2-((tert-Butoxycarbonyl)amino)ethyl 4-methylbenzenesulfonate

Name: 2-((tert-Butoxycarbonyl)amino)ethyl 4-methylbenzenesulfonate
Brand: ChemScene
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CAS No. 158690-56-3
Cat. No. CS-0148612
Purity≥97%
MDL No.MFCD07776965

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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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2-((tert-Butoxycarbonyl)amino)ethyl 4-methylbenzenesulfonate|CS-0148612

Structure of 158690-56-3

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General Information

CAS No. 158690-56-3
Cat. No. CS-0148612
Purity ≥97%
MDL No. MFCD07776965
Storage -20°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₁NO₅S
Molecular Weight 315.38
Synonym(s) None
SMILES O=C(OC(C)(C)C)NCCOS(=O)(=O)C1=CC=C(C=C1)C

Description

This sulfonate ester features a tert-butoxycarbonyl-protected amine tethered to a 4-methylbenzenesulfonate leaving group. It enables selective amidation reactions under mild conditions, leveraging the stability of the Boc moiety and the reactivity of the aryl sulfonate. Ideal for peptide synthesis and bioconjugation workflows requiring orthogonal functionalization.

Application

2-((tert-Butoxycarbonyl)amino)ethyl 4-methylbenzenesulfonate serves as a versatile, bench-stable sulfonate ester for the introduction of protected amine functionalities in synthetic sequences. It facilitates efficient nucleophilic substitution reactions with diverse amines, enabling rapid access to N-Boc aminoalkyl derivatives under mild conditions. Its excellent functional group tolerance and straightforward purification profile make it ideal for building blocks in peptide synthesis and medicinal chemistry campaigns.

Synthesis

Route1
- In-stock
  
  26690-80-2
- 98-59-9
- ~94%
- In-stock
  
  158690-56-3
References
- McGouran, Joanna F.; Kramer, Holger B.; MacKeen, Mukram M.; Di Gleria, Katalin; Altun, Mikael; Kessler, Benedikt M. Organic and Biomolecular Chemistry, 2012 , vol. 10, # 17 p. 3379 - 3383
Route2
- In-stock
  
  24424-99-5
- ~%
- In-stock
  
  158690-56-3
References
- Journal of Labelled Compounds and Radiopharmaceuticals, , vol. 45, # 2 p. 115 - 137

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-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 81.7
LogP 2.22502
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Sulfonate

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-((tert-Butoxycarbonyl)amino)ethyl 4-methylbenzenesulfonate

CAS No. 158690-56-3

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