14826-58-5

Basic information

• Product Name: 1-(2-oxoazepan-1-yl)butane-1,3-dione
• CAS NO: 14826-58-5
• Molecular Formula: C₁₀H₁₅NO₃
• Molecular Weight: 197.231
• Mol File: 14826-58-5.mol

Chemical Properties

• Boiling Point: 348.8°C at 760 mmHg
• Flash Point: 158.4°C
• Density: 1.139g/cm³
• Vapor Pressure: 4.9E-05mmHg at 25°C
• Refractive Index: 1.487
• CAS DataBase Reference: 1-(2-oxoazepan-1-yl)butane-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-oxoazepan-1-yl)butane-1,3-dione(14826-58-5)
• EPA Substance Registry System: 1-(2-oxoazepan-1-yl)butane-1,3-dione(14826-58-5)

Safety Data

• Hazardous Substances Data: 14826-58-5(Hazardous Substances Data)

Usage

Chemical Structure

A cyclic ketone with a six-membered nitrogen-containing ring and two carbonyl groups on adjacent carbons

Appearance

Colorless to pale yellow liquid

Solubility

Soluble in water, ethanol, and most organic solvents

Boiling Point

205-206°C (401-404°F)

Density

1.02 g/cm3

Uses

Flavoring agent in the food industry, particularly in butter-flavored products such as microwave popcorn, margarine, and snack foods

Presence in E-cigarettes

Found in some e-cigarette liquids and other vaping products

Taste and Aroma

Creamy, buttery taste and aroma

Health Concerns

Linked to respiratory issues and lung disease, particularly in workers exposed to high levels of the chemical

Industry Response

Some manufacturers have started to phase out the use of diacetyl in their products due to health concerns

Upstream product

• 105-60-2 caprolactam 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 

Downstream Products

• 126686-08-6 C₂₀H₂₀N₂O₅ 
• 126686-08-6 4-acetyl-4,11a-epoxy-1,2,2a,4,5,7,8,9,10,11,11a,11b-dodecahydro-1,3,5-trioxo-2-phenyl-1H-pyrrolo<3,5-a>pyrido<1,2-a>azepine 
• 126686-08-6 4-acetyl-4,11a-epoxy-1,2,2a,4,5,7,8,9,10,11,11a,11b-dodecahydro-1,3,5-trioxo-2-phenyl-1H-pyrrolo<3,5-a>pyrido<1,2-a>azepine 

Relevant articles and documents

Catalytic asymmetric [3+2] cycloaddition of isomünchnones with methyleneindolinones

An efficient enantioselective [3+2] cycloaddition of isomünchnones with methyleneindolinones that are generated by anin situintramolecular addition of the carbonyl group to rhodium carbenes is realized with a chiralN,N′-dioxide/Zn(ii) complex as a Lewis acid. A series of chiral oxa-bridged 3-spiropiperidines are obtained in high yields with excellent dr and excellent ee values.

Synthesis of Nitrogen-Containing Polycycles via Rhodium(II)-Induced Cyclization-Cycloaddition and Insertion Reactions of N-(Diazoacetoacetyl)amides. Conformational Control of Reaction Selectivity

A series of diazoacetoacetamides, when treated with a catalytic quantity of a rhodium(II) carboxylate, were found to afford products derived from both a carbonyl ylide intermediate and intramolecular C-H insertion.With 3-(N-(diazoacetoacetyl)amino)propano

SYNTHESIS OF AZA SUBSTITUTED POLYCYCLES VIA RHODIUM (II) CARBOXYLATE INDUCED CYCLIZATION OF DIAZOIMIDES

Treatment of several substituted diazoimide derivatives with rhodium (II) carboxylates results in nitrogen-containing cyclic carbonyl ylide formation followed by 1,3-dipolar cycloaddition.

Synthesis of N-Acylacetoacetamide using 2,2,6-Trimethyl-1,3-dioxin-4-one

Diketene-acetone adduct (2,2,6-trimethyl-1,3-dioxin-4-one) 1 reacts with amide NH to give the corresponding N-acetoacetates 2.Formamide and basic amides such as picolinamide, on treatment with the adduct, are transformed to the N-acyl-2,6-dimethyl-4-oxo-4H-pyran-3-carboxamide (4a and 4p) together with the corresponding N-acetoacetates.Keywords--diketene-acetone adduct; 1,3-dioxin-4-one; acetylketene; diketene; acetoacetylation; 4-pyrone derivatives; N-acylacetoacetamide