Methyl 1-bromocyclobutane-1-carboxylate

Name: Methyl 1-bromocyclobutane-1-carboxylate
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CAS No. 51175-79-2
Cat. No. CS-0037271
Purity≥98%
MDL No.None

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Methyl 1-bromocyclobutane-1-carboxylate|CS-0037271

Structure of 51175-79-2

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General Information

CAS No. 51175-79-2
Cat. No. CS-0037271
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₉BrO₂
Molecular Weight 193.04
Synonym(s) Methyl 1-bromocyclobutanecarboxylate
SMILES COC(=O)C1(CCC1)Br

Description

Methyl 1-bromocyclobutane-1-carboxylate is a strained cyclobutane derivative featuring a bromide at the ring junction and an ester group for downstream functionalization. This configuration enables direct incorporation into cross-coupling reactions or nucleophilic substitution processes under mild conditions. The molecule exhibits enhanced reactivity due to ring strain and bears a handle for further derivatization in synthetic sequences.

Application

Methyl 1-bromocyclobutane-1-carboxylate serves as a versatile cyclobutane-containing building block for transition-metal-catalyzed couplings and nucleophilic substitution reactions. The bromide functionality enables reliable functionalization, while the ester group offers compatibility with standard deprotonation and conjugate addition protocols. Its bench-stable crystalline form facilitates handling and purification, making it suitable for iterative synthesis of complex cyclic architectures in medicinal chemistry and materials science applications.

Synthesis

Route1
- 67-56-1
- In-stock
  
  3721-95-7
- ~90%
- In-stock
  
  51175-79-2
References
- Estieu, Karine; Ollivier, Jean; Salauen, Jacques Tetrahedron Letters, 1996 , vol. 37, # 5 p. 623 - 624
Route2
- 67-56-1
- ~%
- In-stock
  
  51175-79-2
References
- Perkin; Sinclair Journal of the Chemical Society, 1892 , vol. 61, p. 44

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 26.3
LogP 1.477
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Fatty ring compounds Cyclobutane compounds

Key Words

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Methyl 1-bromocyclobutane-1-carboxylate

CAS No. 51175-79-2

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