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

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 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 105-45-3 acetoacetic acid methyl ester 
• 2911-21-9 2,4-dioxo-6-methyl-3,4-dihydro-2H-1,3-oxazine 
• 1694-31-1 tert-butyl acetoacetate 
• 93304-66-6 isopropenyl acetoacetate 
• 542-08-5 isopropyl acetoacetate 
• 7779-75-1 isobutyl acetoacetate 

Downstream Products

• 181863-03-6 2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid dibutyl ester 
• 1487-49-6 3-hydroxybutyric acid methyl ester 
• 24761-88-4 1-butyl diazoacetate 
• 59557-05-0 (L)-menthyl 3-oxobutyrate 
• 10196-33-5 3,3-bis(4'-hydroxy-3'-methyl-phenyl)butanoic acid n-butyl ester 
• 402514-80-1 butyl 4-(4-(benzyloxy)-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 61597-99-7 (S)-3-Hydroxybutansaeurebutylester 
• 82578-46-9 (R)-3-Hydroxybutansaeurebutylester 
• 53605-94-0 3-Hydroxy-butyric acid butyl ester 
• 18826-95-4 1.3-butanediol 
• 100875-65-8 3-phenylhydrazono-butyric acid butyl ester 
• 68999-91-7 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 2-benzyl ester 4-ethyl ester 
• 53605-94-0 n-butyl 3-hydroxybutyrate 

Relevant articles and documents

Visible-light-driven radical 1,3-addition of selenosulfonates to vinyldiazo compounds

Herein, we report a visible-light-driven radical 1,3-selenosulfonylation of vinyldiazo compounds with selenosulfonates, providing various γ-seleno allylic sulfones in good yields. This photochemical reaction was carried out at room temperature in an open flask using ethyl acetate as the solvent without any photocatalysts or additives. The control experiments corroborated that the 1,3-addition proceeded via a radical-chain propagation process. The synthetic applications of the resulting products were demonstrated by deselenization, reduction, bromination and allylation.

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.

N, N’-dimethyl formamide (DMF) mediated Vilsmeier–Haack adducts with 1,3,5-triazine compounds as efficient catalysts for the transesterification of β-ketoesters

N, N’-dimethyl formamide (DMF) mediated Vilsmeier–Haack (VH) adducts with 1,3,5-triazine compunds such as trichloroisocyanuric acid (TCCA) and trichlorotriazine (TCTA) were prepared by replacing classical oxy chlorides POCl3, and SOCl2, which were explored as efficient catalysts for the transesterification of β-ketoesters. The prepared (TCCA/DMF) and (TCTA/DMF) adducts improved greenery of the classical Vilsmeier–Haack reagents (POCl3/DMF), and (SOCl2/DMF), and demonstrated their better efficient catalytic ativity. Reaction times were in the range: 3.5 to 6.5 hr (SOCl2/DMF); 2.8–5.2 hr (POCl3/DMF); 2.5–5.2 hr (TCCA/DMF) and 2.5–5.0 hr (TCTA/DMF) catalytic systems. Ultrasonically (US) assisted protocols with these reagents further reduced the reaction times (two to three times), while microwave assisted (MW) protocols with these reagents were much more effective. The reactions could be completed in only few seconds (less than a minute) in MWassisted protocols as compared to US assited reactions, followed by good product yields.

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.

Copper-catalyzed radical coupling of 1,3-dicarbonyl compounds with terminal alkenes for the synthesis of tetracarbonyl compounds

A novel and efficient copper-catalyzed radical cross-coupling of 1,3-dicarbonyl compounds with terminal alkenes for the synthesis of tetracarbonyl compounds with a quaternary carbon atom has been developed. Mechanistically, this transformation involves the construction of two C-C bonds and two CO bonds in a one-pot process. The reaction tolerates a wide range of functional groups and proceeds under mild conditions.

Catalytic synthesis method for higher beta-ketoester

The invention relates to a reaction for synthesizing higher beta-ketoester by adopting NOMC (nitrogen-doped ordered mesoporous carbon) as a heterogeneous catalyst for catalyzing transesterification between simple beta-ketoester and alcohol. According to the reaction, NOMC is taken as the catalyst, beta-ketoester and alcohol are taken as the raw materials, the reaction is performed at the temperature of 90-110 DEG C for 4-6 h, and the highest yield of higher beta-ketoester can reach 97%. Compared with the conventional commonly-used homogeneous catalyst for the catalytic reaction, the reaction has the advantages that the catalyst is convenient to recover, the product is convenient to separate and the like.

3, 4, 5-tri-substituted oxazolidinone compounds and its preparation method (by machine translation)

The invention discloses a formula (I) of the structure shown in the 3, 4, 5? Tri-substituted oxazolidinone compound preparation method, the preparation method comprises: in the organic solvent, like type compound of the structure shown in the (II), of the structure shown in the formula (III) compound, organic base and the contact reaction mixture CuI, wherein R1 is selected from H, C1? C6 alkyl or nitro, R2 is selected from H or C1? C6 alkyl, R3 is selected from H, C1? C10 alkyl or vinyl. The steps of the preparation method is simple, is easy to obtain raw materials and catalyst, mild reaction conditions and high yield, (by machine translation)

Ag-Cu nanoparticles as efficient catalysts for transesterification of β-keto esters under acid/base-free conditions

Transesterification of β-keto esters and alcohols are traditionally catalyzed by acid or basic catalysts. However, these traditional catalysts do not always meet the requirements of modern synthetic chemistry which need to be highly efficient, selective, and environmentally friendly. In this work, Ag-Cu metal sites were first introduced as transesterification catalysts. The effect of the support, Ag:Cu molar ratio, and reaction conditions were investigated. The Ag-Cu metal sites were proved to be active in the β-ketoester transesterification with various alcohols, having yields comparable to the conventional acid- or base-catalysts.

METHOD FOR PRODUCING AN ALKYL 3-HYDROXYBUTYRATE

A method for making an alkyl 3-hydroxybutyrate is provided. The method can include reacting an alkyl alcohol with diketene to form an alkyl acetoacetate and then hydrogenating the alkyl acetoacetate to form the alkyl 3-hydroxybutyrate. The method of the present invention may also include separating one or more impurities an alkyl acetoacetate stream and subjecting the purified acetoacetate mixture to hydrogenation to form the alkyl 3-hydroxybutyrate. Methods of the present invention can be carried out on a lab, pilot, or commercial scale.

General and efficient transesterification of β-keto esters with various alcohols using Et3N as a br?nsted base additive

Transesterification of β-keto esters with a wide variety of allyl, benzyl, propargyl, and alkyl alcohols using, for the first time, commercially available and inexpensive Et3N as a Br?nsted base additive, is efficiently performed in toluene at reflux. The corresponding esters are exclusively obtained in 57-98% yields with no trace amounts of γ,δ-ketones, usually expected from the decarboxylative Carroll rearrangement.