1073-93-4

Basic information

• Product Name: N-Isopropylmaleimide
• Synonyms: 1-isopropyl-3-pyrroline-2,5-quinone;1-propan-2-ylpyrrole-2,5-dione;1-(1-Methylethyl)-1H-pyrrole-2,5-dione;N-Isopropylmaleimide;1-Isopropyl-1H-pyrrole-2,5-dione
• CAS NO: 1073-93-4
• Molecular Formula: C₇H₉NO₂
• Molecular Weight: 139.15
• EINECS: 1533716-785-6
• Mol File: 1073-93-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 83 °C
• Boiling Point: 217.577 °C at 760 mmHg
• Flash Point: 88.854 °C
• Appearance: /
• Density: 1.177 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: 2-8°C
• PKA: -2.24±0.20(Predicted)
• CAS DataBase Reference: N-Isopropylmaleimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Isopropylmaleimide(1073-93-4)
• EPA Substance Registry System: N-Isopropylmaleimide(1073-93-4)

Safety Data

• Hazardous Substances Data: 1073-93-4(Hazardous Substances Data)

Usage

General Description

N-Isopropylmaleimide is a chemical compound with the molecular formula C7H9NO2. It is a white to off-white solid that is commonly used in the production of polymers and as a reagent in organic synthesis. N-Isopropylmaleimide is also used in the production of fluorescent dyes, adhesives, and coatings. It is known for its high thermal stability and its ability to undergo polymerization and copolymerization reactions. This chemical has potential applications in various fields, including the medical, agricultural, and industrial sectors. However, it is important to handle N-Isopropylmaleimide with care, as it can cause irritation to the skin, eyes, and respiratory system if proper precautions are not taken.

InChI:InChI=1/C8H9NO3/c1-6(10)7-2-4-8(5-3-7)9(11)12/h2-6,10H,1H3/t6-/m1/s1

Upstream product

• 108-31-6 maleic anhydride 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 75-31-0 isopropylamine 
• 6314-45-0 N-(isopropyl)maleamic acid 
• 541-59-3 maleiimide 
• 67-63-0 isopropyl alcohol 
• 617-48-1 malic acid 

Downstream Products

• 106475-43-8 3-(3-chloro-phenyl)-1-isopropyl-pyrrole-2,5-dione 
• 106474-65-1 3-(2-chloro-phenyl)-1-isopropyl-pyrrole-2,5-dione 
• 107623-17-6 3-(2,5-dichloro-phenyl)-1-isopropyl-pyrrole-2,5-dione 
• 27159-84-8 3-(2,4-dichloro-phenyl)-1-isopropyl-pyrrole-2,5-dione 
• 107517-04-4 1-isopropyl-3-(4-nitro-phenyl)-pyrrole-2,5-dione 
• 16213-16-4 1-isopropyl-3-phenyl-pyrrole-2,5-dione 
• 106272-38-2 1-isopropyl-3-(4-methoxy-phenyl)-pyrrole-2,5-dione 
• 106475-04-1 3-(2-bromo-phenyl)-1-isopropyl-pyrrole-2,5-dione 

Relevant articles and documents

1H and13C nuclear magnetic resonance studies of the hindered phencyclone adducts of some smaller branched N-alkyl maleimides: Rigorous aryl proton assignments with high-resolution two-dimensional (COSY45) spectroscopy, and anisotropic shielding effects and ab initio geometry optimizations

Phencyclone, 1, a potent Diels-Alder diene, reacts with a series of N-alkylmaleiniides, 2, to form hindered adducts, 3. The 300 MHz 1H and 75 MHz 13C NMR studies of these adducts at ambient temperatures have demonstrated slow rotations on the nuclear magnetic resonance (NMR) timescales for the unsubstituted bridgehead phenyl groups, and have revealed substantial magnetic anisotropic shielding effects in the 1H spectra of the N-alkyl groups of the adducts. The selected N-alkyl groups for the target compounds emphasized smaller branched alkyls, including C3 (isopropyl, a); C4 (isobutyl, b; and t-butyl, c); C5 (n-pentyl, d; isopentyl [isoamyl], e; 1-ethylpropyl, f; t-amyl, g;) and a related C8 isomer (1,1,3,3-tetramethylbutyl ["t-octyl"], h). The straight-chain n-pentyl analog was included as a reference. This present work on the branched N-al-kylmaleimide adducts appreciably extends our earlier compilation on the N-n-alkylmaleimide adducts. Key methods for proton assignments included "high-resolution" 1H-1H chemical shift correlation spectroscopy, COSY45. 13C NMR of the adducts, 3, verified the expected number of aryl carbons for slow exchange limit (SEL) spectra of the bridgehead phenyl groups. The synthetic routes involved reaction of the corresponding amines, 4, with maleic anhydride to give the N-alkylmaleamic acids, 5, which underwent cyclodehydration to form the maleimides, 2. Magnetic anisotropic shielding magnitudes for alkyl group protons in the adducts were calculated relative to corresponding proton chemical shifts in the maleimides. Geometry optimizations for the above adducts (and for the N-n-butylmaleimide adduct) were performed at the Hartree-Fock level with the 6-31G* basis set. The existence of different contributing conformers for the adducts is discussed with respect to their calculated energies and implications regarding experimentally observed anisotropic shielding magnitudes.

The Mitsunobu Reaction: A Novel Method for the Synthesis of Bifunctional Maleimide Linkers

Compounds 1-7 were synthesized from maleimide and the corresponding alcohols using a novel application of the Mitsunobu reaction.This procedure allows the direct formation of a variety of bifunctional linker compounds.

Cheap and efficient preparation method of benzene triimide and derivative thereof

The invention discloses a preparation method of benzene triimide (BTI) and a derivative thereof, wherein the structural general formula of the compound is represented by a formula I. The preparation method comprises the following steps: under the condition of refluxing in a mixed solution of acetic acid and water, carrying out an intermolecular aromatic ring construction reaction on a maleimide derivative represented by a formula II to obtain the benzene triimide (BTI) and the derivative I thereof. According to the invention, the cheap and easily available raw materials maleic anhydride and maleimide and the cheap and easily available primary amine compound are selected and subjected to simple addition, elimination and amination to rapidly prepare a large amount of maleimide derivatives, and further the maleimide derivatives are subjected to an intermolecular cyclization reaction to rapidly prepare the benzene triimide (BTI) and the derivative thereof in one step, so that the reactionconditions are mild, and the obtained product is stable in air and easy to separate and purify, and has good application prospect.

Novel 1-Heteroaryl-3-Azabicyclo[3.1.0]Hexanes Methods For Their Preparation And Their Use As Medicaments

The invention provides novel 1-heteroaryl-3-azabicyclo[3.1.0]hexanes, and related processes and intermediates for preparing these compounds, as well as compositions and methods employing these compounds for the treatment and/or prevention of central nervo