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

Chemical Properties

Colorless Liquid

Uses

Different sources of media describe the Uses of 60705-25-1 differently. You can refer to the following data:
1. Methyl 4,4-dimethoxyacetylacetate is useful for Aldol condensations.
2. Greater than 95 % pure. Useful for Aldol condensations.

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

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 
• 115550-28-2 methyl 2-hydroxymethyl-6-methyl-4-(2-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihyrdopyridine-3-carboxylate 
• 115550-26-0 methyl 2-formyl-6-methyl-4-(2-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylate 
• 115550-27-1 methyl 2-formyl-6-methyl-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-4-(2-trifluoromethylphenyl)-1,4-dihydropyridine-3-carboxylate 
• 115550-29-3 methyl 2-hydroxymethyl-6-methyl-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-4-(2-trifluoromethylphenyl)-1,4-dihydropyridine-3-carboxylate 
• 78668-67-4 Benzoic acid (Z)-2-(1-hydroxy-2,2-dimethoxy-ethyl)-8-methoxycarbonyl-oct-4-enyl ester 
• 78668-68-5 Benzoic acid (Z)-2-(1-methanesulfonyloxy-2,2-dimethoxy-ethyl)-8-methoxycarbonyl-oct-4-enyl ester 
• 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 
• 115550-24-8 Methyl 5-diallyloxyphosphinyl-2-dimethoxymethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate 
• 115569-94-3 methyl 2-dimethoxymethyl-6-methyl-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-4-(2-trifluoromethylphenyl)-1,4-dihydropyridine-3-carboxylate 
• 117966-29-7 5-(Bis-allyloxy-phosphoryl)-2-(hydroxyimino-methyl)-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl 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.