1-(tert-Butoxycarbonyl)-3-fluoroazetidine-3-carboxylic acid

Name: 1-(tert-Butoxycarbonyl)-3-fluoroazetidine-3-carboxylic acid
Brand: ChemScene
Availability: InStock
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CAS No. 1126650-67-6
Cat. No. CS-0003939
Purity≥95%
MDL No.MFCD15071784

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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+
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1-(tert-Butoxycarbonyl)-3-fluoroazetidine-3-carboxylic acid|CS-0003939

Structure of 1126650-67-6

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General Information

CAS No. 1126650-67-6
Cat. No. CS-0003939
Purity ≥95%
MDL No. MFCD15071784
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₄FNO₄
Molecular Weight 219.21
Synonym(s) 3-Fluoro-1,3-azetidinedicarboxylicacid tert-butyl ester
SMILES O=C(C1(F)CN(C(OC(C)(C)C)=O)C1)O

Description

1-(tert-Butoxycarbonyl)-3-fluoroazetidine-3-carboxylic acid features a strained azetidine ring bearing a fluorine atom at the 3-position and a tert-butoxycarbonyl protecting group. This configuration imparts enhanced metabolic stability and facilitates selective incorporation into peptide scaffolds. The compound serves as a key building block for fluorinated cyclic amino acids in medicinal chemistry and bioconjugation applications.

Application

1-(tert-Butoxycarbonyl)-3-fluoroazetidine-3-carboxylic acid serves as a stable, bench-ready building block for the synthesis of fluorinated azetidine-containing scaffolds. The tert-butyl carbamate group enables straightforward deprotection under mild acidic conditions, while the 3-fluoroazetidine core provides enhanced metabolic stability and conformational rigidity. It reacts efficiently in standard amide coupling protocols and functions as a key intermediate in the construction of bioactive heterocycles relevant to medicinal chemistry and process development.

Synthesis

Route1
- In-stock
  
  1126650-66-5
- ~48%
- In-stock
  
  1126650-67-6
References
- Van Hende, Eva; Verniest, Guido; Deroose, Frederik; Thuring, Jan-Willem; Macdonald, Gregor; De Kimpe, Norbert Journal of Organic Chemistry, 2009 , vol. 74, # 5 p. 2250 - 2253

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 66.84
LogP 1.03
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Fluoride

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aliphatic heterocycle compounds Azetidine compounds

Key Words

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1-(tert-Butoxycarbonyl)-3-fluoroazetidine-3-carboxylic acid

CAS No. 1126650-67-6

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