2-Benzofurancarboxaldehyde Chemical Properties

Melting point:

9-9.5 °C

Boiling point:

135 °C18 mm Hg(lit.)

Density 

1.206 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.633(lit.)

FEMA 

3128 | 2-BENZOFURANCARBOXALDEHYDE

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Liquid

Specific Gravity

1.206

color 

Clear yellow to brown

Odor

at 100.00 %. bitter almond

Odor Type

fruity

Water Solubility 

Not miscible or difficult to mix with water.

Sensitive 

Air Sensitive

JECFA Number

751

BRN 

2910

LogP

2.09

CAS DataBase Reference

4265-16-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzofuran-2-carboxaldehyde(4265-16-1)

EPA Substance Registry System

2-Benzofurancarboxaldehyde (4265-16-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29329990

MSDS

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

2-Benzofurancarboxaldehyde Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Chemical Properties

2-Formyl benzofuran has a bitter almond odor.

Uses

Benzo[b]furan-2-carboxaldehyde is used for the synthesis of isoxazolines.

Uses

2-Benzofurancarboxaldehyde may be used in the preparation of (E)-3-(benzofuran-2′-ylmethylidene)-1-methyl-2-indolinone and 1-(benzofuran-2-yl)methanol.

Preparation

By the Gattermann process; also from coumaryloyl cyanide.

Definition

ChEBI: 2-Benzofurancarboxaldehyde is a member of benzofurans.

General Description

2-Benzofurancarboxaldehyde, also known as benzo[b]-2-furfural, is an α,β-unsaturated aldehyde.

Synthesis

General procedure for the synthesis of benzo[b]furan-2-carbaldehyde from 2,3-benzofuran and N,N-dimethylformamide: Triclosan (4.73 mL, 50.79 mmol) was slowly added to a solution of N,N-dimethylformamide (6.56 mL, 84.75 mmol) under conditions of keeping the temperature lower than 40 °C. Subsequently, 2,3-benzofuran (2.00 g, 16.93 mmol) was added dropwise to the reaction mixture over a period of 15 min under the same temperature conditions. The reaction mixture was heated up to 80 °C for 24 hours. After completion of the reaction, the mixture was carefully poured into ice water and neutralized with sodium hydroxide solution. The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the resulting crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 10:1) to afford benzo[b]furan-2-carbaldehyde (2.27 g, 90% yield) as a brown oil.1H NMR (400 MHz, CDCl3): δ 9.83 (1H, s, CHO), 7.75-7.70 (1H, m, H-4 ), 7.56-7.54 (2H, m, H-6,7), 7.46 (1H, s, H-3), 7.32-7.28 (1H, m, H-5).13C NMR (100 MHz, CDCl3): δ 179.63 (CHO), 156.03 (C-7a), 152.52 (C-2), 129.07 (C-3a) , 126.51 (C-6), 124.05 (C-5), 123.58 (C-4), 117.93 (C-3), 112.44 (C-7).

References

[1] Chemical Communications, 2017, vol. 53, # 54, p. 7545 - 7548
[2] Organic Letters, 2012, vol. 14, # 3, p. 844 - 847
[3] Letters in Drug Design and Discovery, 2014, vol. 11, # 8, p. 975 - 984
[4] ChemMedChem, 2017, vol. 12, # 3, p. 257 - 270
[5] Patent: WO2016/114816, 2016, A1. Location in patent: Paragraph 0331

2-Benzofurancarboxaldehyde(4265-16-1)Related Product Information

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