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CAS Number 211108-50-8

Chemistry Building Blocks, Fluorinated Building Blocks, Materials, Monomers

Product Code B2211-500mg
Price £90 ex. VAT

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

Multiple functional groups

For facile synthesis

Fluorinated building block

Fluorinated piperidone building block

For drug discovery, medicinal chemistry, and biochemistry research

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High purity 211108-50-8

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

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

Product Details

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

MSDS Documentation

1-(tert-Butoxycarbonyl)-3-fluoro-4-piperidone1-(tert-Butoxycarbonyl)-3-fluoro-4-piperidone MSDS Sheet

Literature and Reviews

  1. Photochromic fentanyl derivatives for controlled μ-opioid receptor activation, R. Lahmy et al., Chem. Eur. J., 28, e202201515(2022); DOI: 10.1002/chem.202201515.
  2. Rapid and efficient microwave-assisted Friedländer quinoline synthesis, H. Bailey et al., ChemistryOpen, 9, 1113–1122(2020); DOI: 10.1002/open.202000247.
  3. 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.
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