(S)-2-Azido-3,3-dimethylbutanoic acid

Name: (S)-2-Azido-3,3-dimethylbutanoic acid
Brand: ChemScene
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CAS No. 111525-71-4
Cat. No. CS-0611185
Purity≥97%
MDL No.None

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(S)-2-Azido-3,3-dimethylbutanoic acid|CS-0611185

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General Information

CAS No. 111525-71-4
Cat. No. CS-0611185
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₁₁N₃O₂
Molecular Weight 157.17
Synonym(s) (S)-alpha-Azido-3,3-dimethylbutyric acid
SMILES CC(C)(C)[C@H](N=[N+]=[N-])C(O)=O

Description

(S)-2-Azido-3,3-dimethylbutanoic acid features a stereodefined chiral center and a terminal azide group flanked by two methyl-substituted carbon atoms. This configuration imparts enhanced stability and facilitates efficient bioorthogonal conjugation in synthetic biology applications. The steric shielding from the geminal dimethyl groups reduces side reactivity while maintaining solubility in common organic solvents.

Application

(S)-2-Azido-3,3-dimethylbutanoic acid serves as a versatile chiral building block for the synthesis of non-natural amino acids and peptidomimetics. Its tertiary α-carbon enhances steric definition, while the azide group enables efficient copper-catalyzed azide-alkyne cycloaddition (CuAAC) for bioconjugation and heterocycle formation. The compound exhibits excellent bench stability, facilitates straightforward purification, and tolerates a range of functional groups, making it well-suited for modular synthetic strategies in medicinal chemistry and process development.

Synthesis

Route1
- 104266-91-3
- ~%
- In-stock
  
  111525-71-4
References
- Evans, David A.; Britton, Thomas C. Journal of the American Chemical Society, 1987 , vol. 109, # 22 p. 6881 - 6883

Safety Information

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

TPSA 86.06
LogP 1.796
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Fatty chain compounds

Building Blocks Functional Group Azide

Building Blocks Functional Group Carboxylic Acid

Chemical Biology Conjugation Chemistry/Click Chemistry Azides

Chemical Biology Pharmaceutical Development and Drug Discovery Research Conjugation Chemistry/Click Chemistry Azides

Key Words

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(S)-2-Azido-3,3-dimethylbutanoic acid

CAS No. 111525-71-4

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