10420-33-4

Basic information

• Product Name: Dimethyl acetylsuccinate
• Synonyms: acetyl-butanedioicaciddimethylester;acetyl-butanedioicacidimethylester;ACETYLSUCCINIC ACID DIMETHYL ESTER;DMAS;DIMETHYL ACETYLSUCCINATE;BUTANEDIOIC ACID, ACETYL-DIMETHYL ESTER;BUTANDIOIC ACID ACETYL-DIMETHYLESTER;Doimethyl Acetylsuccinate
• CAS NO: 10420-33-4
• Molecular Formula: C₈H₁₂O₅
• Molecular Weight: 188.18
• EINECS: 233-897-4
• Product Categories: Pharmaceutical Intermediates;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 10420-33-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 33 °C(lit.)
• Boiling Point: 129-134 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.16 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0118mmHg at 25°C
• Refractive Index: 1.43
• Storage Temp.: Store below +30°C.
• Solubility: 30g/l OECD Test Guideline 105
• PKA: 10.53±0.59(Predicted)
• Explosive Limit: 0.72-11.1%(V)
• CAS DataBase Reference: Dimethyl acetylsuccinate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl acetylsuccinate(10420-33-4)
• EPA Substance Registry System: Dimethyl acetylsuccinate(10420-33-4)

Safety Data

• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 10420-33-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 10420-33-4 differently. You can refer to the following data:
1. Dimethyl Acetylsuccinate was used in preparation of β-carbolines via diastereo- and enantioselective Bronsted acid catalyzed N-acyliminium cyclization cascades of tryptamines and keto acids/esters.
2. Dimethyl acetylsuccinate has been used in the synthesis of 2-oxofuro[2,3-b]pyrroles and 19-methyl-15-oxa-20-azatricyclo[12.3.3.0(1,14)]icos-18-en-18-carboxylates.

General Description

Dimethyl acetylsuccinate undergoes sulfuric acid catalyzed Pechmann condensation with the corresponding resorcinol derivative to give 7-hydroxycoumarins.

InChI:InChI=1/C8H12O5/c1-5(9)6(8(11)13-3)4-7(10)12-2/h6H,4H2,1-3H3

Upstream product

• 105-57-7 diethyl acetal 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 94-36-0 dibenzoyl peroxide 
• 123-63-7 paracetaldehyde 
• 108-24-7 acetic anhydride 
• 6141-58-8 methyl 2-methyl-3-furancarboxylate 
• 7039-93-2 2,5-Dihydrofuran-2,5-dimethoxy-2-methylfuran-3-carbonsaeuremethylester 
• 112799-49-2 5-Methoxy-2-methylfuran-3-carbonsaeuremethylester 
• 186581-53-3 diazomethane 
• 21634-63-9 methyl methyl-2-(1-methylethenyl)-2-hexenoate 
• 67-56-1 methanol 
• 107-25-5 methoxyethene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 70107-29-8 (+/-) 3-(methoxycarbonyl)-4-oxopentanoic acid 
• 123-76-2 levulinic acid 
• 5536-40-3 (2,6-dimethyl-4-hydroxy-pyrimidin-5-yl)-acetic acid 
• 681179-34-0 methyl (-)-(2S,3S)-2-methyl-5-oxotetrahydro-3-furancarboxylate 
• 681179-34-0 methyl (-)-(2S,3R)-2-methyl-5-oxotetrahydro-3-furancarboxylate 
• 681179-34-0 methyl cis-2-methyl-5-oxotetrahydro-3-furancarboxylate 
• 681179-34-0 methyl trans-2-methyl-5-oxotetrahydro-3-furancarboxylate 
• 433703-81-2 methyl 2-(7-hydroxy-4,8-dimethyl-2-oxo-2H-chromen-3-yl)acetate 
• 1451007-46-7 methyl 2-(2-([1,1′-biphenyl]-3-yl)-7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate 
• 1451007-30-9 methyl 2-(2-(3-(benzyloxy)phenyl)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate 
• 1451007-33-2 methyl 2-(2-(3-(benzyloxy)phenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate 
• 1451006-58-8 2-(2-(3-(benzyloxy)phenyl)-5-methyl-7-(4-methylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetic acid 
• 1451007-32-1 methyl 2-(2-(3-(benzyloxy)phenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate 
• 1451007-31-0 methyl 2-(2-(3-(benzyloxy)phenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate 

Relevant articles and documents

Alkoxycarbonylcarbene Transfer to Acyclic Tertiary Enaminones

Copper-catalyzed alkoxycarbonylcarbene transfer from methyl or tert-butyl diazoacetate to acyclic enaminoesters 6a,b and enaminocarboxanilide 13 yields vicinal push-pull-substituted cyclopropanes 7a,b, 8, and 14. In contact with dry silica gel, the latter compounds undergo facile ring-opening leading to enaminoesters 9,10, and 15. Treatment with aqueous acid transforms 9 and 10 into 2-acylsuccinates 11 and 12, and 15 into pyrrolinone 16. Methoxycarbonylcarbene transfer to enaminoketones 1a-c does not yield isolable cyclopropanes, but after hydrolytic work-up α-acyl-γ-ketoesters 2a-c are obtained.

4-(Phenylthio)-pyrrole-3-carboxylic Acid Esters

Dihydro(dimethoxy)methylfurancarboxylic acid esters 4A/4B have been applied to the synthesis of the title compounds.With amines as catalysts they react with thiophenols to give the addition products 12a-d, which upon heating with acids eliminate methanol to form the furancarboxylic acid esters 13a-b and 17, whereas reactions with ammonia or amines lead to the pyrrolecarboxylic acid esters 20a-e.Reactions of 4 with 2-aminothiophenol yield the fused pyrrole and pyrrolidine derivatives 15 and 16.Compounds 20b and e were transformed to the benzothiopyranopyrrole carboxylic acid esters 23a and b.