51944-66-2

Basic information

• Product Name: 4-[(2E)-but-2-enoyl]morpholine
• Synonyms: Morpholine, 4-(1-oxo-2-butenyl)-
• CAS NO: 51944-66-2
• Molecular Formula: C₈H₁₃NO₂
• Molecular Weight: 155.1943
• Mol File: 51944-66-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 310.5°C at 760 mmHg
• Flash Point: 141.6°C
• Density: 1.059g/cm³
• Vapor Pressure: 0.000596mmHg at 25°C
• Refractive Index: 1.487
• CAS DataBase Reference: 4-[(2E)-but-2-enoyl]morpholine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(2E)-but-2-enoyl]morpholine(51944-66-2)
• EPA Substance Registry System: 4-[(2E)-but-2-enoyl]morpholine(51944-66-2)

Safety Data

• Hazardous Substances Data: 51944-66-2(Hazardous Substances Data)

Upstream product

• 110-91-8 morpholine 
• 623-43-8 crotonic acid methyl ester 
• 10487-71-5 crotonyl chloride 
• 100-39-0 benzyl bromide 
• 623-68-7 crotonic anhydride 
• 5327-51-5 (N-morpholin-4-yl)butan-1-one 
• 625-35-4 trans-chrotonyl chloride 

Downstream Products

• 108897-41-2 1-morpholino-2-phenylbutan-1-one 
• 96013-66-0 1-morpholino-3-phenylbutan-1-one 
• 1008762-70-6 C₂₈H₂₉NO₆ 
• 1008762-16-0 C₂₄H₂₃ClN₂O₅ 
• 86684-30-2 (1-Methyl-3-morpholin-4-yl-propyl)-(3-phenyl-isoxazol-5-yl)-amine 
• 86684-57-3 Benzyl-(1-methyl-3-morpholin-4-yl-propyl)-(3-phenyl-isoxazol-5-yl)-amine 

Relevant articles and documents

Bifunctional Iminophosphorane-Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α,β-Unsaturated Amides

The first metal-free catalytic intermolecular enantioselective Michael addition to unactivated α,β-unsaturated amides is described. Consistently high enantiomeric excesses and yields were obtained over a wide range of alkyl thiol pronucleophiles and elect

Chemoselective α,β-Dehydrogenation of Saturated Amides

We report a method for the selective α,β-dehydrogenation of amides in the presence of other carbonyl moieties under mild conditions. Our strategy relies on electrophilic activation coupled to in situ selective selenium-mediated dehydrogenation. The α,β-unsaturated products were obtained in moderate to excellent yields, and their synthetic versatility was demonstrated by a range of transformations. Mechanistic experiments suggest formation of an electrophilic SeIV species.

Microwave acceleration in DABAL-Me3-mediated amide formation

Facile direct coupling of esters and secondary amines to afford tertiary amides proceeds under microwave irradiation using the air-stable trimethylaluminium source DABAL-Me3 [(DABCO)(AlMe3)2]. Excellent yields (88-98%) are attained for cyclic secondary amines in reactions that are complete in 5-16 min. The process can be extended to the formation of Weinreb amides (upto 76% from commercial MeNHOMe·HCl) in a one-pot procedure using NaH to liberate the free methoxyamine.