1-PHENYL-2-PROPYN-1-OL Chemical Properties

Melting point:

22-23 °C(lit.)

Boiling point:

135-136 °C13 mm Hg(lit.)

alpha 

0°(neat)

Density 

1.087 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.549(lit.)

Flash point:

211 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

12.40±0.20(Predicted)

form 

Liquid

Specific Gravity

1.087

color 

Clear yellow

BRN 

742365

InChIKey

UIGLAZDLBZDVBL-UHFFFAOYSA-N

CAS DataBase Reference

4187-87-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

RIDADR 

UN2810

WGK Germany 

3

RTECS 

DO5900000

HazardClass 

6.1

PackingGroup 

III

HS Code 

29062990

Toxicity

mouse,LD50,intraperitoneal,240mg/kg (240mg/kg),Farmaco, Edizione Scientifica. Vol. 8, Pg. 406, 1953.

MSDS

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

1-PHENYL-2-PROPYN-1-OL Usage And Synthesis

Chemical Properties

Clear yellow liquid

Synthesis

The general procedure for the synthesis of (±)-1-phenyl-2-propyn-1-ol from benzaldehyde and acetylene was as follows: magnesium (518 mg, 28.3 mmol) was placed in a pre-flame-dried, two-necked, round-bottomed flask fitted with a reflux condenser and cooled to room temperature under argon atmosphere. Subsequently, tetrahydrofuran (30 mL) and a small amount of iodine crystals were added. Next, a portion of the total volume of n-butyl chloride (2.23 mL, 28.3 mmol) was added dropwise and the mixture was refluxed until the Grignard reagent was generated. After removing the unreacted n-butyl chloride, the remaining n-butyl chloride was added. Stirring was continued at room temperature until all the magnesium was consumed. The reaction mixture was cooled to 0°C and acetylene gas was passed into it over a period of 15 minutes. Subsequently, benzaldehyde (1.0 g, 9.4 mmol) dissolved in tetrahydrofuran (20 mL) was added at 0°C and stirred for 6 hours. Upon completion of the reaction, the reaction was quenched with saturated ammonium chloride solution, diluted with water and extracted with ethyl acetate. The organic layers were combined, dried with anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (eluent 10% petroleum ether solution of ethyl acetate) to afford the target product (±)-1-phenyl-2-propyn-1-ol (1.08 g, 86% yield) as a pale yellow oil.

References

[1] Liebigs Annalen der Chemie, 1982, # 9, p. 1750 - 1752
[2] Organic and Biomolecular Chemistry, 2013, vol. 11, # 35, p. 5954 - 5962
[3] Patent: WO2015/193915, 2015, A1. Location in patent: Page/Page column 11
[4] Liebigs Annalen, 1995, # 7, p. 1353 - 1360
[5] Synthesis, 2004, # 9, p. 1381 - 1390

1-PHENYL-2-PROPYN-1-OL(4187-87-5)Related Product Information

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• 1,1,4,4-TETRAPHENYL-2-BUTYN-1,4-DIOL
• 1,1-DIPHENYL-2-PROPYN-1-OL
• 9-ETHYNYL-9-FLUORENOL
• (-)-1,6-BIS(2-CHLOROPHENYL)-1,6-DIPHENYL-2,4-HEXADIYNE-1,6-DIOL
• 1-PHENYL-2-PROPYN-1-OL
• (R)-1-PHENYL-2-PROPYN-1-OL
• 1-PHENYL-1-PROPYN-3-OL,3-PHENYL-2-PROPYN-1-OL,3-PHENYL-2-PROPYN-1-OL 98+%,2-phenyl-2-propyn-1-ol
• Propyne
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• 3-PHENYL-1-PROPYNE
• Butinoline
• (S)-1-PHENYL-2-PROPYN-1-OL
• (+)-1,6-BIS(2-CHLOROPHENYL)-1,6-DIPHENYL-2,4-HEXADIYNE-1,6-DIOL
• 1,1,1-TRIFLUORO-2-PHENYL-3-BUTYN-2-OL
• 2,4-DIPHENYL-3-BUTYN-2-OL