| Identification | More | [Name]
1-Butyl-4-eth-1-ynylbenzene | [CAS]
79887-09-5 | [Synonyms]
1-BUTYL-4-ETH-1-YNYLBENZENE
1-BUTYL-4-ETHYNYLBENZENE
4-BUTYLPHENYLACETYLENE
BENZENE, 1-BUTYL-4-ETHYNYL-
BUTTPARK 145\20-77
(P-BUTYLPHENYL)ACETYLENE | [EINECS(EC#)]
628-381-4 | [Molecular Formula]
C12H14 | [MDL Number]
MFCD00173885 | [Molecular Weight]
158.24 | [MOL File]
79887-09-5.mol |
| Chemical Properties | Back Directory | [Boiling point ]
70-71°C 3mm | [density ]
0.906 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.527(lit.)
| [Fp ]
215 °F
| [storage temp. ]
Inert atmosphere,2-8°C | [form ]
clear liquid | [color ]
Colorless to Light orange to Yellow | [Specific Gravity]
0.93 | [Usage]
Intermediates of Liquid Crystals | [CAS DataBase Reference]
79887-09-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29029090 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow liquid | [Uses]
4-Butylphenylacetylene is a useful research chemical, an intermediates of Liquid Crystals. | [Synthesis]
General steps:
1. Under argon protection, Pd(OAc)? (13.5 mg, 0.06 mmol), PPh? (31.5 mg, 0.12 mmol), CuI (5.7 mg, 0.03 mmol) and 1-bromo-4-butylbenzene (639 mg, 3.00 mmol) were dissolved in triethylamine (1 mL). A solution of trimethylmethylsilylacetylene (324 mg, 3.30 mmol) was subsequently added.
2. The reaction mixture was stirred at 80 °C for 4 h. Upon completion of the reaction, it was acidified with 1N HCl aqueous solution.
3. Deionized water and EtOAc were added, partitioned and the organic layer was collected. The aqueous layer was extracted with EtOAc and the organic layers were combined.
4. The organic layer was washed with saturated brine, dried over anhydrous MgSO?, filtered and concentrated under reduced pressure.
5. The crude product was purified by silica gel column chromatography with the eluent of petroleum ether/EtOAc (100:1, v/v, Rf = 0.43) to afford 1-(4-butylphenyl)-2-trimethylsilylacetylene (S8) as a light yellow oil (550 mg, 2.40 mmol, 80% yield).
6. S8 (550 mg, 2.40 mmol) and K?CO? (495 mg, 3.58 mmol) were suspended in MeOH (12 mL) and stirred at room temperature for 4 hours.
7. The reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure.
8. Deionized water and EtOAc were added, partitioned and the organic layer was collected. The aqueous layer was extracted with EtOAc and the organic layers were combined.
9. The organic layer was washed with saturated brine, dried over anhydrous MgSO?, filtered and concentrated under reduced pressure.
10. The crude product was purified by silica gel column chromatography with the eluent petroleum ether/EtOAc (50:1, v/v, Rf = 0.50) to afford 1-butyl-4-ethynylbenzene (S9) as a light yellow oil (340 mg, 2.15 mmol, 90% yield).
11. Under argon protection, Pd(OAc)? (8.8 mg, 0.039 mmol), PPh? (20.5 mg, 0.078 mmol), CuI (3.7 mg, 0.020 mmol) and S9 (340 mg, 2.15 mmol) were dissolved in triethylamine (1 mL).
12. The reaction mixture was stirred at 80 °C for 4 h. Upon completion of the reaction, it was acidified with 1N HCl aqueous solution.
13. The reaction mixture was treated according to the post-synthesis treatment of S8, and the crude product was purified by silica gel column chromatography with the eluent of petroleum ether/EtOAc (50:1, v/v, Rf = 0.30) to afford 1-butyl-4-phenylethynyl (4c) as a yellow solid (340 mg, 1.17 mmol, 60% yield). | [References]
[1] Bulletin of the Chemical Society of Japan, 2018, vol. 91, # 7, p. 1069 - 1074
[2] Journal of Medicinal Chemistry, 1991, vol. 34, # 4, p. 1440 - 1446 |
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