4271-99-2

Basic information

• Product Name: TRANS-ACONITIC ACID TRIMETHYL ESTER
• Synonyms: TRIMETHYL TRANS-ACONITATE;TRANS-ACONITIC ACID TRIMETHYL ESTER;Aconiticacidtrimethylester;(E)-1-Propene-1,2,3-tricarboxylic acid trimethyl ester;(E)-1-Propene-1,2,3-tris(carboxylic acid methyl) ester;trans-Aconitic acid trimethyl;TriMethyl (E)-Aconitate;(1E)-1-Propene-1,2,3-tricarboxylic Acid 1,2,3-TriMethyl Ester
• CAS NO: 4271-99-2
• Molecular Formula: C₉H₁₂O₆
• Molecular Weight: 216.19
• Product Categories: Aliphatics;Miscellaneous Reagents
• Mol File: 4271-99-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 160 °C / 20mmHg
• Flash Point: 90.1 °C
• Appearance: /
• Density: 1.22
• Refractive Index: 1.4620-1.4660
• Solubility: Chloroform, Dichloromethane, Ether
• CAS DataBase Reference: TRANS-ACONITIC ACID TRIMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-ACONITIC ACID TRIMETHYL ESTER(4271-99-2)
• EPA Substance Registry System: TRANS-ACONITIC ACID TRIMETHYL ESTER(4271-99-2)

Safety Data

• Hazardous Substances Data: 4271-99-2(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

Protected trans-Aconitic Acid.

Upstream product

• 146340-22-9 2-acetoxy-propane-1,2,3-tricarboxylic acid trimethyl ester 
• 6832-16-2 methyl diazoacetate 
• 2483-57-0 methyl 2-nitroacetate 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 67-56-1 methanol 
• 4023-65-8 trans-acotinic acid 
• 617-52-7 Dimethyl itakonate 
• 104310-17-0 (Z)-2-(2,2-Dichloro-vinyl)-but-2-enedioic acid dimethyl ester 
• 104310-15-8 methyl-3-methoxycarbonyl-3,5,5,5-tetrachloropentaneoate 
• 41505-91-3 methyl 2-(fluorosulfonyl)acetate 
• 96-32-2 bromoacetic acid methyl ester 
• 104310-21-6 6-chloro-4-methoxycarbonyl-2H-pyran-2-one 
• 201230-82-2 carbon monoxide 
• 19988-68-2 (Z)-2-Hydroxymethyl-but-2-enedioic acid dimethyl ester 

Downstream Products

• 95106-92-6 dimethyl 2-methoxycarbonylmethyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate 
• 95106-93-7 dimethyl 3-methoxycarbonylmethyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate 

Relevant articles and documents

A new, one pot synthesis of alkylated methyl tri- and tetracarboxylate derivatives by nitrolkanes

The reaction of nitroalkanes with trimethyl trans-aconitate in acetonitrile, in the presence of DBU as base, allows the one pot formation of alkylated methyl tri- and tetralkanoate derivatives via base induced nitrous acid elimination. The title compounds can also be obtained, in one flask, starting with the reaction of methyl nitroacetate with dimethyl maleate, followed by the addition, in the same flask of the nitroalkane.

A New Synthesis of Trimethyl Aconitate by Palladium-catalysed Triple Carbonylation of Propynyl Alcohol

A two-step palladium-catalysed carbonylation, consisting of an oxidative carbonylation of propynyl alcohol, followed by a substitutive carbonylation, leads to E and Z aconitic trimethyl esters in high yield.

A facile access to natural and unnatural dialkylsubstituted maleic anhydrides

A facile new route to the potential building blocks 2-bromomethyl-3-alkylmaleic anhydrides 15a/b for the synthesis of natural and unnatural dialkylsubstituted maleic anhydrides has been demonstrated, starting from dimethyl citraconate (9) via NBS-bromination, SN2′ Grignard coupling reactions, hydrolysis, molecular bromine addition and dehydrative ring closure reactions pathway with 49-51% overall yield in 5-steps. Chemoselective allylic substitution of bromoatom in 15a/b with Grignard reagents has been described to obtain the unsymmetrical maleic anhydride 16 and symmetrically dialkylsubstituted maleic anhydrides 25a/b in 55% yield. The naturally occurring 2-carboxymethyl-3-hexylmaleic anhydride (1) has been synthesized from 16 via esterification, ozonolysis and an oxidation route. The synthesis of two naturally occurring 2-(β-carboxyethyl)-3-alkylmaleic anhydrides 2a/b have been completed via a chemoselective diethylmalonate coupling reaction followed by acid induced hydrolysis. In our hands the SN2 or SN2′ coupling of Grignard reagent with 21 to obtain 1 and Reformatsky reaction with 15a/b to obtain 2c/d met with failure.