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537594

Sigma-Aldrich

tert-Butyl acetoacetate

reagent grade, 98%

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Synonym(s):
TBAA
Linear Formula:
CH3COCH2COOC(CH3)3
CAS Number:
Molecular Weight:
158.19
Beilstein/REAXYS Number:
1680303
MDL number:
PubChem Substance ID:

grade

reagent grade

Quality Level

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.)

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

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This Item
B88209364789236608
tert-Butyl acetoacetate reagent grade, 98%

537594

tert-Butyl acetoacetate

tert-Butyl acetate ≥99%

B88209

tert-Butyl acetate

Tri-tert-butyl borate 98%

236608

Tri-tert-butyl borate

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

mp

-38 °C (lit.)

mp

-

mp

21 °C (lit.)

mp

18-19 °C (lit.)

refractive index

n20/D 1.419 (lit.)

refractive index

n20/D 1.386 (lit.)

refractive index

n20/D 1.456 (lit.)

refractive index

n20/D 1.389 (lit.)

density

0.954 g/mL at 25 °C (lit.)

density

0.866 g/mL at 20 °C (lit.)

density

1.221 g/mL at 25 °C (lit.)

density

0.811 g/mL at 25 °C (lit.)

bp

71-72 °C/11 mmHg (lit.)

bp

97-98 °C (lit.)

bp

65 °C/11 mmHg (lit.)

bp

101 °C/74 mmHg (lit.)

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.

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

Storage Class

10 - Combustible liquids

wgk_germany

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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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)
Enzymatic Synergism in the Synthesis of ?-Keto Esters.
Wisniewska C, et al.
European Journal of Organic Chemistry, 24, 5432-5437 (2015)
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

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