5878-19-3

Basic information

• Product Name: Methoxyacetone
• Synonyms: 1-methoxy-2-propanon;1-Methoxy-2-propanone;1-Methoxyacetone;1-methoxypropan-2-one;CH3COCH2OCH3;Methoxymethyl methyl ketone;methoxymethylmethylketone;METHOXY-2-PROPANONE
• CAS NO: 5878-19-3
• Molecular Formula: C₄H₈O₂
• Molecular Weight: 88.11
• EINECS: 227-549-0
• Mol File: 5878-19-3.mol

Chemical Properties

• Melting Point: 78C
• Boiling Point: 118 °C(lit.)
• Flash Point: 77 °F
• Appearance: Clear pale yellow to yellow/Liquid
• Density: 0.957 g/mL at 25 °C(lit.)
• Vapor Pressure: 16.3mmHg at 25°C
• Refractive Index: n20/D 1.397(lit.)
• Storage Temp.: Flammables area
• Water Solubility: miscible
• BRN: 1560175
• CAS DataBase Reference: Methoxyacetone(CAS DataBase Reference)
• NIST Chemistry Reference: Methoxyacetone(5878-19-3)
• EPA Substance Registry System: Methoxyacetone(5878-19-3)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10
• Safety Statements: 16-29-33
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• RTECS: UC2988600
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 5878-19-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Methoxyacetone is used as a reagent in the bio-amination of ketones in organic solvents, which is a crucial step in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals. Its ability to facilitate this reaction makes it a valuable component in the field of organic chemistry.
Used in Synthesis of Doubly Borylated Enolates:
Methoxyacetone is also employed in the synthesis of doubly borylated enolates, which are important intermediates in organic chemistry. These enolates are used in various cross-coupling reactions and are key to the formation of complex molecular structures.
General Application:
The gas-phase basicity of methoxyacetone has been studied, which provides insights into its reactivity and potential applications in various chemical processes. Understanding its basicity can help chemists predict its behavior in different reaction conditions and optimize its use in various applications.

InChI:InChI=1/C4H8O2/c1-4(5)3-6-2/h3H2,1-2H3

Upstream product

• 107-98-2 1-methoxy-2-propanol 
• 1738-36-9 2-methoxyacetonitrile 
• 917-54-4 methyllithium 
• 625-45-6 2-methoxyacetic acid 
• 627-41-8 propargyl alcohol methyl ether 
• 186581-53-3 diazomethane 
• 107-31-3 Methyl formate 
• 1199-60-6 5-methoxy-4-oxo-4H-pyran-2-carboxylic acid 
• 7732-18-5 water 
• 6269-25-6 2-Hydroxymethyl-5-methoxy-4H-pyran-4-on 
• 99179-89-2 5,6-dimethoxy-4-oxo-4H-pyran-2-carboxylic acid methyl ester 
• 4780-14-7 3-methoxy-2-methyl-4-pyrone 
• 54620-66-5 5-methoxy-2-methoxymethyl-4H-pyran-4-one 
• 79-20-9 acetic acid methyl ester 

Downstream Products

• 52801-49-7 1-methoxy-2-methyl-4-phenyl-but-3-yn-2-ol 
• 42841-64-5 1-methoxy-2-methyl-but-3-yn-2-ol 
• 52801-48-6 4-cyclohex-1-enyl-1-methoxy-2-methyl-but-3-yn-2-ol 
• 107-98-2 1-methoxy-2-propanol 
• 6322-85-6 6-Methoxy-7H-benzocyclohepten-7-on 
• 64123-55-3 α³-Methoxy-N-(2-methoxy-1-methylaethyl)-2,6-dinitro-3,4-xylidin 
• 2109-96-8 2-Cyclohexyl-1-methoxy-propan-2-ol 
• 91968-77-3 1-Methoxy-2-(4-methylmercapto-phenyl)-propan-2-ol 
• 2109-94-6 2-(4-Fluor-benzyl)-1-methoxy-propan-2-ol 
• 64123-59-7 4-chloro-α-methoxy-N-(2-methoxy-1-methylethyl)-2,6-dinitro-m-toluidine 
• 2109-89-9 2-(4-chlorophenyl)-1-methoxypropan-2-ol 
• 2109-91-3 1-methoxy-2-(p-tolyl)propan-2-ol 
• 2109-87-7 2-Benzyl-1-methoxy-propan-2-ol 
• 2109-92-4 2-(4-Chlor-benzyl)-1-methoxy-propan-2-ol 

Relevant articles and documents

Bifunctional Catalysis of the Dedeuteration of Methoxyacetone-1,1,3,3,3-d5

The dedeuteration of methoxyacetone-1,1,3,3,3-d5 is subject to bifunctional catalysis by 3-(dimethylamino)-propylamine (3DP) and (1R,2S,3R,4R)-3-((dimethylamino)methyl)-1,7,7-trimethyl-2-norbornamine (DTN).These catalysts act by using their primary amino groups to transform the ketone to an iminium ion and their tertiary amino groups to transfer a deuteron internally, changing the iminium ion to an enamine.Although analogous monofunctional bases favor exchange at the methyl position relative to exchange at the methylene position by factors up to 4-fold, bifunctional catalysis by the diamines used favors the methyl group by 11- to 15-fold.Exchange at the methylene group in the presence of DTN was strongly stereoselective.The pro-S deuteron was removed 12-20 times as rapidly as the pro-R deuteron.This is the result of the steric effect of the methoxy substituent.

Kinetics and mechanism of oxidation of 1-methoxy-2-propanol and 1-ethoxy-2-propanol by Ditelluratocuprate(III) in alkaline medium

The kinetics of oxidation of 1-methoxy-2-propanol and 1-ethoxy-2-propanol by ditelluratocuprate(III) (DTC) in alkaline liquids has been studied spectrophotometrically in the temperature range of 293.2-313.2 K. The reaction rate showed first order dependence in DTC and fractional order with respect to 1-methoxy-2-propanol or 1-ethoxy-2-propanol. It was found that the pseudo-first order rate constant kobs increased with an increase in concentration of OH- and a decrease in concentration of TeO4 2-. There is a negative salt effect. A plausible mechanism involving a pre-equilibrium of a adduct formation between the complex and 1-methoxy-2-propanol or 1-ethoxy-2-propanol was proposed. The rate equations derived from mechanism can explain all experimental observations. The activation parameters along with the rate constants of the rate-determining step were calculated. The kinetics of oxidation of 1-methoxy-2-propanol and 1-ethoxy-2-propanol by ditelluratocuprate(III) (DTC) in alkaline liquids has been studied spectrophotometrically in the temperature range of 293.2-313.2 K. The reaction rate showed first order dependence in DTC and fractional order with respect to 1-methoxy-2-propanol or 1-ethoxy-2-propanol. It was found that the pseudo-first order rate constant kobs increased with an increase in concentration of OH- and a decrease in concentration of TeO 42-. A plausible mechanism of reaction was proposed. The activation parameters along with the rate-determining step have been also calculated.

Method for preparing methoxyacetone by using micro reaction device

The invention discloses a method for preparing methoxyacetone by using a microreaction device. The method comprises the following steps: mixing methanol with a basic catalyst to obtain a methanol solution; then pumping the methanol solution and epoxypropane into a micromixer in the microreaction device; sufficiently mixing and then introducing a mixed solution into a first microreactor in the microreaction device for reacting; after the reaction is ended, carrying out neutralizing and flash evaporation and concentration on a reaction solution to obtain 1-methoxy-2-propanol; pumping the 1-methoxy-2-propanol and an aqueous solution of sodium hypochlorite into a second microreactor in the microreaction device for reacting to obtain the methoxyacetone. According to the preparation method of the methoxyacetone, disclosed by the invention, the problems in the existing production can be overcome, the use of a complex catalyst is avoided, and the content of a byproduct is reduced; the production cost is low, the continuation degree of the process is high; the safety of the production process can be substantially improved; the quality of a product is improved.

Regio- and chemoselective rearrangement of terminal epoxides into methyl alkyl and aryl ketones

The development of the highly active pincer-type rhodium catalyst 2 for the nucleophilic Meinwald rearrangement of functionalised terminal epoxides into methyl ketones under mild conditions is presented. An excellent regio- and chemoselectivity is obtained for the first time for aryl oxiranes.

Method of synthesizing methoxyacetone through catalytic oxidation

The invention discloses a method of synthesizing methoxyacetone through catalytic oxidation. The method comprises the steps of mixing 1-methoxyl-2-propanol with sodium tungstate, tungstic acid and acetic acid, and raising temperature to 80-100 DEG C; adding hydrogen peroxide dropwise into the mixture, so as to obtain a reaction solution; naturally cooling the reaction solution to room temperature, and filtering and separating to obtain a filter cake and a filtrate; regulating pH of the filtrate to 6-7, transferring the filtrate into a rectifying tower and heating and rectifying, separating and purifying in a rectifying kettle to obtain a product methoxyacetone and residual liquid in the rectifying kettle; washing and drying the obtained filter cake to obtain tungstic acid; and mixing the residual liquid in the rectifying kettle and liquid caustic soda, raising temperature to dissolve and keeping warm, adding ethanol crystal, separating, and stoving to obtain the sodium tungstate. The catalyst is sodium tungstate that is low-cost, is easy to recycle, and causes low loss compared with other precious metal catalysts; in production, heavy metal contamination is prevented, fewer three wastes are generated, so that the method is environmentally friendly; and the conversion rate of 1-methoxyl-2-propanol reaches 93%, so that the method is suitable for industrial production.

Gas-Phase Reaction of Methyl n-Propyl Ether with OH, NO3, and Cl: Kinetics and Mechanism

Rate constants at room temperature (293 ± 2 K) and atmospheric pressure for the reaction of methyl n-propyl ether (MnPE), CH3OCH2CH2CH3, with OH and NO3 radicals and the Cl atom have been determined in a 100 L FEP-Teflon reaction chamber in conjunction with gas chromatography-flame ionization detector (GC-FID) as the detection technique. The obtained rate constants k (in units of cm3 molecule-1 s-1) are (9.91 ± 2.30) × 10-12, (1.67 ± 0.32) × 10-15, and (2.52 ± 0.14) × 10-10 for reactions with OH, NO3, and Cl, respectively. The products of these reactions were investigated by gas chromatography-mass spectrometry (GC-MS), and formation mechanisms are proposed for the observed reaction products. Atmospheric lifetimes of the studied ether, calculated from rate constants of the different reactions, reveal that the dominant loss process for MnPE is its reaction with OH, while in coastal areas and in the marine boundary layer, MnPE loss by Cl reaction is also important.

Method for synthesizing methoxy acetone

The invention belongs to the technical field of chemistry and chemical engineering, and particularly relates to a method for synthesizing methoxy acetone.The method is a catalytic oxidation method, and 1-methoxy-2-propyl alcohol, chlorohydrocarbon, a nitroxide free radical, sodium bicarbonate and trichloroisocyanuric acid are used as a raw material, solvent, a catalyst, an acid-binding agent and an oxidizing agent respectively to conduct a catalytic oxidation reaction.The reaction product is filtered after the reaction is completed, filter liquor is concentrated to recover solvent, and methoxy acetone is obtained through distillation.The 100% conversion rate of 1-methoxy-2-propyl alcohol in the reaction process can be nearly realized, the purity of methoxy acetone can reach 99.5% or more, the reaction condition is mild, and the synthetic method has industrial production prospects.

Method for preparing methoxyacetone by oxidizing 1-methoxy-2-propanol with chlorine

The invention belongs to the technical field of chemistry and chemical engineering and particularly relates to a method for preparing methoxyacetone by oxidizing 1-methoxy-2-propanol with chlorine.In a catalytic oxidation reaction, 1-methoxy-2-propanol serves as a raw material, hydrochloric ether serves as a solvent, the catalytic oxidation reaction is generated under catalysis of nitroxide and carbonate with chlorine as an oxidant, filtering is conducted after reaction, and after the filter solution is concentrated and the solvent is recycled, the product is obtained through distillation.In the reaction process, the conversion rate of 1-methoxy-2-propanol can be almost 100%, the purity of the product can reach 99.5% or above, and reaction conditions are mild.

Synthetic method for methoxyacetone

The invention belongs to the technical field of organic synthesis, and specifically relates to a synthetic method for methoxyacetone. The method comprises the following steps: subjecting propylene oxide and methanol to continuous reaction through a fixed-bed catalyst so as to obtain propylene glycol methyl ether; and mixing propylene glycol methyl ether with water, and carrying out continuous dehydrogenation reaction through the fixed-bed catalyst so as to obtain methoxyacetone. The synthetic method for methoxyacetone provided by the invention is scientific and reasonable, has simple process, is free of byproducts and contains less impurities.

Expanding Substrate Specificity of ω-Transaminase by Rational Remodeling of a Large Substrate-Binding Pocket

Production of structurally diverse chiral amines via biocatalytic transamination is challenged by severe steric interference in a small active site pocket of ω-transaminase (ω-TA). Herein, we demonstrated that structure-guided remodeling of a large pocket by a single point mutation, instead of excavating the small pocket, afforded desirable alleviation of the steric constraint without deteriorating parental activities toward native substrates. Molecular modeling suggested that the L57 residue of the ω-TA from Ochrobactrum anthropi acted as a latch that forced bulky substrates to undergo steric interference with the small pocket. Removal of the latch by a L57A substitution allowed relocation of the small pocket and dramatically improved activities toward various arylalkylamines and alkylamines (e.g., 1100-fold increase in kcat/KM for α-propylbenzylamine). This approach may provide a facile strategy to broaden the substrate specificity of ω-TAs.