materials Research, 704 (2013)
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