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

Uses

Dimethyl glutaconate may be used in the synthesis of:dimethyl 3-[(Z)-1-propenyl]glutaratephenanthridinone derivativessubstituted benzenes

General Description

Dimethyl glutaconate, also known as dimethyl 2-pentenoate, is a diester. It reacts with salicaldehyde in the presence of piperidine to form a coumarin-fused electron deficient diene.

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

Downstream Products

• 146445-27-4 4-methoxycarbonyl-non-3-en-8-ynoate de methyle 
• 185420-79-5 2-(2-Methoxycarbonyl-1-methoxycarbonylmethyl-ethyl)-4,4-dimethyl-3-oxo-pentanoic acid methyl ester 
• 82522-87-0 2-(4-chloro-phenylazo)-4-(4-chloro-phenylhydrazono)-pentenedioic acid dimethyl ester 
• 216690-15-2 dimethyl 3-(4-fluorophenyl)glutarate 
• 99902-23-5 Dimethyl(1α,4α,5α)-7-oxobicyclo<3.3.0>oct-2-ene-2,4-dicarboxylate 
• 99902-22-4 dimethyl (E)-4-(4-oxo-2-cyclopentenyl)glutaconate 
• 1173452-22-6 (3R,4R,5S)-2-tert-butyl 4-methyl 3-benzyl-5-(2-methoxy-2-oxoethyl)isoxazolidine-2,4-dicarboxylate 
• 1173452-25-9 (3S,4R,5S)-2-tert-butyl 4-methyl 5-(2-methoxy-2-oxoethyl)-3-phenylisoxazolidine-2,4-dicarboxylate 
• 1173452-26-0 (3S,4R,5S)-2-tert-butyl 4-methyl 3-(4-bromophenyl)-5-(2-methoxy-2-oxoethyl)isoxazolidine-2,4-dicarboxylate 
• 1173452-38-4 (3R,4R,5S)-2-benzyl 4-methyl 3-isobutyl-5-(2-methoxy-2-oxoethyl)isoxazolidine-2,4-dicarboxylate 
• 1173452-40-8 (3R,4R,5S)-2-benzyl 4-methyl 3-isopropyl-5-(2-methoxy-2-oxoethyl)isoxazolidine-2,4-dicarboxylate 
• 1173452-41-9 (3R,4R,5S)-2-benzyl 4-methyl 3-cyclohexyl-5-(2-methoxy-2-oxoethyl)isoxazolidine-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).

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In the presence of a palladium(0) complex and potassium t-butoxide, the acetylenic compounds 2 bearing in δ a nucleophilic functionality are smoothly transformed with excellent yields, either into 2,2-difunctionalized methylene cyclopentanes or into monofunctionalized 2-methylcyclopentenes. Each of these compounds can be specifically obtained depending on the choice of the experimental conditions. A set of diverse reactions involving mainly potassium hydride as the base showed clearly that HPdOtBu is not the active catalytic species which is mainly a σ-ethynylpalladium hydride formed by the metal insertion in the acetylenic carbon hydrogen bond.