ETHYL 5-(CHLOROMETHYL)-2-FURANCARBOXYLATE Chemical Properties

Boiling point:

115 °C0.015 mm Hg(lit.)

Density 

1.225 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.511(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Liquid

Specific Gravity

1.225

color 

Clear yellow

CAS DataBase Reference

2528-00-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

38

Safety Statements 

37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29321900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

ETHYL 5-(CHLOROMETHYL)-2-FURANCARBOXYLATE Usage And Synthesis

Chemical Properties

clear yellow liquid

Uses

Ethyl 5-(chloromethyl)-2-furancarboxylate may be employed for the synthesis of a series of novel sulfamide- and urea-based small-molecule antagonists of the protein-protein interaction IL-2/IL-2Rα. It may be employed as starting material for the synthesis of 5-hydroxymethylfuran-2-carboxylic acid.

Synthesis

Volatiles were removed by distillation under reduced pressure at room temperature and the crude product 5-(chloromethyl)-2-furancarbonyl chloride (4, 2.90 g) was dissolved in anhydrous ethanol (20 mL). The resulting clarified yellow solution was reacted at 50 °C with continuous stirring for 6 hours. Upon completion of the reaction, the solvent was removed by rotary evaporator and the resulting residue was purified by column chromatography using dichloromethane/hexane (1:1 to 3:1 gradient) as eluent to afford the target product, ethyl 5-(chloromethyl)furan-2-carboxylate (5), as a colorless oil (2.390 g, 82% yield). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3) and 13C NMR (75 MHz, CDCl3): 1H NMR δ 7.06 (d, J = 3.5 Hz, 1H), 6.44 (d, J = 3.5 Hz, 1H), 4.55 (s, 2H), 4.31 (q, J = 7.1 Hz, 2H), 1.32 (t, J = 7.1 Hz, 3H); 13C NMR δ 158.35, 153.96, 145.02, 118.54, 111.37, 61.10, 36.68, 14.26.

References

[1] Green Chemistry, 2015, vol. 17, # 7, p. 3737 - 3739
[2] Patent: WO2016/191682, 2016, A1. Location in patent: Paragraph 0045

ETHYL 5-(CHLOROMETHYL)-2-FURANCARBOXYLATE(2528-00-9)Related Product Information

• METHYL 5-(CHLOROMETHYL)-2-FUROATE
• ETHYL 5-(CHLOROMETHYL)-2-FURANCARBOXYLATE
• METHYL 5-METHYL-2-FUROATE
• 2-Chloromethylfuran
• 5-CHLOROMETHYL-FURAN-2-CARBOXYLIC ACID ISOPROPYL ESTER
• 5-Chloromethylfurfural
• METHYL FUROATE
• ETHYL 2-FUROATE
• ETHYL 5-(1-CHLOROETHYL)-2-FUROATE