2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
- Product Name
- 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
- CAS No.
- 19171-18-7
- Chemical Name
- 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
- Synonyms
- 4-Nitrothalidomide;Pomadomide impurity 9;Pomalidomide Impurity E;Pomalidomide Intermediates;Thalidomide 4-Nitro Impurity;2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindole-1,3-dione;2-(2,6-Dioxo-3-piperidyl)-4-nitroisoindoline-1,3-dione;2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione;4-nitro-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione;(R)-2-(2,6-Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
- CBNumber
- CB42623812
- Molecular Formula
- C13H9N3O6
- Formula Weight
- 303.23
- MOL File
- 19171-18-7.mol
2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione Property
- Melting point:
- >200°C (dec.)
- Boiling point:
- 603.4±50.0 °C(Predicted)
- Density
- 1.651±0.06 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Acetonitrile (Slightly, Heated, Sonicated), DMSO (Slightly)
- pka
- 10.55±0.40(Predicted)
- form
- Solid
- color
- Pale Yellow to Pale Beige
- InChI
- InChI=1S/C13H9N3O6/c17-9-5-4-8(11(18)14-9)15-12(19)6-2-1-3-7(16(21)22)10(6)13(15)20/h1-3,8H,4-5H2,(H,14,17,18)
- InChIKey
- KVRCAGKHAZRSQX-UHFFFAOYSA-N
- SMILES
- C1(=O)C2=C(C([N+]([O-])=O)=CC=C2)C(=O)N1C1CCC(=O)NC1=O
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
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
- N565525
- Product name
- 4-Nitrothalidomide
- Packaging
- 5mg
- Price
- $65
- Updated
- 2021/12/16
- Product number
- FD165191
- Product name
- 2-(2,6Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
- Packaging
- 25mg
- Price
- $125
- Updated
- 2021/12/16
- Product number
- J52997
- Product name
- 2-(2,6-Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
- Packaging
- 250mg
- Price
- $248
- Updated
- 2021/12/16
- Product number
- FD165191
- Product name
- 2-(2,6Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
- Packaging
- 100mg
- Price
- $310
- Updated
- 2021/12/16
- Product number
- FD165191
- Product name
- 2-(2,6Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
- Packaging
- 250mg
- Price
- $450
- Updated
- 2021/12/16
2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione Chemical Properties,Usage,Production
Uses
4-Nitrothalidomide is a compound involved in the preparation of Pomalidomide (P688200), a thalidomide derivative and potent inhibitor of TNF-α production.
Synthesis
641-70-3
24666-56-6
19171-18-7
A solution of glacial acetic acid (75 mL) and 3-aminopiperidine-2,6-dione hydrochloride (8.5 g) was added to a round bottom flask. Anhydrous sodium acetate (4.5 g) was added to the solution in batches at 25 °C to 30 °C, followed by 3-nitrophthalic anhydride (10 g) at the same temperature. The reaction mixture was stirred at 118 °C for 18 hours. After completion of the reaction, the reaction material was cooled to 60 °C and the solvent was removed by distillation under vacuum to obtain a residue. Water (100 mL) was added to the residue and the mixture was stirred at 25 °C to 30 °C for 1 hour, followed by filtration. The wet filter cake was slurried with water (100 mL x 2), filtered and dried in an air pan drier to less than 0.5% water to give 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione (14 g). Yield: 89.7%, purity: 98%.
References
[1] Patent: US2017/260157, 2017, A1. Location in patent: Page/Page column 5
[2] Patent: CN104926786, 2017, B. Location in patent: Paragraph 0044; 0045
[3] Synthetic Communications, 2016, vol. 46, # 16, p. 1343 - 1348
[4] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 11, p. 1625 - 1630
[5] Patent: CN104402863, 2016, B. Location in patent: Paragraph 0035
2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione Preparation Products And Raw materials
Raw materials
Preparation Products
2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione Suppliers
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View Lastest Price from 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione manufacturers
- Product
- Pomalidomide Impurity 9 19171-18-7
- Price
- US $0.00-0.00/mg
- Min. Order
- 10mg
- Purity
- 98%
- Supply Ability
- 500mg
- Release date
- 2024-06-27
- Product
- Pomalidomide Impurity 10 19171-18-7
- Price
- US $0.00-0.00/mg
- Min. Order
- 10mg
- Purity
- 98%
- Supply Ability
- 500mg
- Release date
- 2024-06-27
- Product
- 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione 19171-18-7
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 95-99%
- Supply Ability
- 1ton
- Release date
- 2020-01-02