Phenylpropiolic acid Chemical Properties

Melting point:

135-137 °C (lit.)

Boiling point:

225.74°C (rough estimate)

Density 

1.1674 (rough estimate)

refractive index 

1.5550 (estimate)

storage temp. 

2-8°C

form 

Fine Crystalline Powder

pka

pK1:2.269 (35°C)

color 

White to slightly beige

Water Solubility 

freely soluble

BRN 

742587

InChI

InChI=1S/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11)

InChIKey

XNERWVPQCYSMLC-UHFFFAOYSA-N

SMILES

C(O)(=O)C#CC1=CC=CC=C1

CAS DataBase Reference

637-44-5(CAS DataBase Reference)

NIST Chemistry Reference

Phenylpropiolic acid(637-44-5)

EPA Substance Registry System

2-Propynoic acid, 3-phenyl- (637-44-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

TSCA 

TSCA listed

HazardClass 

IRRITANT

HS Code 

29163900

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:Phenylpropiolic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Phenylpropiolic acid Usage And Synthesis

Chemical Properties

WHITE TO SLIGHTLY BEIGE FINE CRYSTALLINE POWDER

Uses

Phenylpropiolic Acid is used as a reagent in the high yield synthesis of 3,3-diphenylpropanoic acid derivatives via hydrophenylation and ionic hydrogenation with strong Lewis acids. It is also used in the synthesis of highly substituted aromatic rings via the alkyne-mediated approach which serve as templates for drug design.

Definition

ChEBI: An acetylenic compound that is propynoic acid in which the acetylenic hydrogen is replaced by a phenyl group.

Synthesis

Add phenylacetylene 6 mmol and ultra-dry tetrahydrofuran 25-30 mL in a 100 mL reaction flask, followed by evacuation treatment, N2 protection, put the reaction flask into an ethanol solution at -78??C, and then continue to add n-butyllithium 6 mmol, and after 1-1.5 h of reaction, access to a carbon dioxide balloon (inserted into the liquid level), and after 3-4 h of reaction, change the carbon dioxide balloon once again After 3-4 h of reaction, the reaction was replaced with another carbon dioxide balloon, and the reaction was carried out overnight. Afterwards, the reaction bottle was removed and stirred at room temperature to room temperature, 20mL of saturated ammonium chloride solution was added to the reaction bottle, and stirring was continued for 20-30 minutes. At the end of the reaction, it was first extracted with ether (2??20mL), and the aqueous phase was taken and the pH was adjusted to about 3 with dilute hydrochloric acid, and then ethyl acetate (2??20mL) was used, and the product phenylpropiolic acid was obtained by spin-drying at low pressure.

Purification Methods

Crystallise the acid from *benzene, CCl4 (m 136o) or aqueous EtOH. The S-benzylisothiuronium salt has m 184-186o (from EtOH). [Beilstein 9 II 436, 9 III 3061, 9 IV 2327.]

Phenylpropiolic acid(637-44-5)Related Product Information

• Propiolic Acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Hyaluronic acid
• Folic acid
• Propyne
• Ethyl propiolate
• Phenylacetylene
• Phenylpropyl aldehyde
• Phenylphosphonic dichloride
• Phenylphosphinic acid
• Phenylphosphonic acid
• Citric acid
• Ascoric Acid
• PHENYLPROPIOLIC ACID ETHYL ESTER,3-Phenylpropiolic acid ethyl ester,Phenylpropiolic acid ethyl
• PHENYLPROPIOLIC ACID METHYL ESTER,3-Phenylpropiolic acid methyl,Phenylpropiolic acid methyl
• Acetylene
• Phenylpropiolic acid
• P-TOLYL-PROPYNOIC ACID ETHYL ESTER