Methyl 2-furoate Chemical Properties

Boiling point:

181 °C (lit.)

Density 

1.179 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.487(lit.)

FEMA 

2703 | METHYL 2-FUROATE

Flash point:

164 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear pale yellow to brown

Odor

fruity, mushroom-like odor

Odor Type

fungal

biological source

synthetic

Water Solubility 

slightly soluble

Sensitive 

Lachrymatory

JECFA Number

746

Merck 

14,4307

BRN 

111110

LogP

0.99

CAS DataBase Reference

611-13-2(CAS DataBase Reference)

NIST Chemistry Reference

Methyl 2-furoate(611-13-2)

EPA Substance Registry System

2-Furancarboxylic acid, methyl ester (611-13-2)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-21/22-22

Safety Statements 

26-36-36/37/39

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

3

RTECS 

LV1950000

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29321900

MSDS

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Methyl 2-furoate Usage And Synthesis

Description

Methyl 2-furoate has a pleasant, fruity odor similar to mushroom, fungus or tobacco with a sweet, tart, fruity taste that is quite heavy. May be prepared from 2-furoic acid in methanol solution in the presence of HCL as catalyst (oxidation or Carmizzaro reaction).

Chemical Properties

Methyl furoate has a pleasant, fruity odor similar to mushroom, fungus or tobacco with a sweet, tart, fruity taste that is quite heavy

Chemical Properties

Colorless to light yellow liqui

Occurrence

Reported found in cranberry, guava, baked potato, raisin, papaya, blackberry, baked potato, tomato, cognac, coffee, filbert, peanut, cocoa, passion fruit, almonds, tamarind, soursop, dried bonito, kiwifruit, mountain papaya, wild rice, okra, grape brandy and roasted hazelnut.

Uses

Solvent, organic synthesis.

Uses

Methyl 2-furoate (Methyl furan-2-carboxylate, Methyl pyromucate) was used to synthesize cis-fused 5-oxofuro[2,3-b]furans. It was also used in the preparation of sesquiterpene lactone.

Definition

ChEBI: Methyl 2-Furancarboxylate is a carboxylic ester. It is functionally related to a 2-furoic acid.

Preparation

From 2-furoic acid in methanol solution in the presence of HCl as catalyst (oxidation or Carmizzaro reaction)

Aroma threshold values

Aroma characteristics at 1.0%: musty, sweet caramel, fruity, cocoa, bready and slightly rubbery.

Taste threshold values

Taste characteristics at 20 ppm: brothy, yeasty, caramellic and burnt with a sweet bready, acetoin, buttery nuance

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 37, p. 3225, 1989 DOI: 10.1248/cpb.37.3225

General Description

Methyl 2-furoate has been identified as one of the volatile flavor compounds in tequila, okra, berrycactus and black currant juice.

Safety Profile

Poison by intraperitoneal route. A skin irritant and lachrymator. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

To a Schlenk tube equipped with a magnetic stirring bar, furoic acid (0.3 mmol), dimethyl malonate (1.8 mmol), KBr (0.09 mmol) and DMF (2 mL) were added sequentially. The reaction mixture was stirred at the set temperature for 12 hours. After the reaction was completed, the mixture was cooled to room temperature. The reaction solution was poured into ethyl acetate, washed with water and extracted with ethyl acetate. The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by fast column chromatography (eluent: petroleum ether or mixed solvent of petroleum ether/ethyl acetate) to obtain high purity methyl 2-furoate.

References

[1] Tetrahedron, 2015, vol. 71, # 48, p. 9067 - 9072

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