3-Hydroxyphenylacetylene Chemical Properties

Melting point:

64-66 °C

Boiling point:

75°C 3mm

Density 

1.083 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.5840(lit.)

Flash point:

218 °F

storage temp. 

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

solubility 

Miscible with dimethylformamide.

pka

9.30±0.10(Predicted)

form 

Crystalline Powder

color 

White to pale yellow

BRN 

2076613

InChI

InChI=1S/C8H6O/c1-2-7-4-3-5-8(9)6-7/h1,3-6,9H

InChIKey

AODMJIOEGCBUQL-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

10401-11-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41-52/53

Safety Statements 

26-37/39

RIDADR 

2810

WGK Germany 

2

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

29071990

MSDS

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

3-Hydroxyphenylacetylene Usage And Synthesis

Chemical Properties

Clear yellow liquid

Uses

3-Hydroxyphenylacetylene is used as a fluorogenic and chromogenic probe for bacterial enzymes.

Synthesis

The general procedure for the synthesis of 3-hydroxyphenylacetylene from (3-hydroxyphenylalkynyl)trimethylsilane was as follows: (3-hydroxyphenylalkynyl)trimethylsilane was dissolved in a mixed solvent of THF (6 mL) and MeOH (6 mL), followed by the addition of 10% aqueous KOH solution (6 mL). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction mixture was neutralized with 1N HCl solution and the solvent was subsequently removed by rotary evaporation. The aqueous phase was extracted with CH2Cl2 and the organic phase was dried with anhydrous Na2SO4. Finally, purification by column chromatography (eluent: n-hexane/acetone, 5:1, v/v) afforded 3-hydroxyphenylacetylene (162.8 mg, 70% yield), the product was a yellow oil.

References

[1] Patent: US2009/68242, 2009, A1. Location in patent: Page/Page column 7
[2] Organic Letters, 2014, vol. 16, # 24, p. 6302 - 6305

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