Product Name

  • Name

    3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione

  • EINECS 1592732-453-0
  • CAS No. 827026-45-9
  • Article Data39
  • CAS DataBase
  • Density 1.546 g/cm3
  • Solubility
  • Melting Point
  • Formula C13H11N3O5
  • Boiling Point 616.562 °C at 760 mmHg
  • Molecular Weight 289.247
  • Flash Point 326.685 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 827026-45-9 (3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione)
  • Hazard Symbols
  • Synonyms 3-(4-Nitro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione;3-(4-Nitro-1-oxoisoindolin-2-yl)piperidin-2,6-dione;
  • PSA 112.30000
  • LogP 1.14570

Synthetic route

rac-α-aminoglutarimide hydrochloride
24666-56-6

rac-α-aminoglutarimide hydrochloride

2-bromomethyl-3-nitro-benzoic acid methyl ester
98475-07-1

2-bromomethyl-3-nitro-benzoic acid methyl ester

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Stage #1: rac-α-aminoglutarimide hydrochloride With triethylamine In dimethyl sulfoxide for 0.166667h; Inert atmosphere;
Stage #2: 2-bromomethyl-3-nitro-benzoic acid methyl ester In dimethyl sulfoxide at 50 - 55℃; for 12.3333h; Inert atmosphere;		99.73%
With sodium carbonate at 100℃; for 0.75h; Reagent/catalyst; Temperature; Inert atmosphere;98.5%
With sodium carbonate In acetonitrile at 70℃; for 8h; Solvent; Reagent/catalyst; Temperature;98.8%
2-bromomethyl-3-nitro-benzoic acid methyl ester
98475-07-1

2-bromomethyl-3-nitro-benzoic acid methyl ester

(+/-)-α-aminoglutarimide
2353-44-8

(+/-)-α-aminoglutarimide

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 3h; Reflux;96%
Stage #1: 2-bromomethyl-3-nitro-benzoic acid methyl ester; (+/-)-α-aminoglutarimide With sodium carbonate In acetonitrile at 5℃; Inert atmosphere; Reflux; Large scale;
Stage #2: With hydrogenchloride In water at 20 - 62℃; for 4h; pH=< 6; Large scale;		79.5%
With triethylamine In N,N-dimethyl-formamide at 25 - 100℃; for 7h; Inert atmosphere;
With potassium hydrogencarbonate In acetonitrile Reflux;
With triethylamine In N,N-dimethyl-formamide at 75℃; for 20h;
3-(4-nitro-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione

3-(4-nitro-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
With 5-trimethylammonio-1,3-dioxo-1,3-dihydro-1λ5-benzo[d][1,2]-iodoxol-1-ol anion In water at 50 - 70℃;94.1%
With tert.-butylhydroperoxide; copper(ll) sulfate pentahydrate; oxygen In 1,4-dioxane at 70℃; for 3h; Temperature; Reagent/catalyst; Solvent;78%
methyl 2-(chloromethyl)-3-nitrobenzoate

methyl 2-(chloromethyl)-3-nitrobenzoate

rac-α-aminoglutarimide hydrochloride
24666-56-6

rac-α-aminoglutarimide hydrochloride

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
With triethylamine In acetonitrile at 80℃; for 10h;93.2%
2-methyl-3-nitro-benzoic acid methyl ester
59382-59-1

2-methyl-3-nitro-benzoic acid methyl ester

(+/-)-α-aminoglutarimide
2353-44-8

(+/-)-α-aminoglutarimide

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; zinc dibromide In 1,4-dioxane at 95℃; Temperature;90.7%
2-amino-3-tert-butoxypropionic acid
17083-25-9

2-amino-3-tert-butoxypropionic acid

2-bromomethyl-3-nitro-benzoic acid methyl ester
98475-07-1

2-bromomethyl-3-nitro-benzoic acid methyl ester

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Stage #1: 2-amino-3-tert-butoxypropionic acid; 2-bromomethyl-3-nitro-benzoic acid methyl ester With sodium hydrogencarbonate In acetonitrile at 5 - 20℃; Reflux;
Stage #2: With hydrogenchloride In water at 58 - 62℃; for 4.16667h; pH=< 6; Temperature; Time;		79.5%
4-carbamoyl-4-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)butyric acid
1198299-72-7

4-carbamoyl-4-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)butyric acid

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide at 0℃;78%
methyl 2-(chloromethyl)-3-nitrobenzoate

methyl 2-(chloromethyl)-3-nitrobenzoate

(+/-)-α-aminoglutarimide
2353-44-8

(+/-)-α-aminoglutarimide

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
With ammonium hydroxide In N,N-dimethyl-formamide for 2h; Reflux;75%
2-bromomethyl-3-nitro-benzoic acid methyl ester
98475-07-1

2-bromomethyl-3-nitro-benzoic acid methyl ester

(RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate

(RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 20 - 50℃; for 40.5h; Inert atmosphere;73%
3-aminopiperidine-2,6-dione hydrobromide
90802-45-2

3-aminopiperidine-2,6-dione hydrobromide

2-bromomethyl-3-nitro-benzoic acid methyl ester
98475-07-1

2-bromomethyl-3-nitro-benzoic acid methyl ester

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20 - 80℃; for 10h;65.2%
3-aminopiperidine-2,6-dione hydrochloric acid salt

3-aminopiperidine-2,6-dione hydrochloric acid salt

2-bromomethyl-3-nitro-benzoic acid methyl ester
98475-07-1

2-bromomethyl-3-nitro-benzoic acid methyl ester

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl acetamide at 85℃; for 4h;56%
2-methyl-3-nitro-benzoic acid methyl ester
59382-59-1

2-methyl-3-nitro-benzoic acid methyl ester

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NBS / CCl4 / Heating; Irradiation
2: Et3N / dimethylformamide / 80 °C
View Scheme
Multi-step reaction with 2 steps
1.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 93 h / Reflux
2.1: acetonitrile / 0.25 h / 20 °C
2.2: 7 h / 20 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / chlorobenzene / 6 h / 90 - 95 °C / Inert atmosphere
2: triethylamine / N,N-dimethyl-formamide / 7 h / 25 - 100 °C / Inert atmosphere
View Scheme
Cbz-L-Gln
2650-64-8

Cbz-L-Gln

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CDI / tetrahydrofuran / Heating
2: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
3: Et3N / dimethylformamide / 80 °C
View Scheme
Multi-step reaction with 2 steps
1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2.5 h / 25 - 70 °C
2.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 25 - 35 °C
2.2: 6 h / 25 - 35 °C
View Scheme
Multi-step reaction with 3 steps
1: dmap; 1,1'-carbonyldiimidazole / 1,4-dioxane / 15 h / 100 °C
2: hydrogen bromide; acetic acid / 1 h / 60 °C
3: triethylamine / acetonitrile / 10 h / 20 - 80 °C
View Scheme
3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2, aq. HCl / 10 percent Pd/C / ethyl acetate / 2585.74 - 3102.89 Torr
2: Et3N / dimethylformamide / 80 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogen bromide; acetic acid / 1 h / 60 °C
2: triethylamine / acetonitrile / 10 h / 20 - 80 °C
View Scheme
2-(4-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-pentanedioic acid diamide

2-(4-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-pentanedioic acid diamide

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
With formamide at 160 - 170℃; Product distribution / selectivity;
2-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)glutaric acid dimethyl ester
827026-43-7

2-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)glutaric acid dimethyl ester

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
With formamide at 160 - 170℃; Product distribution / selectivity;
With sodium amide In tetrahydrofuran; water at 20℃; Product distribution / selectivity;
N-benzyloxycarbonyl-L-isoglutamine
6398-06-7

N-benzyloxycarbonyl-L-isoglutamine

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dmap; 1,1'-carbonyldiimidazole / tetrahydrofuran / 20 h / Reflux
2.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 23 h / 760.05 Torr
3.1: acetonitrile / 0.25 h / 20 °C
3.2: 7 h / 20 °C / Reflux
View Scheme
N-(2,6-dioxopiperidin-3-yl)-2-phenylacetamide

N-(2,6-dioxopiperidin-3-yl)-2-phenylacetamide

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 23 h / 760.05 Torr
2.1: acetonitrile / 0.25 h / 20 °C
2.2: 7 h / 20 °C / Reflux
View Scheme
2-bromomethyl-3-nitro-benzoic acid methyl ester
98475-07-1

2-bromomethyl-3-nitro-benzoic acid methyl ester

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine
24666-55-5

3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Stage #1: 3-(benzyloxycarbonyl)-amino-2,6-dioxopiperidine With palladium 10% on activated carbon; hydrogen In methanol at 25 - 35℃; for 2h;
Stage #2: 2-bromomethyl-3-nitro-benzoic acid methyl ester With triethylamine In N,N-dimethyl-formamide at 25 - 35℃; for 6h;		77 g
(S)-methyl 5-amino-2-(tert-butoxycarbonylamino)-5-oxopentanoate
4976-88-9

(S)-methyl 5-amino-2-(tert-butoxycarbonylamino)-5-oxopentanoate

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,1'-carbonyldiimidazole; dmap / tetrahydrofuran / 48 h / Reflux
2: water; sodium chloride / 4 h / Reflux
3: N,N-dimethyl-formamide / 3 h / Reflux
View Scheme
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester
31140-42-8

(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water; sodium chloride / 4 h / Reflux
2: N,N-dimethyl-formamide / 3 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: trifluoroacetic acid / dichloromethane / 20 °C
2: potassium hydrogencarbonate / acetonitrile / Reflux
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / water; tert-butyl methyl ether / 0.33 h / 0 °C
2: ammonium hydroxide / N,N-dimethyl-formamide / 2 h / Reflux
View Scheme
Boc-Gln-OH
13726-85-7

Boc-Gln-OH

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dicyclohexyl-carbodiimide; dmap / acetonitrile / 20 °C
2: trifluoroacetic acid / dichloromethane / 20 °C
3: potassium hydrogencarbonate / acetonitrile / Reflux
View Scheme
2-methyl-3-nitrobenzic acid
1975-50-4

2-methyl-3-nitrobenzic acid

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride / dichloromethane / Reflux
1.2: Reflux
2.1: bromine / tetrachloromethane / 20 °C
3.1: potassium hydrogencarbonate / acetonitrile / Reflux
View Scheme
Multi-step reaction with 3 steps
1: bis(trichloromethyl) carbonate / N,N-dimethyl-formamide / 6 h / Reflux
2: N-Bromosuccinimide; dibenzoyl peroxide / 8 h / Reflux
3: triethylamine / acetonitrile / 3 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: acetone / 0.17 h / 25 - 30 °C
1.2: 1.5 h / 25 - 30 °C
2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile / 12 h / 55 - 60 °C
3.1: triethylamine / dimethyl sulfoxide / 0.17 h / Inert atmosphere
3.2: 12.33 h / 50 - 55 °C / Inert atmosphere
View Scheme
L-glutamic acid
56-86-0

L-glutamic acid

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: water / 2 h / 0 °C
2: urea / dimethyl sulfoxide / 2 h / 150 °C
3: hydrogenchloride / dimethyl sulfoxide
4: triethylamine / acetonitrile / 3 h / Reflux
View Scheme
N-benzyloxycarbonyl-L-glutamic acid
1155-62-0

N-benzyloxycarbonyl-L-glutamic acid

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: urea / dimethyl sulfoxide / 2 h / 150 °C
2: hydrogenchloride / dimethyl sulfoxide
3: triethylamine / acetonitrile / 3 h / Reflux
View Scheme
4-nitroisoindoline

4-nitroisoindoline

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper(l) iodide; potassium carbonate / tetrahydrofuran / 6 h / 60 °C
2: 5-trimethylammonio-1,3-dioxo-1,3-dihydro-1λ5-benzo[d][1,2]-iodoxol-1-ol anion / water / 50 - 70 °C
View Scheme
3-(4-nitro-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione

3-(4-nitro-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione

A

4-NT
19171-18-7

4-NT

B

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

C

3-(4-nitro-3-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione
1063995-54-9

3-(4-nitro-3-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
With potassium permanganate In water at 50 - 70℃;
...Expand
isoindoline
496-12-8

isoindoline

A

4-NT
19171-18-7

4-NT

B

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

C

3-(4-nitro-3-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione
1063995-54-9

3-(4-nitro-3-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: nitric acid; sulfuric acid / 8.5 h / 20 °C / Cooling with ice
2: copper(l) iodide; potassium carbonate / tetrahydrofuran / 6 h / 60 °C
3: potassium permanganate / water / 50 - 70 °C
View Scheme
...Expand
isoindoline
496-12-8

isoindoline

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: nitric acid; sulfuric acid / 8.5 h / 20 °C / Cooling with ice
2: copper(l) iodide; potassium carbonate / tetrahydrofuran / 6 h / 60 °C
3: 5-trimethylammonio-1,3-dioxo-1,3-dihydro-1λ5-benzo[d][1,2]-iodoxol-1-ol anion / water / 50 - 70 °C
View Scheme
3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Lenalidomide
879126-98-4, 879126-99-5, 191732-72-6

Lenalidomide

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In ethanol at 40℃; under 3000.3 Torr; Pressure; Temperature;98.2%
With sodium sulfide; ethanol at 20℃; for 1h;98%
With sodium tetrahydroborate; ammonium chloride In ethanol; water at 90℃; for 1h; Reagent/catalyst;98%
3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

4-nitro-1-thioxo-2-(2-oxo-6-thioxopiperidine-3-yl)phthalimidine
1195729-61-3

4-nitro-1-thioxo-2-(2-oxo-6-thioxopiperidine-3-yl)phthalimidine

Conditions
ConditionsYield
With Lawessons reagent In toluene for 26h; Inert atmosphere; Reflux;85.8%
With Lawessons reagent In 1,4-dioxane for 5h; Reflux;64%
3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

(RS)-3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione hydrochloride
1243329-97-6

(RS)-3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione hydrochloride

Conditions
ConditionsYield
Stage #1: 3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione With hydrogen; palladium 10% on activated carbon In methanol at 21 - 35℃; under 2400.24 Torr; for 18h;
Stage #2: With hydrogenchloride In water		83.5%
methanesulfonic acid
75-75-2

methanesulfonic acid

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

methanesulfonate salt of 3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)-piperidine-2,6-dione

methanesulfonate salt of 3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)-piperidine-2,6-dione

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In methanol under 4654.46 Torr;
With hydrogen; palladium 10% on activated carbon In methanol at 30℃; under 4654.46 Torr; for 3 - 4h;
3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Reaxys ID: 20308519

Reaxys ID: 20308519

methanesulfonic acid
75-75-2

methanesulfonic acid

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)piperidine-2,6-dione methylsufonate
1187443-54-4

3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)piperidine-2,6-dione methylsufonate

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In methanol at 30℃; under 4654.46 Torr;
With palladium 10% on activated carbon; hydrogen In water at 25 - 30℃; under 4654.46 Torr;
3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

(RS)-3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione hydrogen sulfate
1243330-05-3

(RS)-3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione hydrogen sulfate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen / palladium 10% on activated carbon / methanol / 42 h / 2362.74 Torr
2: sulfuric acid / water / 50 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogen / palladium 10% on activated carbon / methanol / 18 h / 21 - 35 °C / 2400.24 Torr
2: sodium hydrogencarbonate / water / 65 - 70 °C / pH 8
3: sulfuric acid / water / 50 °C
View Scheme
3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

(RS)-3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione sulfate

(RS)-3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione sulfate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen / palladium 10% on activated carbon / methanol / 42 h / 2362.74 Torr
2: sulfuric acid / acetic acid / 0.75 h / 70 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogen / palladium 10% on activated carbon / methanol / 18 h / 21 - 35 °C / 2400.24 Torr
2: sodium hydrogencarbonate / water / 65 - 70 °C / pH 8
3: sulfuric acid / acetic acid / 0.75 h / 70 °C
View Scheme
3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

(RS)-3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione sulfate/hydrogen sulfate

(RS)-3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione sulfate/hydrogen sulfate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen / palladium 10% on activated carbon / methanol / 42 h / 2362.74 Torr
2: sulfuric acid / water / 50 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogen / palladium 10% on activated carbon / methanol / 18 h / 21 - 35 °C / 2400.24 Torr
2: sodium hydrogencarbonate / water / 65 - 70 °C / pH 8
3: sulfuric acid / water / 50 °C
View Scheme
3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione
827026-45-9

3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

1,6′-dithiolenalidomide
1195729-60-2

1,6′-dithiolenalidomide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Lawessons reagent / toluene / 26 h / Inert atmosphere; Reflux
2: palladium 10% on activated carbon; hydrogen / methanol / 69 h / 20 °C
View Scheme

3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione Specification

The CAS register number of 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione is 827026-45-9. It also can be called as 2,6-Piperidinedione,3-(1,3-dihydro-4-nitro-1-oxo-2H-isoindol-2-yl)- and the systematic name about this chemical is 3-(4-nitro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione.

Physical properties about 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione are: (1)ACD/LogP: 0.23; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 15; (5)ACD/KOC (pH 7.4): 15; (6)#H bond acceptors: 8; (7)#H bond donors: 1; (8)#Freely Rotating Bonds: 2; (9)Polar Surface Area: 112.3Å2; (10)Index of Refraction: 1.657; (11)Molar Refractivity: 68.769 cm3; (12)Molar Volume: 187.058 cm3; (13)Polarizability: 27.262x10-24cm3; (14)Surface Tension: 73.899 dyne/cm; (15)Enthalpy of Vaporization: 91.447 kJ/mol; (16)Boiling Point: 616.562 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: [O-][N+](=O)c2cccc1C(=O)N(Cc12)C3C(=O)NC(=O)CC3
(2)InChI: InChI=1/C13H11N3O5/c17-11-5-4-10(12(18)14-11)15-6-8-7(13(15)19)2-1-3-9(8)16(20)21/h1-3,10H,4-6H2,(H,14,17,18)
(3)InChIKey: JKPJLYIGKKDZDT-UHFFFAOYAH
(4)Std. InChI: InChI=1S/C13H11N3O5/c17-11-5-4-10(12(18)14-11)15-6-8-7(13(15)19)2-1-3-9(8)16(20)21/h1-3,10H,4-6H2,(H,14,17,18)
(5)Std. InChIKey: JKPJLYIGKKDZDT-UHFFFAOYSA-N

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