7779-75-1

Basic information

• Product Name: Isobutyl acetoacetate
• Synonyms: 3-Oxobutanoic acid isobutyl ester;3-Oxobutyric acid isobutyl ester;Acetoacetic acid 2-methylpropyl ester;Isobutyl Acetoacetate, 98.0%(GC);3-oxo-butanoicaci2-methylpropylester;Isobutyl 3-oxobutanoate;ACIB;ACETOACETIC ACID ISOBUTYL ESTER
• CAS NO: 7779-75-1
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.19
• EINECS: 231-937-5
• Product Categories: Organics;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 7779-75-1.mol
• Article Data: 22

Chemical Properties

• Melting Point: 177-179 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 100 °C22 mm Hg(lit.)
• Flash Point: 173 °F
• Appearance: clear/
• Density: 0.98 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.342mmHg at 25°C
• Refractive Index: n20/D 1.424(lit.)
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 10?+-.0.46(Predicted)
• BRN: 1761405
• CAS DataBase Reference: Isobutyl acetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Isobutyl acetoacetate(7779-75-1)
• EPA Substance Registry System: Isobutyl acetoacetate(7779-75-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 7779-75-1(Hazardous Substances Data)

Usage

Description

Isobutyl acetoacetate has a sweet, winey, brandy-like odor and a sweet and slightly fruity flavor. May be prepared from isobutyl acetate by heating in the presence of sodium isobutylate.

Chemical Properties

Different sources of media describe the Chemical Properties of 7779-75-1 differently. You can refer to the following data:
1. Isobutyl acetoacetate has a sweet, winy, brandy-like odor and a sweet and slightly fruity flavor.
2. Clear liquid

Uses

Different sources of media describe the Uses of 7779-75-1 differently. You can refer to the following data:
1. Isobutyl acetoacetate is used as intermediate for the production of pharmaceuticals (e.g. Nisoldipine). Product Data Sheet
2. Isobutyl Acetoacetate is a building block that has been used as a reactant in the preparation of b-annulated 1,4-dihydropyridine derivatives as TGFβ signaling inhibitors.

Preparation

From isobutyl acetate by heating in the presence of sodium isobutylate.

InChI:InChI=1/C8H14O3/c1-6(2)5-11-8(10)4-7(3)9/h6H,4-5H2,1-3H3

Upstream product

• 78-83-1 2-methyl-propan-1-ol 
• 105-45-3 acetoacetic acid methyl ester 
• 674-82-8 4-methyleneoxetan-2-one 
• 625-44-5 isobutyl methyl ether 
• 72324-39-1 5-acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 141-97-9 ethyl acetoacetate 
• 85920-63-4 5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 57654-60-1 Bis-isobutyloxycarbonylmethyl-quecksilber 
• 75-36-5 acetyl chloride 
• 2343-88-6 Acetoacetylfluorid 
• 123-86-4 acetic acid butyl ester 
• 110-19-0 2-methylpropyl acetate 
• 13259-29-5 sodium isobutoxide 

Downstream Products

• 52937-90-3 2-methyl-1-propyl 3-amino-2-butenoate 
• 111556-88-8 isobutyl methyl 2,6-dimethyl-4-<2-(trifluoromethyl)phenyl>-1,4-dihydropyridine-3,5-dicarboxylate 
• 111556-89-9 isobutyl methyl 2,6-dimethyl-4-<3-(trifluoromethyl)phenyl>-1,4-dihydropyridine-3,5-dicarboxylate 
• 50639-30-0 isobutyl 2-diazoacetate 
• 27944-79-2 2,4-dimethylpentanal 
• 110-19-0 2-methylpropyl acetate 
• 67-64-1 acetone 
• 115-11-7 isobutene 
• 147597-26-0 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid monoisobutyl ester 
• 111634-72-1 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-methylpropyl ester 
• 5396-89-4 benzyl acetoacetate 

Relevant articles and documents

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.

A synthetic method of an m-nisoldipine medicine intermediate isobutyl acetoacetate

A synthetic method of an m-nisoldipine medicine intermediate isobutyl acetoacetate is disclosed. The method includes adding 10.6 mol of methyl iso-butyl ether and 3-3.2 mol of methylamine into a reactor provided with a stirrer, a thermometer, a reflux condenser and a dropping funnel, controlling the stirring speed to be 160-190 rpm, raising the temperature of the solution to 85-90 DEG C, adding dropwise 10.6-10.8 mol of diketene (2) while maintaining the reaction temperature to be 85-88 DEG C with the addition time being controlled to be 4-5 h, refluxing for 4 h after the addition is finished with the reaction solution being brown, cooling the solution until the temperature of the solution is 35-40 DEG C, washing with a salt solution, dehydrating with a dehydrating agent, performing vacuum distillation, and collecting a distillate at 109-115 DEG C to obtain the isobutyl acetoacetate (1). The mass percentage of the methylamine is 65-70%.

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.