6141-58-8

Basic information

• Product Name: METHYL 2-METHYL-3-FUROATE
• Synonyms: 3-Furoic acid, 2-methyl-, methyl ester;Methyl 2-methylfuran-3-carboxylate;METHYL 2-METHYL-3-FURANCARBOXYLATE;METHYL 2-METHYL-3-FUROATE;AKOS BBS-00004384;2-METHYLFURAN-3-CARBOXYLIC ACID METHYL ESTER;Methyl 2-methylfurane-3-carboxylate;Methyl 2-methyl-3-furancarboxylate, GC 99%
• CAS NO: 6141-58-8
• Molecular Formula: C₇H₈O₃
• Molecular Weight: 140.14
• EINECS: 228-132-6
• Product Categories: Building Blocks;Furans;Heterocyclic Building Blocks
• Mol File: 6141-58-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 75 °C20 mm Hg(lit.)
• Flash Point: 147 °F
• Appearance: /
• Density: 1.116 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.1mmHg at 25°C
• Refractive Index: n20/D 1.473(lit.)
• Storage Temp.: 2-8°C
• BRN: 1342040
• CAS DataBase Reference: METHYL 2-METHYL-3-FUROATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-METHYL-3-FUROATE(6141-58-8)
• EPA Substance Registry System: METHYL 2-METHYL-3-FUROATE(6141-58-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 6141-58-8(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR YELLOW TO BROWN LIQUID

Uses

Methyl 2-methyl-3-furoate is a useful building block used in a variety of synthetic applications, such as the nickel-?catalyzed amide bond formation from methyl esters, and gold-catalyzed arylation by arylsilanes.

InChI:InChI=1/C7H8O3/c1-5-6(3-4-10-5)7(8)9-2/h3-4H,1-2H3

Upstream product

• 150437-92-6 methyl 5-(acetyloxy)-2-methyl-4,5-dihydrofuran-3-carboxylate 
• 24762-04-7 2-Diazo-3-oxo-butyric acid methyl ester 
• 109-92-2 ethyl vinyl ether 
• 108-05-4 vinyl acetate 
• 107-20-0 2-chloroethanal 
• 105-45-3 acetoacetic acid methyl ester 
• 1132772-82-7 cyanogenin D 3-O-β-D-cymaropyranosyl-(1->4)-α-L-diginopyranosyl-(1->4)-β-D-cymaropyranoside 
• 98837-36-6 methyl 3-hydroxy-2-methylenebutyrate 
• 67-56-1 methanol 
• 6947-94-0 2-methyl-3-furancarboxylic acid 
• 122889-56-9 spiro<5-carbomethoxy-4-methyl-7-oxabicyclo<2.2.1>hept-5-en-2-one-3,1'-cyclopropane> 

Downstream Products

• 81661-26-9 methyl 5-formyl-2-methyl-3-furancarboxylate 
• 345891-28-3 methyl 5‐bromo‐2‐methylfuran‐3‐carboxylate 
• 1254299-78-9 methyl 2-methyl-5-[4-(1-propionylaminoethyl)phenyl]furan-3-carboxylate 
• 5612-67-9 2-methyl-furan-3-carboxaldehyde 
• 345891-29-4 methyl 5-bromo-2-(bromomethyl)furan-3-carboxylate 
• 345891-27-2 methyl 5-bromo-2-(dibromomethyl)furan-3-carboxylate 
• 53020-08-9 2-bromomethylfuran-3-carboxylic acid methyl ester 
• 22727-22-6 2-methylfuran-3-carboxamide 
• 957346-10-0 5-bromo-2-[(4-methoxy-benzylamino)-methyl]-furan-3-carboxylic acid 
• 957346-08-6 5-bromo-2-[(4-methoxy-benzylamino)-methyl]-furan-3-carboxylic acid methyl ester 
• 957346-13-3 2-bromo-5-(4-methoxy-benzyl)-3a,5,6,6a-tetrahydro-furo[2,3-c]pyrrol-4-one 
• 24691-80-3 fenfuram 
• 444914-29-8 methyl 5-(4-fluorophenyl)-2-methylfuran-3-carboxylate 

Relevant articles and documents

Synthesis of furo[2,3-d]pyridazin-4(5h)-one and its N(5)-substituted derivatives

We report the efficient preparation of furo[2,3-d]pyridazin-4(5H)-one and its N-substituted derivatives starting from methyl 2-methylfuran-3-carboxylate. The Me group was converted to the aldehyde group, which was then condensed with hydrazine derivatives

Synthesis of Furans and Pyrroles from 2-Alkoxy-2,3-dihydrofurans Through a Nucleophilic Substitution-Triggered Heteroaromatization

An effective method to synthesize α-functionalized furan and pyrrole derivatives was developed using 2-alkoxy-2,3-dihydrofurans as modular precursors. This protocol featured a previously unreported tandem nucleophilic substitution/heteroaromatization reaction. Nucleophiles such as indole, α-oxoketene dithioacetal, trimethoxybenzene, and dimethoxynaphthalene can react readily with 2-alkoxy-2,3-dihydrofurans to afford α-functionalized five-membered ring heterocycles in the presence of acid catalysts, such as copper bromide and iron chloride. The mechanism of the reaction was also discussed, in which the first step, nucleophilic substitution, is the key in triggering the succeeding heteroaromatization. This method can also be extended to the synthesis of dihydrothiophenes.

A metathesis approach to aromatic heterocycles

The ring closing metathesis (RCM) reaction can be used to prepare substituted furans and pyrroles. By utilising a Pd-catalysed coupling reaction with methoxyallene, allylic alcohols and sulfonamides can be converted into substrates that are ideal precursors to ring closing metathesis. After the RCM reaction is complete, the addition of acid promotes an elimination of methanol to form the fully aromatised system. A range of different substitution patterns and functional groups are compatible with this sequence. Double allene coupling, RCM and elimination reactions are also possible and allow the formation of biaryl systems. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.