31110-30-2

Basic information

• Product Name: (2Z)-but-2-enamide
• Synonyms: 2-Butenamide, (2Z)-
• CAS NO: 31110-30-2
• Molecular Formula: C₄H₇NO
• Molecular Weight: 85.1045
• Mol File: 31110-30-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 100-101 °C
• Boiling Point: 218.7°C at 760 mmHg
• Flash Point: 86°C
• Density: 0.956g/cm³
• Vapor Pressure: 0.124mmHg at 25°C
• Refractive Index: 1.456
• PKA: 15.78±0.50(Predicted)
• CAS DataBase Reference: (2Z)-but-2-enamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z)-but-2-enamide(31110-30-2)
• EPA Substance Registry System: (2Z)-but-2-enamide(31110-30-2)

Safety Data

• Hazardous Substances Data: 31110-30-2(Hazardous Substances Data)

Upstream product

• 625-37-6 crotonamide 
• 124-38-9 carbon dioxide 
• 1190-76-7 (Z)-2-butenenitrile 

Downstream Products

• 15856-96-9 (Z)-pent-2-enamide 
• 625-37-6 crotonamide 

Relevant articles and documents

Ru-Based Catechothiolate Complexes Bearing an Unsaturated NHC Ligand: Effective Cross-Metathesis Catalysts for Synthesis of (Z)-α,β-Unsaturated Esters, Carboxylic Acids, and Primary, Secondary, and Weinreb Amides

Despite notable progress, olefin metathesis methods for preparation of (Z)-α,β-unsaturated carbonyl compounds, applicable to the synthesis of a large variety of bioactive molecules, remain scarce. Especially desirable are transformations that can be promoted by ruthenium-based catalysts, as such entities would allow direct access to carboxylic esters and amides, or acids (in contrast to molybdenum-or tungsten-based alkylidenes). Here, we detail how, based on the mechanistic insight obtained through computational and experimental studies, a readily accessible ruthenium catechothiolate complex was found that may be used to generate many α,β-unsaturated carbonyl compounds in up to 81% yield and ≥98:2 Z/E ratio. We show that through the use of a complex bearing an unsaturated N-heterocyclic carbene (NHC) ligand, for the first time, products derived from the more electron-deficient esters, acids, and Weinreb amides (vs primary or secondary amides) can be synthesized efficiently and with high stereochemical control. The importance of the new advance to synthesis of bioactive compounds is illustrated through two representative applications: An eight-step, 15% overall yield, and completely Z-selective route leading to an intermediate that may be used in synthesis of stagonolide E (vs 11 steps, 4% overall yield and 91% Z, previously), and a five-step, 25% overall yield sequence to access a precursor to dihydrocompactin (vs 13 steps and 5% overall yield, formerly).

METHOD FOR PRODUCING CARBOXYLIC ACID AMIDE

A carboxamide can be produced in a high yield by a method for producing a carboxamide, for example, represented by formula (4): (wherein R1 and R3 are as defined below), the method comprising a step of allowing a carboxylic acid ester represented by formula (1): (wherein R1 represents an optionally substituented C1-C20 hydrocarbon group or an optionally substituented C3-C20 heterocyclic group, and R2 represents an optionally substituented C1-C20 hydrocarbon group), an amine represented by formula (2): [in-line-formulae]R3—NH2 ??(2)[/in-line-formulae] (wherein R3 represents a hydrogen atom or an optionally substituented C1-C20 hydrocarbon group), and a formamide compound represented by formula (3): (wherein R3 is as defined above) to react in the presence of a metal alkoxide.