tert-Butyl 4-oxopentanoate

Name: tert-Butyl 4-oxopentanoate
Brand: ChemScene
Availability: InStock
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CAS No. 2854-10-6
Cat. No. CS-0513936
Molecule weight172.22
Purity≥97%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 2854-10-6

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General Information

CAS No. 2854-10-6
Cat. No. CS-0513936
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₆O₃
Molecular Weight 172.22
Synonym(s) levulinic acid t-butyl ester
SMILES CC(CCC(OC(C)(C)C)=O)=O

Description

tert-Butyl 4-oxopentanoate features a ketone-functionalized aliphatic chain flanked by a robust tert-butyl ester group, enabling straightforward deprotection and integration into complex molecular architectures. This stable, bench-ready reagent facilitates efficient access to β-keto ester intermediates through controlled hydrolysis or reduction pathways.

Application

tert-Butyl 4-oxopentanoate serves as a versatile synthon in synthetic organic chemistry, enabling efficient access to γ-keto ester derivatives and functionalized heterocycles. Its α,β-unsaturated ketone moiety facilitates Michael additions and aldol-type condensations, while the tert-butyl ester group offers excellent bench stability and ease of subsequent deprotection under mild acidic conditions. The molecule functions reliably in multistep sequences requiring orthogonal functionality and is widely employed in the construction of bioactive scaffolds and complex natural product intermediates.

Synthesis

Route1
- In-stock
  
  123-76-2
- 75-65-0
- ~47%
- In-stock
  
  2854-10-6
References
- Chen, Fei; Song, Ke-Sheng; Wu, Yun-Dong; Yang, Dan Journal of the American Chemical Society, 2008 , vol. 130, # 2 p. 743 - 755
Route2
- 1025064-07-6
- 75-09-2
- ~82%
- In-stock
  
  2854-10-6
References
- Lin, Kuo-Wei; Tsai, Chi-Hui; Hsieh, L-Lin; Yan, Tu-Hsin Organic Letters, 2008 , vol. 10, # 10 p. 1927 - 1930
Route3
- In-stock
  
  98946-18-0
- In-stock
  
  123-76-2
- ~83%
- In-stock
  
  2854-10-6
References
- Armstrong, Alan; Brackenridge, Ian; Jackson, Richard F.W.; Kirk, Joanna M. Tetrahedron Letters, 1988 , vol. 29, # 20 p. 2483 - 2486

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 43.37
LogP 1.6973
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Ketone

Building Blocks Skeleton Fatty chain compounds

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tert-Butyl 4-oxopentanoate

CAS No. 2854-10-6

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