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

General Description

N-tert-butylmaleimide is a chemical compound with the molecular formula C9H13NO2. It is a white to off-white crystalline solid with a melting point of 94-98°C. N-tert-butylmaleimide is commonly used as a monomer for the synthesis of polymers and copolymers with various properties. It is also utilized as a cross-linking agent in the production of adhesives, coatings, and resins. Additionally, this compound has applications in the manufacturing of specialty chemicals, pharmaceuticals, and agrochemicals. N-tert-butylmaleimide should be handled and stored in a well-ventilated area and with proper protective equipment due to its potential health hazards.

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 

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.