3-ETHYNYL-BENZOIC ACID Chemical Properties

Melting point:

164-171°C

Boiling point:

300.2±25.0 °C(Predicted)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

3.99±0.10(Predicted)

form 

powder

Appearance

White to off-white Solid

InChI

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

InChIKey

PHPIMLZTBYCDSX-UHFFFAOYSA-N

SMILES

OC(=O)c1cccc(c1)C#C

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-43

Safety Statements 

26-36/37/39

WGK Germany 

nwg

HS Code 

2916399090

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Irrit. 2
Skin Sens. 1

3-ETHYNYL-BENZOIC ACID Usage And Synthesis

Synthesis

Step 2: Methyl 3-((trimethylsilyl)ethynyl)benzoate (105) (2.42 g) was dissolved in methanol (30 mL), and 2N aqueous sodium hydroxide solution (10.4 mL) was slowly added under cooling in an ice bath, and the reaction was stirred at room temperature for 7 hours. After completion of the reaction, the pH of the reaction mixture was adjusted to 3~4 with 2N hydrochloric acid, followed by concentration under reduced pressure. Water (100 mL) was added to the residue and extracted with ethyl acetate (100 mL). The organic layer was washed with saturated brine (100 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 3-ethynylbenzoic acid (106) as a white solid (1.50 g, 99% yield).

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9562 - 9575
[2] Patent: JP5725475, 2015, B2. Location in patent: Paragraph 0028; 0031
[3] Patent: WO2014/168824, 2014, A1. Location in patent: Page/Page column 19

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