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

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

Uses

Used in Polymer Production:
N-Isopropylmaleimide is used as a monomer in the production of polymers for its ability to undergo polymerization and copolymerization reactions, contributing to the development of materials with specific properties.
Used in Organic Synthesis:
As a reagent in organic synthesis, N-Isopropylmaleimide is utilized for its versatility in forming various chemical compounds, facilitating the creation of new materials and products.
Used in Fluorescent Dye Production:
N-Isopropylmaleimide is used as a precursor in the production of fluorescent dyes, which are essential in various applications such as bioimaging, diagnostics, and other scientific research areas.
Used in Adhesive and Coating Production:
This chemical compound is employed in the formulation of adhesives and coatings, leveraging its high thermal stability and reactivity to create durable and high-performance products.
Used in Medical Applications:
Although not explicitly mentioned in the provided materials, given its potential applications in various fields, N-Isopropylmaleimide could be utilized in the medical sector for specific purposes, such as in the development of drug delivery systems or as a component in certain pharmaceutical formulations.
Used in Agricultural Applications:
Similarly, while not detailed in the materials, the agricultural sector could benefit from N-Isopropylmaleimide in the development of new products, such as in the creation of pesticides or other agrochemicals.
Used in Industrial Applications:
N-Isopropylmaleimide's high thermal stability and reactivity make it suitable for use in various industrial applications, potentially including the manufacturing of high-performance materials and components for different industries.
It is crucial to handle N-Isopropylmaleimide with care due to its potential to cause irritation to the skin, eyes, and respiratory system if proper safety measures are not followed.

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

• 541-59-3 maleiimide 
• 67-63-0 isopropyl alcohol 
• 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 
• 617-48-1 malic acid 

Downstream Products

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

The discovery, design and synthesis of potent agonists of adenylyl cyclase type 2 by virtual screening combining biological evaluation

Adenylate cyclases (ACs), play a critical role in the conversion of adenosine triphosphate (ATP) into the second messenger cyclic adenosine monophosphate (cAMP). Studies have indicated that adenylyl cyclase type 2 (AC2) is potential drug target for many diseases, however, up to now, there is no AC2-selective agonist reported. In this research, docking-based virtual screening with the combination of cell-based biological assays have been performed for discovering novel potent and selective AC2 agonists. Virtual screening disclosed a novel hit compound 8 as an AC2 agonist with EC50 value of 8.10 μM on recombinant human hAC2 + HEK293 cells. The SAR (structure activity relationship) based on the derivatives of compound 8 was further explored on recombinant AC2 cells and compound 73 was found to be the most active agonist with the EC50 of 90 nM, which is 160-fold more potent than the reported agonist Forskolin and could selectively activate AC2 to inhibit the expression of Interleukin-6. The discovery of a new class of AC2-selective agonists would provide a novel chemical probe to study the physiological function of AC2.

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.

Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita

Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 ± 1.3, 5.1 ± 3.4, 16.2 ± 5.4, and 19.0 ± 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 ± 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at 50 mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.

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

NOVEL 1-ARYL-3-AZABICYCLO[3.1.0]HEXANES: PREPARATION AND USE TO TREAT NEUROPSYCHIATRIC DISORDERS

The invention provides novel, multiply-substituted l-aryl-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 nervous system (CNS) disorders, including depression and anxiety.

METHODS AND COMPOSITIONS FOR PRODUCTION, FORMULATION AND USE OF 1-ARYL-3-AZABICYCLO[3.1.0] HEXANES

The invention provides novel l-aryl-3-azabicyclo[3.1.0] hexanes that are active for modulating biogenic amine transport, along with compositions and methods for using these compounds to treat central nervous system disorders. Certain l-aryl-3-azabicyclo[3.1.0] hexanes are provided that have at least one substituent on the aryl ring. In other embodiments l-aryl-3-azabicyclo[3.1.0] hexanes are provided that have a substitution on the nitrogen at the '3' position. In additional embodiments l-aryl-3-azabicyclo[3.1.0] hexanes are provided which have one substitution on the aryl ring, as well as a substitution on the nitrogen at the '3' position. The invention also provides novel methods of making aryl- and aza-substituted l-aryl-3-azabicyclo[3.1.0] hexanes, including synthetic methods that form novel intermediate compounds of the invention for producing aryl- and aza-substituted l-aryl-3-azabicyclo[3.1.0] hexanes.

Synthesis and antimicrobial activities of N-substituted imides

In the field of our research programs concerning novel antimicrobial agents, a series of N-substituted imides was synthesized. These compounds were obtained by cyclization of amido-acids in acetic anhydride/sodium acetate or hexamethyldisilazane/zinc bromide for the hydroxy-aromatic derivatives. The hydroxy-alkyl maleimides were directly prepared by condensation of the corresponding amino-alcohol with maleic anhydride in boiling toluene. Most of N-substituted maleimides showed an interesting antimicrobial activity towards bacteria from the ATCC collection (Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) but the MIC values for P. aeruginosa were always high (128 μg/ml). The imides with alkyl substituents showed higher activities than aromatic analogues with MIC values in the range of 8-32 μg/ml. Comparatively, succinimides were practically inactive.