4-ETHYNYL-BENZOIC ACID Chemical Properties

Melting point:

200°C

Boiling point:

277.2±23.0 °C(Predicted)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

form 

powder or crystals

pka

3.95±0.10(Predicted)

color 

Light yellow to Yellow to Orange

InChI

InChI=1S/C9H6O2/c1-2-7-3-5-8(6-4-7)9(10)11/h1,3-6H,(H,10,11)

InChIKey

SJXHLZCPDZPBPW-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-36-22

Safety Statements 

26-36/37/39

HS Code 

2916399090

4-ETHYNYL-BENZOIC ACID Usage And Synthesis

Chemical Properties

4-Ethynylbenzoic acid is a bright yellow or orange solid at room temperature and pressure. It is a benzoic acid derivative and has the general properties of an acid.

Uses

4-Ethynylbenzoic acid may be used in the synthesis of N-(4-ethynylphenylcarbonyl) L-glutamic acid diethyl ester, a precursor for synthesizing glutamic acid-based dendritic helical poly(phenylacetylene)s. It can also be used to prepare zinc porphyrins attached to various cyclic aromatic hydrocarbon substituents, which can act as potential photo-sensitizers for dye-sensitized solar cells (DSSCs). This product was previously listed as CBR01612.

Synthesis

Synthesis of 4-ethynylbenzoic acid: Methyl 4-[(trimethylsilyl)ethynyl]benzoate (714 mg, 3.07 mmol) was dissolved in a methanol solution of 4% KOH (w:v, 30 mL) and the reaction was carried out at reflux overnight. Upon completion of the reaction, the pH of the reaction solution was adjusted to 2-3 with 6N HCl (detected by pH paper), followed by extraction with ethyl acetate (EtOAc) twice. The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to afford 4-ethynylbenzoic acid (427 mg, 2.92 mmol, 95% yield) as a brown solid.1H-NMR (d6-acetone, 500 MHz) δ (ppm): 7.62 (d, J = 16.2 Hz, 2H); 8.03 (d, J = 16.3 Hz 2H).

References

[1] Journal of the American Chemical Society, 2009, vol. 131, # 30, p. 10692 - 10700
[2] Patent: US2013/65248, 2013, A1. Location in patent: Page/Page column
[3] Patent: US9290791, 2016, B2
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4851 - 4856
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9562 - 9575

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