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| | 1-Phenyl-2-propyn-1-ol Basic information |
| | 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.) | | Fp | 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 | | InChI | 1S/C9H8O/c1-2-9(10)8-6-4-3-5-7-8/h1,3-7,9-10H | | InChIKey | UIGLAZDLBZDVBL-UHFFFAOYSA-N | | SMILES | OC(C#C)c1ccccc1 | | CAS DataBase Reference | 4187-87-5(CAS DataBase Reference) |
| 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 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 | | Toxicity | mouse,LD50,intraperitoneal,240mg/kg (240mg/kg),Farmaco, Edizione Scientifica. Vol. 8, Pg. 406, 1953. |
| | 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 Preparation Products And Raw materials |
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