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537594

Sigma-Aldrich

tert-Butyl acetoacetate

reagent grade, 98%

Synonym(s):

TBAA

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About This Item

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

grade

reagent grade

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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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 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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

537594-VAR:
537594-500ML:
537594-4L:
537594-100ML:
537594-20L:
537594-18L:
537594-2L:
537594-1L:
537594-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Transacetoacetylation with tert-butyl acetoacetate: synthetic applications.
Witzeman JS and Nottingham WD.
The Journal of Organic Chemistry, 56(5), 1713-1718 (1991)
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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