2028-33-3

Basic information

• Product Name: 2-(1-Methyl-2-oxopropyl)-1H-isoindole-1,3-(2H)-dione
• Synonyms: N-[3-BUTANONE(2)]-PHTHALIMIDE;2-(1-Methyl-2-Oxopropyl)-1h-Isoindole-1,3(2h)-Dione;N-(1-Methyl-2-oxopropyl)phthalimide
• CAS NO: 2028-33-3
• Molecular Formula: C₁₂H₁₁NO₃
• Molecular Weight: 217.22
• Mol File: 2028-33-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 85-86 °C
• Boiling Point: 345.3 °C at 760 mmHg
• Flash Point: 154.2 °C
• Appearance: white crystalline powder
• Density: 1.29 g/cm³
• Vapor Pressure: 6.21E-05mmHg at 25°C
• Refractive Index: 1.581
• PKA: -2.45±0.20(Predicted)
• CAS DataBase Reference: 2-(1-Methyl-2-oxopropyl)-1H-isoindole-1,3-(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-Methyl-2-oxopropyl)-1H-isoindole-1,3-(2H)-dione(2028-33-3)
• EPA Substance Registry System: 2-(1-Methyl-2-oxopropyl)-1H-isoindole-1,3-(2H)-dione(2028-33-3)

Safety Data

• Hazardous Substances Data: 2028-33-3(Hazardous Substances Data)

Usage

General Description

2-(1-Methyl-2-oxopropyl)-1H-isoindole-1,3-(2H)-dione, also known as N-Methylsuccinimide or NSI, is a chemical compound with the molecular formula C9H9NO3. It is a white to off-white crystalline solid with a slightly sweet odor. NSI is a cyclic imide and a derivative of succinic acid, and it is commonly used as a building block in organic synthesis. Its primary applications include the production of pharmaceuticals and agrochemicals, as well as a precursor in the synthesis of other chemical compounds. It is important to handle NSI with care, as it can be harmful if ingested or inhaled, and can cause skin and eye irritation.

InChI:InChI=1/C12H11NO3/c1-7(8(2)14)13-11(15)9-5-3-4-6-10(9)12(13)16/h3-7H,1-2H3

Synthetic route

potassium phtalimide (1074-82-4) + 3-bromo-butanone (814-75-5) → 2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3)

Conditions	Yield
at 20℃; for 0.233333h; Ionic liquid;	96%
In N,N-dimethyl-formamide at 20℃;

3-chloro-2-butanone (4091-39-8) + potassium phtalimide (1074-82-4) → 2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3)

Conditions	Yield
In N,N-dimethyl-formamide at 20 - 25℃; for 8h; Temperature;	95%
In N,N-dimethyl-formamide at 20℃;
In N,N-dimethyl-formamide at 20℃; for 3h;
In N,N-dimethyl-formamide at 20℃;

2-(2-hydroxy-1-methyl-propyl)-isoindole-1,3-dione → 2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3)

Conditions	Yield
With manganese(IV) oxide; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 2,6-Di-tert-butyl-1,4-benzoquinone In acetone at 65℃; for 17h; Temperature; Inert atmosphere;	80%

2-(1-methylallyl)isoindole-1,3-dione (7065-05-6) → 2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) + 2-(1,3-dioxoisoindolin-2-yl)butan-4-al (4667-80-5)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; silver(I) nitrite; copper(II) choride dihydrate; nitromethane; oxygen; tert-butyl alcohol at 20℃; under 760.051 Torr; for 6h; Wacker Oxidation;	A n/a B 79%

methyllithium (917-54-4) + 2-phthalimidopropionic acid (21860-84-4) → 2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3)

Conditions	Yield
In tetrahydrofuran; diethyl ether at -70 - 20℃; for 1h; Temperature;	62%

N-acetonylphthalimide (3416-57-7) + methyl iodide (74-88-4) → 2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide at 60℃; for 17h;

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → 3-Amino-2-butanone hydrochloride (21419-24-9)

Conditions	Yield
With hydrogenchloride In acetic acid Heating;

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → 2-hydroxymethyl-N-(2-hydroxy-1-methylpropyl)-benzamide

Conditions	Yield
With sodium borohydrid In aqueous propan-2-ol; water; acetic acid

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → D,L-1-bromo-3-phthalimido-2-butanone (70386-38-8)

Conditions	Yield
With bromine In water; acetic acid at 20℃;
With bromine; acetic acid at 20℃;

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C21H16N4O2S (1240790-62-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: bromine; acetic acid / 20 °C 2.1: ethanol / 20 °C 2.2: Reflux 3.1: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C21H20N4O6S (1240790-63-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: bromine; acetic acid / 20 °C 2.1: ethanol / 20 °C 2.2: Reflux 3.1: Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C20H15N5O2S (1240790-64-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C13H11N3O2S (1240790-65-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C19H15N3O2S (1240790-66-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C15H13N3O3S

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C20H15N3O3S

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C20H17N3O2S (1240790-69-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C25H19N3O2S (1240790-70-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C20H16N4O2S (1240790-71-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C19H15N5O2S (1240790-72-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / ethanol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C22H15NO3 (1240790-59-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: bromine; acetic acid / 20 °C 2.1: potassium carbonate / acetone / Reflux 2.2: Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C23H21NO7 (1240790-60-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: potassium carbonate / acetone / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → C17H13N3O2 (1240790-61-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; acetic acid / 20 °C 2: sodium hydrogencarbonate / butan-1-ol / Reflux View Scheme

2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3) → BrH*C13H12N4O2S

Conditions	Yield
Multi-step reaction with 2 steps 1.1: bromine; acetic acid / 20 °C 2.1: ethanol / 20 °C 2.2: Reflux View Scheme

Upstream product

• 3416-57-7 N-acetonylphthalimide 
• 74-88-4 methyl iodide 
• 4091-39-8 3-chloro-2-butanone 
• 1074-82-4 potassium phtalimide 
• 814-75-5 3-bromo-butanone 
• 53701-47-6 2-(1,3-dioxoisoindolin-2-yl)propanoyl chloride 
• 7065-05-6 2-(1-methylallyl)isoindole-1,3-dione 
• 917-54-4 methyllithium 
• 21860-84-4 2-phthalimidopropionic acid 
• 22509-74-6 N-ethoxycarbonylphthalimide 

Downstream Products

• 21419-24-9 3-Amino-2-butanone hydrochloride 
• 70386-38-8 D,L-1-bromo-3-phthalimido-2-butanone 
• 1240790-62-8 C₂₁H₁₆N₄O₂S 
• 1240790-64-0 C₂₀H₁₅N₅O₂S 
• 1240790-66-2 C₁₉H₁₅N₃O₂S 
• 1240790-69-5 C₂₀H₁₇N₃O₂S 
• 1240790-70-8 C₂₅H₁₉N₃O₂S 
• 1240790-71-9 C₂₀H₁₆N₄O₂S 

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