5164-76-1

Basic information

• Product Name: Dimethyl glutaconate
• Synonyms: DIMETHYL 2-PENTENOATE;DIMETHYL GLUTACONATE;2-Pentenedioic acid, dimethyl ester;(E)-2-Pentenedioic acid dimethyl ester;Glutaconic acid dimethyl ester;Nsc30046;DiMethyl pent-2-enedioate;DiMethyl Glutaconate (~10% Cis)
• CAS NO: 5164-76-1
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.15
• Mol File: 5164-76-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 192.8°Cat760mmHg
• Flash Point: >100 °C
• Appearance: /
• Density: 1.124 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.481mmHg at 25°C
• Refractive Index: n20/D 1.452
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• BRN: 1724169
• CAS DataBase Reference: Dimethyl glutaconate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl glutaconate(5164-76-1)
• EPA Substance Registry System: Dimethyl glutaconate(5164-76-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 5164-76-1(Hazardous Substances Data)

Usage

Description

Dimethyl glutaconate, also known as dimethyl 2-pentenoate, is a diester that is commonly utilized in the synthesis of various organic compounds. It is characterized by its ability to react with salicaldehyde in the presence of piperidine to form a coumarin-fused electron deficient diene. This unique property makes it a valuable intermediate in the chemical industry.

Uses

Used in Chemical Synthesis:
Dimethyl glutaconate is used as an intermediate in the synthesis of various organic compounds for several reasons. Its reactivity with salicaldehyde and piperidine allows for the formation of coumarin-fused electron deficient dienes, which are important in the creation of complex molecular structures.
Used in Pharmaceutical Industry:
Dimethyl glutaconate is used as a building block for the synthesis of phenanthridinone derivatives, which are known for their potential pharmaceutical applications. These derivatives have been studied for their biological activities, including potential use in the development of new drugs.
Used in Material Science:
In the field of material science, dimethyl glutaconate is used as a precursor for the synthesis of substituted benzenes. These substituted benzenes can be utilized in the development of new materials with specific properties, such as improved stability or enhanced reactivity.

InChI:InChI=1/C7H10O4/c1-10-6(8)4-3-5-7(9)11-2/h3-4H,5H2,1-2H3/b4-3-

Upstream product

• 67-56-1 methanol 
• 1724-02-3 glutaconic acid 
• 4126-54-9 dimethyl 3-methoxyglutaric acid 
• 13436-45-8 2-methoxytetrahydrofuran 
• 15243-33-1 dodecacarbonyl-triangulo-triruthenium 
• 1117-71-1 methyl 4-bromocrotonate 
• 1830-54-2 3-oxopentanedioic acid dimethyl ester 

Downstream Products

• 97661-19-3 2--glutarsaeure-dimethylester 
• 82522-94-9 1-(4-chloro-phenyl)-5-(4-chloro-phenylazo)-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid methyl ester 
• 16589-94-9 4-methoxycarbonylmethyl-2-methyl-6-oxo-tetrahydro-pyran-3-carboxylic acid ethyl ester 
• 16589-93-8 Methyl-β-methoxycarbonylmethyl-γ-aethoxycarbonyl-Δ^γ-δ-carboxylat 
• 16589-95-0 Dimethyl-β-(α'-ethoxycarbonyl-α'-hydroxymethylacetonyl)glutarate 
• 152327-57-6 dimethyl (E)-3-diazo-1-propene-1,3-carboxylate 
• 1346113-24-3 methyl (E)-3-(7-methoxy-2-oxo-2H-chromen-3-yl)acrylate 
• 1346113-25-4 3-methoxycarbonyl-2-methoxycarbonylmethyl-7-methoxy-2H-chromene 
• 1331741-00-4 C₁₇H₂₅N₆O₉P 
• 1331741-02-6 C₁₅H₂₁N₆O₉P 
• 77313-09-8 3-aminoglutaric acid dimethyl ester 
• 1408280-68-1 dimethyl 5-methylbiphenyl-2,4-dicarboxylate 
• 1408280-69-2 dimethyl 4'-chloro-5-methylbiphenyl-2,4-dicarboxylate 
• 1408280-70-5 dimethyl 4'-bromo-5-methylbiphenyl-2,4-dicarboxylate 

Relevant articles and documents

Selective esterification of nonconjugated carboxylic acids in the presence of conjugated or aromatic carboxylic acids under mild conditions

Nonconjugated carboxylic acids are selectively esterified in good yields in the presence of conjugated or aromatic carboxylic acids by stirring over Amberlyst-15 in alcohol at room temperature.

Rhodium-catalysed alkoxylation/acetalization of diazo compounds: One-step synthesis of highly functionalised quaternary carbon centres

An intermolecular tandem reaction for the rapid build-up of densely functionalised α-alkoxy-β-oxo-esters has been developed. This novel process applies the easy to handle trimethyl orthoformate as a C1-building block in the rhodium(ii)-catalysed alkoxylation/acetalization of donor-acceptor substituted diazo compounds. The concomitant C-O/C-C bond formation reaction gives products with unique quaternary carbon centers, substituted by groups of different oxidation level (ester, protected aldehyde and alkoxide).

Influence of functional substitution of allyl halides on their ni(co)4 promoted carbonylative cycloaddition with acetylenes

The effect of functional substitution of allyl halides on the outcome of the title reaction has been studied. Electron withdrawing and olefinic groups had different effects depending on their location. When they were placed at the central position of the allyl moiety carbonylative cycloaddition was found to be the main reaction, in acetone, to yield exclusively cyclohexenone (or aromatic) derivatives. In contrast, the same groups at the terminal site and in exteded conjugation with the allylic funtion were shown to favour competing side reactions such as allyl self-coupling. However, only cyclopentenones were obtained from either centrally or terminally substituted silylallyl halides. Substitution at both ends of the allyl moiety led to the formation of 4,5-disubstituted cyclopentenones. Important mechanistic information could be achieved from determination of the relative stereochemistry in these compounds.