tert-Butyl N-(2-hydroxyethyl)-N-methylcarbamate

Name: tert-Butyl N-(2-hydroxyethyl)-N-methylcarbamate
Brand: ChemScene
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CAS No. 57561-39-4
Cat. No. CS-D1212
Purity≥98%
MDL No.MFCD03425857

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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tert-Butyl N-(2-hydroxyethyl)-N-methylcarbamate|CS-D1212

Structure of 57561-39-4

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General Information

CAS No. 57561-39-4
Cat. No. CS-D1212
Purity ≥98%
MDL No. MFCD03425857
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₁₇NO₃
Molecular Weight 175.23
Synonym(s) Carbamic acid, (2-hydroxyethyl)methyl-, 1,1-dimethylethyl ester (9CI); (2-Hydroxyethyl)(methyl)carbamic acid tert-butyl ester; 1,1-Dimethylethyl (2-hydroxyethyl)methylcarbamate; tert-butyl (2-hydroxyethyl)methylcarbamate
SMILES OCCN(C(OC(C)(C)C)=O)C

Description

tert-Butyl N-(2-hydroxyethyl)-N-methylcarbamate features a hydroxyl-bearing ethyl linker flanking a tertiary butyl-protected carbamate, enabling selective deprotection under mild acidic conditions. This scaffold delivers stable, moisture-tolerant handling while integrating readily into peptide-coupling and bioconjugation workflows.

Application

tert-Butyl N-(2-hydroxyethyl)-N-methylcarbamate serves as a robust, bench-stable protecting group for primary amines, enabling selective derivatization in complex molecule synthesis. Its hydroxymethyl side chain facilitates downstream functionalization, while the tert-butyl carbamate moiety offers orthogonal stability under acidic and basic conditions. The compound functions effectively in amine protection strategies, particularly in peptide coupling and heterocycle construction, with straightforward deprotection via mild acid treatment.

Synthesis

Route1
- In-stock
  
  109-83-1
- In-stock
  
  24424-99-5
- ~97%
- In-stock
  
  57561-39-4
References
- Methylgene, Inc. Patent: US2007/4675 A1, 2007 ; Location in patent: Page/Page column 92-93 ; US 20070004675 A1
Route2
- In-stock
  
  109-83-1
- 41840-28-2
- ~80%
- In-stock
  
  57561-39-4
References
- Takeda Chemical Industries, Ltd Patent: US4962113 A1, 1990 ;
Route3
- In-stock
  
  109-83-1
- ~85%
- In-stock
  
  57561-39-4
References
- Zeneca Limited; Zeneca Pharma S. A. Patent: US6362336 B1, 2002 ; Location in patent: Example 54 ; US 6362336 B1

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 49.77
LogP 0.8456
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boc

Building Blocks Functional Group Amine

Building Blocks Functional Group Alcohol

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tert-Butyl N-(2-hydroxyethyl)-N-methylcarbamate

CAS No. 57561-39-4

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