N-Methoxy-N-methylcyclobutanecarboxamide

Name: N-Methoxy-N-methylcyclobutanecarboxamide
Brand: ChemScene
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CAS No. 640768-72-5
Cat. No. CS-0036219
Molecule weight143.18
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+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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N-Methoxy-N-methylcyclobutanecarboxamide|CS-0036219

Structure of 640768-72-5

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General Information

CAS No. 640768-72-5
Cat. No. CS-0036219
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₁₃NO₂
Molecular Weight 143.18
Synonym(s) N-Methoxy-N-methyl-cyclobutanecarboxamide
SMILES CN(C(=O)C1CCC1)OC

Description

N-Methoxy-N-methylcyclobutanecarboxamide features a strained cyclobutane ring fused to a carbamoyl group, delivering enhanced reactivity in amide bond formation. The N-methoxy and N-methyl substituents synergize to stabilize the transition state during nucleophilic acyl substitution. This compound serves as a robust acyl transfer agent under mild conditions, enabling efficient coupling reactions in complex molecule synthesis.

Application

N-Methoxy-N-methylcyclobutanecarboxamide serves as a stable, bench-ready amide surrogate that facilitates nucleophilic acyl substitution reactions under mild conditions. Its cyclic structure imparts conformational rigidity and enhanced stability compared to linear analogs, while the N-OMe/N-Me combination enables efficient activation for coupling with amines, alcohols, and thiols. Functions effectively in amide bond formation and heterocycle synthesis, offering predictable reactivity and straightforward purification.

Synthesis

Route1
- 1117-97-1
- 5006-22-4
- ~87%
- In-stock
  
  640768-72-5
References
- Brachet, Etienne; Hamze, Abdallah; Peyrat, Jean-Francois; Brion, Jean-Daniel; Alami, Mouad Organic Letters, 2010 , vol. 12, # 18 p. 4042 - 4045
Route2
- In-stock
  
  765-85-5
- In-stock
  
  6638-79-5
- ~73%
- In-stock
  
  640768-72-5
References
- Muir, Calum W.; Kennedy, Alan R.; Redmond, Joanna M.; Watson, Allan J. B. Organic and Biomolecular Chemistry, 2013 , vol. 11, # 20 p. 3337 - 3340
Route3
- In-stock
  
  3721-95-7
- In-stock
  
  6638-79-5
- ~%
- In-stock
  
  640768-72-5
References
- Gilligan, Paul J.; Folmer, Beverly K.; Hartz, Richard A.; Koch, Stephanie; Nanda, Kausik K.; Andreuski, Stephen; Fitzgerald, Lawrence; Miller, Keith; Marshall, William J. Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 18 p. 4093 - 4102

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
Precautionary Statements : P261-P280-P304+P340

Quality Control

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Computational Chemistry Data

TPSA 29.54
LogP 0.8063
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Fatty ring compounds Cyclobutane compounds

Key Words

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N-Methoxy-N-methylcyclobutanecarboxamide

CAS No. 640768-72-5

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