| Identification | Back Directory | [Name]
4-ETHYNYLBENZALDEHYDE | [CAS]
63697-96-1 | [Synonyms]
Zinc02548316
CHEMBRDG-BB 4003406
4-ethynylbezaldehyde
4-ETHYNYLBENZALDEHYDE
Benzaldehyde,4-ethynyl-
4-Ethynylbenzaldehyde 97%
4-ETHYNYLBENZALDEHYDE,95%
4-Ethynylbenzaldehyde >
Benzaldehyde, 4-ethynyl- (9CI)
4-ethynylbenzaldehyde(SALTDATA: FREE)
4-ETHYNYLBENZALDEHYDE ISO 9001：2015 REACH | [Molecular Formula]
C9H6O | [MDL Number]
MFCD05664348 | [MOL File]
63697-96-1.mol | [Molecular Weight]
130.14 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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