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537594 Sigma-Aldrich

tert-Butyl acetoacetate

reagent grade, 98%

Synonym: TBAA

  • CAS Number 1694-31-1

  • Linear Formula CH3COCH2COOC(CH3)3

  • Molecular Weight 158.19

  •  Beilstein/REAXYS Number 1680303

  •  MDL number MFCD00008811

  •  PubChem Substance ID 24878235

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Properties

Related Categories ACS and Reagent Grade Solvents, Amber Glass Bottles, Building Blocks, C8 to C9, Carbonyl Compounds,
Quality Level   100
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

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. 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

Packaging

1, 4 L in poly bottle

100, 500 mL in poly bottle

Safety & Documentation

Safety Information

WGK Germany 
WGK 1
Flash Point(F) 
150.8 °F - closed cup
Flash Point(C) 
66 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Meet Synthia - Retrosynthesis Sofware
Protocols & Articles

Articles

Pressure-Temperature Calculator for Solvents

*Calculations provide estimated results based on Antoine's Coefficients and their associated temperature range values. Antoine's Coefficients were obtained from the National Institute of Standards an...

Peer-Reviewed Papers
15

References

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