2,4-Piperadinedione
- Product Name
- 2,4-Piperadinedione
- CAS No.
- 50607-30-2
- Chemical Name
- 2,4-Piperadinedione
- Synonyms
- Piperidine-2,4-dione;PIPERIDIN-2,4-DIONE;2,4-Piperidinedione;2,4-PIPERADINEDIONE;2,4-Dioxopiperidine;2,4-Diketopiperidine;2,4-PiperadinedioneE;2,4-Piperidinedione>Piperidine-2,4-dione 97%;2,4-Piperidinedione, 98%
- CBNumber
- CB3511804
- Molecular Formula
- C5H7NO2
- Formula Weight
- 113.11
- MOL File
- 50607-30-2.mol
2,4-Piperadinedione Property
- Melting point:
- 98.0 to 102.0 °C
- Boiling point:
- 362.1±35.0 °C(Predicted)
- Density
- 1.184±0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- form
- powder to crystal
- pka
- 12.00±0.70(Predicted)
- color
- White to Orange to Green
- InChI
- InChI=1S/C5H7NO2/c7-4-1-2-6-5(8)3-4/h1-3H2,(H,6,8)
- InChIKey
- RDNZDMDLRIQQAX-UHFFFAOYSA-N
- SMILES
- N1CCC(=O)CC1=O
Safety
- Hazard Codes
- Xn
- Risk Statements
- 22-36/37/38-43
- Safety Statements
- 26-36/37
- RIDADR
- UN 3335
- WGK Germany
- 3
- HS Code
- 2933790090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H317May cause an allergic skin reaction
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 759368
- Product name
- 2,4-Piperidinedione
- Purity
- 97%
- Packaging
- 250mg
- Price
- $64.5
- Updated
- 2025/07/31
- Product number
- P2296
- Product name
- 2,4-Piperidinedione
- Purity
- >98.0%(GC)(T)
- Packaging
- 200mg
- Price
- $19
- Updated
- 2025/07/31
- Product number
- P2296
- Product name
- 2,4-Piperidinedione
- Purity
- >98.0%(GC)(T)
- Packaging
- 1g
- Price
- $60
- Updated
- 2025/07/31
- Product number
- P480020
- Product name
- 2,4-Piperidinedione
- Packaging
- 2.5g
- Price
- $120
- Updated
- 2021/12/16
- Product number
- P480020
- Product name
- 2,4-Piperidinedione
- Packaging
- 5g
- Price
- $165
- Updated
- 2021/12/16
2,4-Piperadinedione Chemical Properties,Usage,Production
Description
2,4-Piperidinedione is an important piperidine ring-containing intermediate, and its 2,4-piperidinedione, as a characteristic fragment, is widely used as an intermediate in the synthesis of ibrutinib and paliperidone drugs.
Chemical Properties
White to light yellow solid
Uses
2,4-Piperidinedione is a reactant in the synthesis of 1,4-dihydropyridines as TGFβ/Smad inhibitors.
Preparation
The synthesis of 2,4-Piperidinedione involved dissolving 400 mg (2.34 mmol, 1.00 eq.) of Methyl 2,4-dioxo-piperidine-3-carboxylate in a mixture of acetonitrile (20 mL) and water (0.2 mL). The solution was then heated to approximately 86° C. and maintained at this temperature for around 4 hours. After completion of the reaction, the solvent was removed under vacuum, leaving behind a residue of 2,4-Piperidinedione. This residue was further purified using silica gel column chromatography with a mobile phase consisting of dichloromethane and methanol in a ratio of 100:1. The target product, 2,4-Piperidinedione, was obtained as a white solid, with a yield of 27%, corresponding to 70 mg.
Synthesis
845267-78-9
50607-30-2
The general procedure for the synthesis of 2,4-piperidinediones from tert-butyl 2,4-dipiperidone-1-carboxylate was as follows: at 0 °C and under nitrogen protection, Boc-β-alanine (25 g, 132 mmol), Meldrum acid (20.9 g, 145 mmol), and 4-dimethylaminopyridine (DMAP, 24.2 g, 198 mmol) were dissolved in 700 mL of anhydrous dichloromethane (DCM). To this solution was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 30.4 g, 158 mmol). The reaction mixture was slowly warmed to room temperature and stirred overnight. After completion of the reaction, the reaction mixture was washed with 5% KHSO4 aqueous solution (0.5 L x 4). The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product [tert-butyl [3-(2,2-dimethyl-4,6-dioxo-[1,3]dioxol-5-yl)-3-oxo-propyl]-carbamate. The crude product was dissolved in 600 mL of ethyl acetate and refluxed for 4 hours. It was concentrated under reduced pressure to a volume of about 150 mL and subsequently crystallized at 4°C overnight. The solid was collected by filtration and washed with cold ethyl acetate to afford 18.4 g (65% yield) of 2,4-piperidinedione.1H NMR (400 MHz, DMSO-D6) δppm: 1.44 (s, 9H), 2.44 (m, 2H), 3.71 (m, 2H), 4.95 (s, 1H), 11.2 (bs, 1H). The resulting product was converted quantitatively to piperidine-2,4-dione by dissolving in dichloromethane and treating with trifluoroacetic acid for 3 h at room temperature.
References
[1] Patent: WO2008/104475, 2008, A1. Location in patent: Page/Page column 22
[2] Patent: WO2012/35078, 2012, A1. Location in patent: Page/Page column 144
[3] Patent: US2014/45872, 2014, A1. Location in patent: Paragraph 0911
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 3, p. 487 - 501
[5] Angewandte Chemie - International Edition, 2014, vol. 53, # 14, p. 3594 - 3598
2,4-Piperadinedione Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 2,4-Piperadinedione manufacturers
- Product
- Piperidine-2,4-dione 50607-30-2
- Price
- US $200.00-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%, 99.5% Sublimated
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2023-12-30
- Product
- 2,4-Piperadinedione 50607-30-2
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- Customized
- Release date
- 2018-08-09
- Product
- 2,4-PiperadinedioneE 50607-30-2
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 97%
- Supply Ability
- 200KG
- Release date
- 2018-08-15