60705-25-1

Basic information

• Product Name: Methyl 4,4-dimethoxyacetylacetate
• Synonyms: METHYL-4,4-(DIMETHOXY)ACETOACETATE;methyl 4,4-dimethoxyacetyl acetate;4,4-Dimthoxy-acetoaceticAcidMethylEster,4,4-Dimethoxy-3-oxo-butyricAcidMethylEster;Methyl-4,4-(Dimethoxy);Butanoicacid, 4,4-diMethoxy-3-oxo-, Methyl ester
• CAS NO: 60705-25-1
• Molecular Formula: C₇H₁₂O₅
• Molecular Weight: 176.16718
• Product Categories: All Aliphatics;Aliphatics;Miscellaneous Reagents
• Mol File: 60705-25-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 69-74°C / 1mm Hg
• Flash Point: 106.9 °C
• Appearance: colorless Liquid
• Density: 1.116 g/cm³
• Vapor Pressure: 0.0396mmHg at 25°C
• Refractive Index: 1.417
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 9.56±0.46(Predicted)
• CAS DataBase Reference: Methyl 4,4-dimethoxyacetylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4,4-dimethoxyacetylacetate(60705-25-1)
• EPA Substance Registry System: Methyl 4,4-dimethoxyacetylacetate(60705-25-1)

Safety Data

• Hazardous Substances Data: 60705-25-1(Hazardous Substances Data)

Usage

Description

Methyl 4,4-dimethoxyacetylacetate is an organic compound that is characterized as a colorless liquid. It is a derivative of acetylacetate, featuring two methoxy groups attached to the carbon adjacent to the ester group. This unique structure endows it with specific reactivity and properties that make it valuable in various chemical applications.

Uses

Used in Chemical Synthesis:
Methyl 4,4-dimethoxyacetylacetate is used as an intermediate in the synthesis of various organic compounds. Its ability to participate in Aldol condensations, a type of carbon-carbon bond-forming reaction, makes it a versatile building block for creating complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 4,4-dimethoxyacetylacetate is utilized as a key component in the synthesis of certain drugs. Its reactivity in Aldol condensations allows for the creation of novel drug candidates with potential therapeutic applications.
Used in Research and Development:
Methyl 4,4-dimethoxyacetylacetate is also employed in research and development settings, where it is used to explore new reaction pathways and develop innovative synthetic methods. Its high purity (greater than 95%) ensures that the reactions it participates in are reliable and reproducible, making it a valuable tool for scientists and researchers.

InChI:InChI=1/C7H12O5/c1-10-6(9)4-5(8)7(11-2)12-3/h7H,4H2,1-3H3

Upstream product

• 79-20-9 acetic acid methyl ester 
• 89-91-8 Methyl dimethoxyacetate 
• 6342-56-9 Pyruvic aldehyde dimethyl acetal 
• 616-38-6 carbonic acid dimethyl ester 
• 116273-92-8 methyl (E)-4,4-dimethoxy-3-(pyrrolidin-1-yl)but-2-enoate 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 74-88-4 methyl iodide 

Downstream Products

• 67448-15-1 (E,Z)-methyl 4,4-dimethoxy-2-(3-nitrobenzylidene)acetoacetate 
• 75530-05-1 4,4-Dimethoxy-2-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester 
• 160946-53-2 4,4-Dimethoxy-3-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 
• 177981-77-0 4,4-Dimethoxy-3-oxo-butyric acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 847372-41-2 methyl 3-(benzylamino)-4,4-dimethoxybutanoate 
• 75530-06-2 methyl 4,4-dimethoxy-2-(3-nitrobenzylidene)acetoacetate 
• 67448-02-6 methyl 2-(2-cyanobenzylidene)-4,4-dimethoxy acetoacetate 
• 75206-21-2 methyl 2-(2-cyanobenzylidene)-4,4-dimethoxyacetoacetate 
• 31925-25-4 7-E,9-E methyl trisporate B 
• 60705-22-8 Methyl 2-Dimethoxymethyl-1,3-dimethyl-4-oxocyclohex-2-enyl-1-carboxylat 
• 60705-21-7 Methyl 1,3-Dimethyl-2-formyl-4-oxocyclohex-2-enyl-1-carboxylat 
• 89845-12-5 methyl (5Z,10E)-11-benzoyloxy-8-((E)-2,2-dimethoxyethylidene)-9-oxo-5,10-undecadienoate 
• 78668-80-1 Benzoic acid 1-{(E)-2-[(2S,3R,4S,6R)-4-methanesulfonyloxy-6-(2-methoxycarbonyl-ethylsulfanyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-thiopyran-2-yl]-vinyl}-hexyl ester 
• 78668-68-5 Benzoic acid (Z)-2-(1-methanesulfonyloxy-2,2-dimethoxy-ethyl)-8-methoxycarbonyl-oct-4-enyl ester 

Relevant articles and documents

Reactions of pyrrolidine enamines of cyclic and acyclic 3,4-dioxobutanoic acid derivatives with dimethyl acetylenedicarboxylate. A new case of atropoisomerism

Reaction conditions and structure of the starting enamines (cyclic or open-chain) determine greatly the final products of the title reactions. Whereas in benzene and acetonitrile, DMAD and 1 give a mixture of the diastereoisomeric dienamines 5, in methanol they afford pirrolizine 3. Enaminofuranones 2 and 10 furnish in the corresponding 'Michael adducts' 7a,b,c and 11a,b,c but fail to yield pirrolizines. It has been demonstrated that above b and c adducts differ exclusively on the arrangement of groups around a chiral axis.

REACTIVIDAD DE ENAMINAS TERCIARIAS DE DERIVADOS CICLICOS Y DE CADENA ABIERTA DEL ACIDO 3,4-DIOXOBUTANOICO

Enaminoester 1a and enaminofuranone 2 with iodomethane, 2-chloro-1,3-dithiane and phenyldiazonium tetrafluoroborate afford the products resulting from electrophilic attack on the C-α to the carbonyl group.However, acyl chlorides with 1a yield O-acylated products.The above reactives and 1a give the corresponding products of enamino group hydrolysis.Enamines 1a and 1b react with dichlorocarbene, generated in phase transfer conditions, to yield chlorofuranones 17a and 17b dimethoxyacetamides 18a and 18b . p-Nitrophenylazide affords 1,2,3-triazol 20 in good yield by reaction with enaminoester 2; but when reacts with 2 gives in small amount the azoderivative 21.It is noteworthy that in the above cycloaddition reactions, the open-chained enaminoester 1a is much more reactive than the enaminofuranone 2.Palabras clave: Enaminoester, enaminolactona, alquilacion, acilacion, cicloadicion, diclorocarbeno, triazol.