1-(tert-Butyl) 2-methyl (S)-aziridine-1,2-dicarboxylate

Name: 1-(tert-Butyl) 2-methyl (S)-aziridine-1,2-dicarboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 126496-79-5
Cat. No. CS-0052393
Purity≥95%
MDL No.MFCD10566310

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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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1-(tert-Butyl) 2-methyl (S)-aziridine-1,2-dicarboxylate|CS-0052393

Structure of 126496-79-5

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General Information

CAS No. 126496-79-5
Cat. No. CS-0052393
Purity ≥95%
MDL No. MFCD10566310
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₅NO₄
Molecular Weight 201.22
Synonym(s) (S)-N-tert-butoxycarbonyl aziridine-2-carboxylate methyl ester
SMILES O=C(N1[C@H](C(OC)=O)C1)OC(C)(C)C

Description

This chiral aziridine derivative features a (S)-configured ring flanked by a tert-butyl ester and a methyl ester, offering enhanced stability and stereochemical integrity. The sterically encumbered tert-butyl group minimizes unwanted side reactions, while the electron-deficient aziridine ring facilitates selective ring-opening under mild conditions. Ideal for asymmetric synthesis and catalyst design.

Application

A bench-stable, chiral building block that serves as a versatile precursor in asymmetric synthesis. The (S)-aziridine moiety enables stereoselective ring-opening reactions with nucleophiles, while the tert-butyl and methyl ester groups provide orthogonal reactivity and ease of purification. Functions effectively in the construction of nitrogen-containing heterocycles and bioactive scaffolds under standard conditions.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  75154-68-6
- ~89%
- In-stock
  
  126496-79-5
References
- Wu, Yan-Chao; Zhu, Jieping Organic Letters, 2009 , vol. 11, # 23 p. 5558 - 5561
Route2
- In-stock
  
  24424-99-5
- 75154-69-7
- ~73%
- In-stock
  
  126496-79-5
References
- Baldwin, Jack E.; Farthing, Christopher N.; Russell, Andrew T.; Schofield, Christopher J.; Spivey, Alan C. Tetrahedron Letters, 1996 , vol. 37, # 21 p. 3761 - 3764

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

Quality Control

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Computational Chemistry Data

TPSA 55.61
LogP 0.7787
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Oxane compounds

Key Words

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1-(tert-Butyl) 2-methyl (S)-aziridine-1,2-dicarboxylate

CAS No. 126496-79-5

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