3249-68-1

Basic information

• Product Name: Ethyl butyrylacetate
• Synonyms: 3-oxo-hexanoicaciethylester;Ethyl alpha-butyrylacetate;Ethyl butyroacetate;3-KETOHEXANOIC ACID ETHYL ESTER;3-KETO-N-HEXANOIC ACID ETHYL ESTER;3-OXOHEXANOIC ACID ETHYL ESTER;AKOS 220-93;BUTYRYLACETIC ACID ETHYL ESTER
• CAS NO: 3249-68-1
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.19
• EINECS: 221-835-9
• Product Categories: Pharmaceutical Intermediates;BUILDING BLOCKS;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks
• Mol File: 3249-68-1.mol
• Article Data: 42

Chemical Properties

• Melting Point: -44°C
• Boiling Point: 104 °C22 mm Hg(lit.)
• Flash Point: 173 °F
• Appearance: Clear colorless/Liquid
• Density: 0.989 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.243mmHg at 25°C
• Refractive Index: n20/D 1.427(lit.)
• Storage Temp.: Store below +30°C.
• PKA: 10.69±0.46(Predicted)
• Water Solubility: IMMISCIBLE
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 507689
• CAS DataBase Reference: Ethyl butyrylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl butyrylacetate(3249-68-1)
• EPA Substance Registry System: Ethyl butyrylacetate(3249-68-1)

Safety Data

• Safety Statements: 24/25
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• RTECS: MO8420500
• Hazardous Substances Data: 3249-68-1(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 3249-68-1 differently. You can refer to the following data:
1. colourless liquid
2. Ethyl 3-oxohexanoate has a slightly fatty odor.

Uses

Ethyl Butyrylacetate is used in the synthesis of pharmaceutical agents such as the anti-HIV agent (+/-)-Calanolide A.Also used in the synthesis of potent and selective polymerase inhibitors.

Taste threshold values

Taste characteristics at 50 ppm: fruity, pineapple and green with sweet licorice and vanilla notes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 310, 1979 DOI: 10.1021/jo01316a039

General Description

Ethyl 3-oxohexanoate is a volatile flavor ester that is reported to occur in banana fruit. It can undergo bioreduction to form ethyl (R)-3-hydroxyhexanoate, another key food flavoring agent.

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

Upstream product

• 1071-46-1 hydrogen ethyl malonate 
• 141-75-3 butyryl chloride 
• 73295-48-4 ethyl 2-diazo-3-hydroxyhexanoate 
• 2033-24-1 cycl-isopropylidene malonate 
• 64-17-5 ethanol 
• 74-96-4 ethyl bromide 
• 141-97-9 ethyl acetoacetate 
• 72546-06-6 5-butanoyl-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 955404-45-2 C₈H₁₁F₃O₃ 
• 30410-63-0 α-Hydroxy-β-nitro-n-capronsaeure-aethylester 
• 41115-60-0 1-(1H-benzo[d][1,2,3]triazol-1-yl)butan-1-one 
• 109-74-0 propyl cyanide 
• 105-36-2 ethyl bromoacetate 
• 52194-43-1 Z-β-Nitro-hexen-(2)-saeure-aethylester 

Downstream Products

• 59663-70-6 ethyl 3-aminocaproate 
• 41340-09-4 (7-methoxy-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid 
• 14994-18-4 1.4-Bis-<1-hydroxy-3-oxo-hexyl>-benzol 
• 57816-83-8 (8-ethyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid 
• 13505-35-6 Undecandion-(4,8) 
• 72817-86-8 4-Amino-5-cyan-3-ethyl-salicylsaeure-ethylester 
• 85111-47-3 2-ethyl-3,5,5-trimethylcyclohex-2-en-1-one 
• 52452-41-2 4-Ethoxy-3-ethyl-6-methyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 
• 92494-37-6 3-(2-chloro-phenyl)-5-propyl-isoxazole-4-carboxylic acid ethyl ester 
• 67187-93-3 (E)-3-(4-Acetylamino-2,5-dimethoxy-phenylamino)-hex-2-enoic acid ethyl ester 
• 92029-30-6 3-phenyl-5-propyl-isoxazole-4-carboxylic acid 
• 93735-65-0 N-Aethyl-N-<4-oxo-heptyl>-phenaethylamin 
• 1747-59-7 3-propyl-isoxazole-4,5-dione 4-o-tolylhydrazone 
• 2305-25-1 3-hydroxy-hexanoic acid ethyl ester 

Relevant articles and documents

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Discrimination of β-ketoesters by ruthenium(II)-binap-catalyzed asymmetric hydrogenation

(Chemical Equation Presented) Please, after you... β-Ketoesters in mixtures underwent Noyori reduction one by one at room temperature under 4 bar of hydrogen pressure in the presence of a catalyst formed from RuII and (S)-binap (see example). The rate of the asymmetric hydrogenation and hence the selectivity for a particular β-ketoester was found to depend on the Lewis basicity of the ester group. Binap = 2,2′-bis(diphenylphosphanyl)-1, 1′-binaphthyl.

Radical Aza-Cyclization of α-Imino-oxy Acids for Synthesis of Alkene-Containing N-Heterocycles via Dual Cobaloxime and Photoredox Catalysis

Nitrogen-containing heterocycles are prevalent in both naturally and synthetically bioactive molecules. We report herein an unprecedented protocol for radical aza-cyclization of α-imino-oxy acids with pendant alkenes via synergistic photoredox and cobaloxime catalysis. With or without alkenes as the intermolecular cross-coupling partners, the transformation provides a variety of corresponding alkene-containing dihydropyrrole products in satisfactory yields. In the presence of external alkenes, the tandem reaction generates E-selective coupling products with excellent chemo- and stereoselectivity.

Synthesis of Long-Chain β-Lactones and Their Antibacterial Activities against Pathogenic Mycobacteria

In the quest for new antibacterial agents, a series of novel long- and medium-chain mono- and disubstituted β-lactones was developed. Their activity against three pathogenic mycobacteria—M. abscessus, M. marinum, and M. tuberculosis—was assessed by the resazurin microtiter assay (REMA). Among the 16 β-lactones synthesized, only 3-hexadecyloxetan-2-one (VM005) exhibited promising activity against M. abscessus, whereas most of the β-lactones showed interesting activities against M. marinum, similar to that of the classical antibiotic, isoniazid. Regarding M. tuberculosis, six compounds were found to be active against this mycobacterium, with β-lactone VM008 [trans-(Z)-3-(hexadec-7-en-1-yl)-4-propyloxetan-2-one] being the best growth inhibitor. The promising antibacterial activities of the best compounds in this series suggest that these molecules may serve as leads for the development of much more efficient antimycobacterial agents.

Continuous flow synthesis of toxic ethyl diazoacetate for utilization in an integrated microfluidic system

An integrated microfluidic system for multiple reactions and separations of hazardous ethyl diazoacetate is presented. The integrated techniques include: a droplet technique for liquid-liquid and/or gas-liquid separation and in situ generation of the toxic reagent, a dual channel membrane technique based on a cheap polymeric microseparator for liquid-liquid separation, and a capillary microreactor for carrying out cascade reactions in a sequential and continuous manner.