1874-23-3

Basic information

• Product Name: METHYL 5-NITRO-2-FUROATE
• Synonyms: RARECHEM AL BF 0008;2-Furancarboxylic acid, 5-nitro-, methyl ester;2-Furoic acid, 5-nitro-, methyl ester;5-nitro-2-furancarboxylicacimethylester;5-nitro-2-furoicacimethylester;Methyl 5-nitrofuroate;Methyl 5'-nitropyromucate;Methyl 5-nitropyromucate
• CAS NO: 1874-23-3
• Molecular Formula: C₆H₅NO₅
• Molecular Weight: 171.11
• EINECS: -0
• Product Categories: Esters;Furans, Benzofurans & Dihydrobenzofurans;Furans, Benzofurans & Dihydrobenzofurans;Building Blocks;Furans;Heterocyclic Building Blocks;Building Blocks;C4 to C7;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 1874-23-3.mol
• Article Data: 13

Chemical Properties

• Melting Point: 78-82 °C(lit.)
• Boiling Point: 301.06°C (rough estimate)
• Flash Point: 125.7°C
• Appearance: /
• Density: 1.6529 (rough estimate)
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.5423 (estimate)
• Storage Temp.: 2-8°C
• BRN: 165132
• CAS DataBase Reference: METHYL 5-NITRO-2-FUROATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 5-NITRO-2-FUROATE(1874-23-3)
• EPA Substance Registry System: METHYL 5-NITRO-2-FUROATE(1874-23-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• RTECS: LV2013000
• Hazardous Substances Data: 1874-23-3(Hazardous Substances Data)

Usage

Chemical Properties

yellowish crystalline powder

Uses

Methyl 5-nitro-2-furoate may be used in the synthesis of 5-nitro-2-furoylhydrazine and 5-nitro-2-furamide.

General Description

Methyl 5-nitro-2-furoate is a nitrofuran derivative. Its density, freezing point and refractive index have been evaluated. The reduction of methyl 5-nitro-2-furoate using milk xanthine oxidase has been reported to form methyl 5-hydroxylamino-2-furoate and methyl 5-amino-2-furoate. The utility of methyl 5-nitro-2-furoate as a matrix compound for matrix assisted ionization vacuum (MAIV) has been assessed using bovine insulin as an analyte.

InChI:InChI=1/C6H5NO5/c1-11-6(8)4-2-3-5(12-4)7(9)10/h2-3H,1H3

Upstream product

• 611-13-2 2-furoic acid methyl ester 
• 591-09-3 nitro acetate 
• 67-56-1 methanol 
• 645-12-5 5-nitro-2-furoic acid 
• 25084-14-4 5-nitrofuran-2-carboxylic chloride 
• 698-63-5 5-nitrofurane-2-carboxaldehyde 
• 88-14-2 2-furanoic acid 
• 555-15-7 5-nitrofuran-2-carboxaldehyde 
• 74-88-4 methyl iodide 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 57505-57-4 (Z)-methyl 2-acetoxy-5-nitro-2,5-dihydro-2-furancarboxylate 
• 94145-05-8 (5-Nitro-furan-2-yl)-[1,2,4]triazol-1-yl-methanone 

Downstream Products

• 174276-35-8 methyl 5-(2-benzyloxycarboxyphenoxy)-2-furancarboxylate 
• 174276-26-7 methyl 5-(2-carboxyphenylthio)-2-furancarboxylate 
• 99988-86-0 2-benzylmercapto-5-nitro-2,5-dihydro-furan-2-carboxylic acid 
• 100394-30-7 2-benzylmercapto-5-nitro-2,5-dihydro-furan-2-carboxylic acid methyl ester 
• 602280-12-6 methyl 5-[(1-benzyl-1H-indazol-3-yl)oxy]-2-furoate 
• 1145881-33-9 methyl 3-(cyclohex-2-enyl)-5-nitrofuran-2-carboxylate 
• 22600-30-2 methyl 5-amino-2-furoate 
• 83329-44-6 methyl 5-hydroxylamino-2-furoate 
• 80224-57-3 5-(2-Methoxycarbonyl-phenoxy)-furan-2-carboxylic acid methyl ester 
• 93104-97-3 5-o-Tolylsulfanyl-furan-2-carboxylic acid methyl ester 
• 93105-03-4 5-(4-Nitro-phenylsulfanyl)-furan-2-carboxylic acid methyl ester 
• 93105-02-3 5-(2-Amino-phenylsulfanyl)-furan-2-carboxylic acid methyl ester 
• 93105-01-2 5-(4-Chloro-phenylsulfanyl)-furan-2-carboxylic acid methyl ester 
• 93104-67-7 5-Benzylthio-2-furancarboxylic acid 

Relevant articles and documents

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A New Process for the Total Synthesis of Sparstolonin B

A novel and simple route was developed that gives sparstolonin B in high yields from affordable commercial compounds. A Diels-Alder strategy was used for the facile construction of the multisubstituted diphenyl ether. The xanthenone segment was obtained by cyclization in an intramolecular Friedel-Crafts reaction, followed by selective reduction of a ketone group and a transformation from a hydroxy group into a cyano group. The final part of the lactone was directly derived by the reduction of the cyano group with Raney nickel.

Rate-product correlations for the solvolysis of 5-nitro-2-furoyl chloride

The solvolysis rate constants of 5-nitro-2-furoyl chloride (5-NO 2(C4H2O)-2-COCl, 1) in 27 different solvents are well correlated with the extended Grunwald-Winstein equation, using the NT solvent nucleophilicity scale and YCl solvent ionizing scale, with sensitivity values of 1.20 ± 0.05 and 0.37 ± 0.02 for l and m, respectively. The activation enthalpies (ΔH≠) were 5.63 to 13.0 kcal·mol-1 and the activation entropies (ΔS ≠) were .25.9 to .43.4 cal·mol-1·K -1, which is consistent with the proposed bimolecular reaction mechanism. The solvent kinetic isotope effect (SKIE, kMeOH/kMeOD) of 2.65 was also in accord with the SN2 mechanism and was possibly assisted using a general-base catalysis. The product selectivity (S) for solvolysis of 1 in alcohol/water mixtures was 1.2 to 11, which is also consistent with the proposed bimolecular reaction mechanism.