591-60-6

Basic information

• Product Name: ACETOACETIC ACID N-BUTYL ESTER
• Synonyms: 3-oxo-butanoicacibutylester;acetoaceticacid,butylester;butyl3-oxobutyrate;butylesterkyselinyacetoctove;FEMA 2176;BUTYL 3-OXOBUTANOATE;BUTYL ACETOACETATE;ACETOACETIC ACID N-BUTYL ESTER
• CAS NO: 591-60-6
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.19
• EINECS: 209-722-2
• Product Categories: Organics
• Mol File: 591-60-6.mol
• Article Data: 57

Chemical Properties

• Melting Point: -35.6°C
• Boiling Point: 223.28°C (rough estimate)
• Flash Point: 85 °C
• Appearance: /
• Density: 0.98
• Vapor Pressure: 0.243mmHg at 25°C
• Refractive Index: 1.4250-1.4290
• PKA: 10.68±0.46(Predicted)
• CAS DataBase Reference: ACETOACETIC ACID N-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: ACETOACETIC ACID N-BUTYL ESTER(591-60-6)
• EPA Substance Registry System: ACETOACETIC ACID N-BUTYL ESTER(591-60-6)

Safety Data

• RTECS: AK5100000
• Hazardous Substances Data: 591-60-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid. Insoluble in water; solu- ble in alcohol and ether. Combustible.

Uses

Intermediate in synthesis of metal derivatives, dyestuffs, pharmaceuticals, flavoring.

Preparation

By heating butyl acetate and sodium or potassium butylate; from ethyl acetoacetate and n-butyl alcohol; by reacting diketene and butyl alcohol in the presence of acetic acid and pyridine.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 5400, 1953 DOI: 10.1021/ja01117a076

Safety Profile

Mddly toxic by ingestion. A skin and eye irritant. See also

InChI:InChI=1/C8H14O3/c1-3-4-5-11-8(10)6-7(2)9/h3-6H2,1-2H3

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 71-36-3 butan-1-ol 
• 123-86-4 acetic acid butyl ester 
• 2372-45-4 sodium butanolate 
• 3999-70-0 potassium n-butoxide 
• 141-97-9 ethyl acetoacetate 
• 1809-19-4 dibutyl hydrogen phosphite 
• 105-45-3 acetoacetic acid methyl ester 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 201230-82-2 carbon monoxide 
• 78-95-5 chloroacetone 
• 59557-05-0 (L)-menthyl 3-oxobutyrate 
• 1779-60-8 n-propyl acetoacetate 
• 10128-99-1 3-benzyl-6-methyl-[1,3]oxazine-2,4-dione 

Downstream Products

• 53605-94-0 n-butyl 3-hydroxybutyrate 
• 68999-91-7 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 2-benzyl ester 4-ethyl ester 
• 299406-89-6 butyl 2,7,7-trimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate 

Relevant articles and documents

The transacetoacetylation reaction: Mechanistic implications

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Br?nsted acidic cellulose-PO3H: An efficient catalyst for the chemoselective synthesis of fructones and trans-esterification via condensation of acetoacetic esters with alcohols and diols

Cellulose is the most abundant organic source and has expedient a great deal of interest as renewable and emerged as sustainable feedstock. The functionalization of cellulose as designed catalytic system intriguing furnished to the production of fine chemicals. Herein, we synthesized an environmental friendly solid acid catalyst by functionalizing cellulose with phosphoric acid (PO3H). The successful functionalization of cellulose with PO3H was confirmed by 31P NMR, ICP-OES, FE-SEM, and XPS analysis. ICP-OES revealed the presence of phosphorus content of ～1.0 wt. % on the catalyst's surface while elemental mapping by FESEM and XPS shows a uniform distribution of phosphorus over the material. The synthesized solid acid catalyst was utilized for condensation of diols with acetoacetic esters in solvent-free conditions to synthesize fine chemicals. The present approach not only circumvented the one-step protection and other products but more fascinatingly provided trans-esterification of acetoacetic esters with diols and n-alcohols. The catalyst was successfully used for chemoselective protection on ethyl acetoacetate with 1, 2 diols to essential fructone molecule with ～100% conversion and 99% selectivity. The results suggested that the catalyst has the advantage over commercial solid acid heterogeneous and homogeneous catalysts.

Preparation of mesoporous carbon nitride materials using urea and formaldehyde as precursors and catalytic application as solid bases

A series of mesoporous carbon nitride materials have been fabricated using inexpensive and eco-friendly urea and formaldehyde as precursors and mesocellular silica foam (MCF) as a template through a nanocasting approach. Several techniques, including XRD, TEM, elemental analysis, FT-IR, XPS, and CO2-TPD have been applied to characterize the physicochemical properties of the mesoCN materials, and the results show that the materials possess high surface areas (331–355?m2?g?1), relatively concentrated pore size of ca. 6?nm, and abundant and multiple nitrogen-containing species. As heterogeneous base catalysts, mesoCN materials demonstrate high catalytic activity and selectivity in both Knoevenagel condensation and transesterification reactions.