Benzyl 3-methyleneazetidine-1-carboxylate

Name: Benzyl 3-methyleneazetidine-1-carboxylate
Brand: ChemScene
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CAS No. 934664-23-0
Cat. No. CS-0183114
Purity≥97%
MDL No.None

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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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Benzyl 3-methyleneazetidine-1-carboxylate|CS-0183114

Structure of 934664-23-0

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General Information

CAS No. 934664-23-0
Cat. No. CS-0183114
Purity ≥97%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₃NO₂
Molecular Weight 203.24
Synonym(s) benzyl 3-methylideneazetidine-1-carboxylate
SMILES C=C1CN(C1)C(=O)OCC2=CC=CC=C2

Description

Benzyl 3-methyleneazetidine-1-carboxylate is a reactive azetidine derivative featuring a strained four-membered ring with an exocyclic methylene group. This electrophilic moiety enables efficient ring-opening reactions and facilitates direct incorporation into complex molecular architectures under mild conditions. The benzyl ester handle enhances solubility and stability during handling, streamlining downstream transformations in synthetic sequences.

Application

Benzyl 3-methyleneazetidine-1-carboxylate serves as a versatile building block for the synthesis of nitrogen-containing heterocycles, enabling efficient access to azetidinyl motifs via cycloaddition and ring-opening reactions. The methylene group facilitates [2+2] cycloadditions and acts as a site for functionalization, while the benzyl ester provides stability and ease of purification. Its compatibility with diverse reaction conditions makes it valuable in medicinal chemistry and process development workflows.

Synthesis

Route1
- 1779-49-3
- In-stock
  
  105258-93-3
- ~75%
- In-stock
  
  934664-23-0
References
- EXELIXIS, INC. Patent: WO2008/124085 A2, 2008 ; Location in patent: Page/Page column 179-180 ; WO 2008/124085 A2
Route2
- In-stock
  
  105258-93-3
- ~74%
- In-stock
  
  934664-23-0
References
- EXELIXIS, INC. Patent: WO2007/44515 A1, 2007 ; Location in patent: Page/Page column 165-166 ; WO 2007/044515 A1

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 29.54
LogP 2.195
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Azetidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Benzyl 3-methyleneazetidine-1-carboxylate

CAS No. 934664-23-0

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