1-(tert-Butoxycarbonyl)-3-fluoro-4-piperidone

CAS Number 211108-50-8

Chemistry Building Blocks, Fluorinated Building Blocks, Materials, Monomers

1-(tert-Butoxycarbonyl)-3-fluoro-4-piperidone MSDS

1-(tert-Butoxycarbonyl)-3-fluoro-4-piperidone CAS 211108-50-8

A fluorinated piperidone building block

As a molecular scaffold for drug discovery and bioimaging

Specifications | MSDS | Literature and Reviews

1-(tert-Butoxycarbonyl)-3-fluoro-4-piperidone (CAS number 211108-50-8), also known as 1-Boc-3-fluoro-4-piperidone, is a Boc (tert-butoxycarbonyl) protected piperidone bearing a fluorine substituent on 3-position. 1-(tert-Butoxycarbonyl)-3-fluoro-4-piperidone is the core of fentanyl, an opioid drug used as an analgesic. Fentanyl binds to opioid receptors leading to the inhibitory effects. To synthesize fentanyl derivatives, 1-(tert-butoxycarbonyl)-3-fluoro-4-piperidone reacts with aniline via reductive amination followed by nucleophilic substitution of propionyl chloride. Boc group is then removed with trifluoroacetic acid (TFA) and phenylethyl group is attached to form fentanyl.

Fentanyl chemical structure — Chemical structure of fentanyl, an analgesic drug.

Photochromic functional groups (such as azobenzene) can be easily attached to 1-(tert-butoxycarbonyl)-3-fluoro-4-piperidone for optically controlled μ-opioid receptor activation. The trans- and cis- formations of azo result significantly different receptor affinities that are photoswitchable. 1-(tert-Butoxycarbonyl)-3-fluoro-4-piperidone functionalized with chromophores can also be applied for bioimaging to study the binding affinity of the molecules.

Multiple functional groups

For facile synthesis

Fluorinated piperidone building block

For drug discovery, medicinal chemistry, and biochemistry research

Worldwide shipping

Quick and reliable shipping

High purity

>97% High purity

General Information

CAS Number	211108-50-8
Chemical Formula	C₁₀H₁₆FNO₃
Full Name	1-(tert-Butoxycarbonyl)-3-fluoro-4-piperidone
Molecular Weight	217.24 g/mol
Synonyms	1-Boc-3-fluoro-4-piperidone, tert-Butyl 3-fluoro-4-oxo-1-piperidinecarboxylate, 3-Fluoro-4-oxo-1-piperidinecarboxylic acid tert-butyl ester, 1-Boc-3-fluoro-4-oxopiperidine
Classification / Family	Fluorinated building block, Heterocyclic building block, Drug discovery, Bioimaging

Chemical Structure

Product Details

Purity	97%
Melting Point	T_m = 74.0 – 78.0 °C
Appearance	White to off-white powder

MSDS Documentation

1-(tert-Butoxycarbonyl)-3-fluoro-4-piperidone MSDS Sheet

Literature and Reviews

Photochromic fentanyl derivatives for controlled μ-opioid receptor activation, R. Lahmy et al., Chem. Eur. J., 28, e202201515(2022); DOI: 10.1002/chem.202201515.
Rapid and efficient microwave-assisted Friedländer quinoline synthesis, H. Bailey et al., ChemistryOpen, 9, 1113–1122(2020); DOI: 10.1002/open.202000247.
Evaluation of the alicyclic Gauche effect in 2-Fluorocyclohexanone analoges: a combined NMR and DFT study, D. Silva et al., Eur. J. Org. Chem., 884–890(2020); DOI: 10.1002/ejoc.201901815.

Fast & fluorinated – development and validation of a rapid benchtop NMR approach and other routine screening methods for the detection and quantification of synthesized fluorofentanyl derivatives, N. Gilbert et al., Forensic Chem., 23, 100321(2021); DOI: 10.1016/j.forc.2021.100321.