4-ETHYNYLBENZALDEHYDE

4-ETHYNYLBENZALDEHYDE Property

Melting point:

89-93 °C (lit.)

Boiling point:

223.8±23.0 °C(Predicted)

Density 

1.07±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

Powder or Crystalline Powder

color 

White to orange to brown

λmax

297nm(CH3CN)(lit.)

InChI

InChI=1S/C9H6O/c1-2-8-3-5-9(7-10)6-4-8/h1,3-7H

InChIKey

BGMHQBQFJYJLBP-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(C#C)C=C1

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-26-36

WGK Germany 

3

HS Code 

29122990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-ETHYNYLBENZALDEHYDE Chemical Properties,Usage,Production

Uses

4-?Ethynylbenzaldehyde is commonly used in solar cells as the acceptor unit.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 2280, 1981 DOI: 10.1021/jo00324a015

Synthesis

General procedure for the synthesis of 4-ethynylbenzaldehyde from 4-trimethylsilylethynylbenzaldehyde: Compound 4 (727 mg, 3.6 mmol) was dissolved in 15 mL of anhydrous THF, followed by the addition of 2 mL of aqueous KOH (298 mg, 4 mmol). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the THF solvent was removed by rotary evaporator. The reaction mixture was extracted with ethyl acetate (EA) and washed three times with saturated NaCl solution. The combined organic phases were dried with anhydrous Na2SO4, filtered and concentrated. Finally, purification by column chromatography (eluent was petroleum ether and dichloromethane, 1:1, v/v) gave 450 mg of compound 5 as a light yellow solid in 97% yield.

References

[1] Journal of the American Chemical Society, 2009, vol. 131, # 2, p. 634 - 643
[2] Chemical Communications, 2011, vol. 47, # 4, p. 1282 - 1284
[3] Journal of Materials Chemistry A, 2013, vol. 1, # 34, p. 10008 - 10015
[4] ChemPhysChem, 2016, p. 2066 - 2078
[5] Journal of the American Chemical Society, 2016, vol. 138, # 51, p. 16703 - 16710