4144-22-3

Basic information

• Product Name: N-TERT-BUTYLMALEIMIDE
• Synonyms: N-TERT-BUTYLMALEIMIDE;AKOS MSC-0047;N-tert-Butylmaleinimide;t-Butyl Maleimide;tert-Butylmaleimide;1-tert-Butyl-2,5-dihydro-1H-pyrrole-2,5-dione;1-(tert-Butyl)-1H-pyrrole-2,5-dione;N-tert-Butylmaleimide
• CAS NO: 4144-22-3
• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.18
• EINECS: 1533716-785-6
• Product Categories: API intermediates;Carbonyl Compounds;Cyclic Imides;Organic Building Blocks
• Mol File: 4144-22-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 62-64 °C
• Boiling Point: 189 °C(lit.)
• Flash Point: 176 °F
• Appearance: /
• Density: 1.059 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0831mmHg at 25°C
• Refractive Index: n20/D 1.477(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -2.18±0.20(Predicted)
• CAS DataBase Reference: N-TERT-BUTYLMALEIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-TERT-BUTYLMALEIMIDE(4144-22-3)
• EPA Substance Registry System: N-TERT-BUTYLMALEIMIDE(4144-22-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4144-22-3(Hazardous Substances Data)

Usage

Description

N-TERT-BUTYLMALEIMIDE, with the molecular formula C9H13NO2, is a white to off-white crystalline solid that exhibits a melting point of 94-98°C. It is a chemical compound known for its versatile applications in various industries, including polymer synthesis, adhesive production, and specialty chemical manufacturing.

Uses

Used in Polymer Synthesis:
N-TERT-BUTYLMALEIMIDE is used as a monomer for the synthesis of polymers and copolymers with diverse properties. Its unique structure allows for the creation of materials with tailored characteristics, making it a valuable component in the development of new polymeric materials.
Used in Adhesive Production:
In the adhesive industry, N-TERT-BUTYLMALEIMIDE serves as a cross-linking agent, enhancing the adhesive's strength and durability. Its ability to form covalent bonds with other molecules contributes to the improved performance of adhesives in various applications.
Used in Coating and Resin Manufacturing:
N-TERT-BUTYLMALEIMIDE is utilized in the production of coatings and resins, where it contributes to the formation of stable and robust coatings with desirable properties. Its cross-linking capabilities play a crucial role in the development of high-quality coatings and resins.
Used in Specialty Chemicals, Pharmaceuticals, and Agrochemicals:
N-TERT-BUTYLMALEIMIDE finds applications in the manufacturing of specialty chemicals, pharmaceuticals, and agrochemicals due to its reactive nature and ability to form stable compounds. Its versatility makes it a valuable component in the development of various chemical products.
Safety Precautions:
Due to its potential health hazards, N-TERT-BUTYLMALEIMIDE should be handled and stored in a well-ventilated area, and proper protective equipment should be used to minimize exposure risks.

InChI:InChI=1/C8H11NO2/c1-8(2,3)9-6(10)4-5-7(9)11/h4-5H,1-3H3

Upstream product

• 134276-00-9 N-tert-butyl maleamic acid 
• 108-31-6 maleic anhydride 
• 75-64-9 tert-butylamine 
• 32350-46-2 (Z)-4-(tert-butylamino)-4-oxo-2-butenoic acid 

Downstream Products

• 898262-99-2 (1R,3S,3aR,6aS)-3-(4-Bromo-phenyl)-5-tert-butyl-1-isobutyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrole-1-carboxylic acid 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecyl ester 
• 6622-05-5 1-(tert-butyl)pyrrolidine-2,5-dione 
• 1393661-22-7 N-(tert-butyl)-3-(phenoxymethyl)pyrrolidine-2,5-dione 

Relevant articles and documents

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.

Cavity-promoted Diels - Alder reactions of unsubstituted naphthalene: Fine reactivity tuning by cavity shrinkage

By finely tuning the cavity volume of a coordination cage, the Diels - Alder reactivity of aromatic compounds was enhanced. Even unsubstituted naphthalene could be made to undergo the Diels - Alder reaction with N-tert-butylmaleimide, with perfectly controlled syn-selectivity. M6L4 cages with standard and contracted cavities had opposite effects on the reaction: the former favored larger Diels - Alder substrates, whereas the latter favored smaller ones.

Chemical reactivity and antimicrobial activity of N-substituted maleimides

Several N-substituted maleimides containing substituents of varying bulkiness and polarity were synthesised and tested for antimicrobial and cytostatic activity. Neutral maleimides displayed relatively strong antifungal effect minimum inhibitory concentrations (MICs in the 0.54 g ml-1 range); their antibacterial activity was structure dependent and all were highly cytostatic, with IC50 values below 0.1 g ml-1. Low antimicrobial but high cytostatic activity was noted for basic maleimides containing tertiary aminoalkyl substituents. Chemical reactivity and lipophilicity influenced antibacterial activity of neutral maleimides but had little if any effect on their antifungal and cytostatic action. N-substituted maleimides affected biosynthesis of chitin and β(1,3)glucan, components of the fungal cell wall. The membrane enzyme, β(1,3)glucan synthase has been proposed as a putative primary target of N-ethylmaleimide and some of its analogues in Candida albicans cells.