ChemicalBook > CAS DataBase List > 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione

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
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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
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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.

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N-Bromosuccinimide Price

TRC
Product number
N565525
Product name
4-Nitrothalidomide
Packaging
5mg
Price
$65
Updated
2021/12/16
Biosynth Carbosynth
Product number
FD165191
Product name
2-(2,6Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
Packaging
25mg
Price
$125
Updated
2021/12/16
AK Scientific
Product number
J52997
Product name
2-(2,6-Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
Packaging
250mg
Price
$248
Updated
2021/12/16
Biosynth Carbosynth
Product number
FD165191
Product name
2-(2,6Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
Packaging
100mg
Price
$310
Updated
2021/12/16
Biosynth Carbosynth
Product number
FD165191
Product name
2-(2,6Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
Packaging
250mg
Price
$450
Updated
2021/12/16
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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

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View Lastest Price from 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione manufacturers

ShenZhen H&D Pharmaceutical Technology Co., LTD
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
ShenZhen H&D Pharmaceutical Technology Co., LTD
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
Career Henan Chemical Co
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

19171-18-7, 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dioneRelated Search:

Pomalidomide Impurity 4 3-AMINOPHTHALIC ACID (R)-Pomalidomide 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione Pomalidomide Impurity 10 3,4-Diamino-4-oxobutyric acid DL-Glutamine (S)-Pomalidomide 2-(2,6-dioxopiperidin-3-yl)-4-(hydroxyamino)isoindoline-1,3-dione 3-Nitrophthalic acid Pomalidomide Impurity 2 Pomalidomide Impurity 6 Thalidomide 4-Hydroxy ThalidoMide Pomalidomide Pomalidomide Impurity 3 3-AMINOPHTHALIC ACID HYDROCHLORIDE 4-Aminophthalic acid

  • 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
  • 4-Nitrothalidomide
  • Pomalidomide Intermediates
  • Pomalidomide Impurity E
  • 4-nitro-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
  • 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindole-1,3-dione
  • Thalidomide 4-Nitro Impurity
  • 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-4-nitro-
  • (R)-2-(2,6-Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
  • 2-(2,6-dioxopiperidin-3-yl)-4-nitro-1H-isoindole-1,3(2H)-dione
  • 2-(2,6-dioxopiperidin-3-yl)-4-nitro-1H-isoindole-1,3(2H)-dio...
  • 2-(2,6-Dioxo-3-piperidyl)-4-nitroisoindoline-1,3-dione
  • Pomadomide impurity 9
  • 19171-18-7