| Identification | Back Directory | [Name]
1-ETHYNYL-3 5-DIMETHOXYBENZENE 98 | [CAS]
171290-52-1 | [Synonyms]
1-Ethylnyl-3,5-dimethoxybenzene
-ETHYNYL-3 5-DIMETHOXYBENZENE 98
Benzene, 1-ethynyl-3,5-diMethoxy-
1-ETHYNYL-3 5-DIMETHOXYBENZENE 98
1-Ethynyl-3,5-diMethoxybenzene 98% (CP) | [Molecular Formula]
C10H10O2 | [MDL Number]
MFCD03839985 | [MOL File]
171290-52-1.mol | [Molecular Weight]
162.185 |
| Chemical Properties | Back Directory | [Melting point ]
44-48 °C(lit.)
| [Boiling point ]
264.1±30.0℃ (760 Torr) | [density ]
1.06±0.1 g/cm3 (20 ºC 760 Torr) | [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [color ]
White to Orange to Green | [InChI]
InChI=1S/C10H10O2/c1-4-8-5-9(11-2)7-10(6-8)12-3/h1,5-7H,2-3H3 | [InChIKey]
HUSBBWQIJMRKLI-UHFFFAOYSA-N | [SMILES]
C1(C#C)=CC(OC)=CC(OC)=C1 |
| Hazard Information | Back Directory | [Description]
1-ethynyl-3,5-dimethoxybenzene is an organic reagent. Its benzene ring structure contains one acetylene group and two methoxy groups respectively, which are key structures for the synthesis of other heterocyclic compounds. | [Synthesis]
Under argon protection, 1-(2,2-dibromovinyl)-3,5-dimethoxybenzene (2.99 g, 9.28 mmol, 1 eq.) was dissolved in anhydrous tetrahydrofuran (50 mL) and stirred at -50 °C (dry ice/acetonitrile bath). Slowly n-butyllithium (24.0 mL, 1.6 M hexane solution, 38.4 mmol, 4.1 eq.) was added dropwise and the progress of the reaction was monitored by thin-layer chromatography (TLC) until the reaction was complete. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (40 mL) and subsequently extracted with dichloromethane (3 x 20 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give an orange-brown oil (1.61 g). Purification by fast column chromatography (eluent: pure pentane followed by 19:1 pentane:ether) afforded a colorless crystalline solid 3,5-dimethoxyphenylacetylene (1.22 g, 81% yield) with Rf = 0.24 (pentane) and a melting point of 205 °C. The NMR hydrogen spectrum (400 °F) of 3,5-dimethoxyphenylacetylene was obtained as follows. Its NMR hydrogen spectrum (400.1 MHz, CDCl3) data were as follows: δ 6.72 (d, J = 2.3 Hz, 2H, ArH), 6.50 (t, J = 2.3 Hz, 1H, ArH), 3.76 (s, 6H, OCH3), 3.15 (s, 1H, C≡CH). The NMR carbon spectrum (100.6 MHz, CDCl3) data are as follows: δ 160.6 (C), 123.4 (C), 110.0 (CH), 102.3 (CH), 83.7 (C), 76.9 (CH), 55.4 (CH3). | [References]
[1] Tetrahedron Letters, 2009, vol. 50, # 17, p. 1969 - 1972
[2] Chemistry Letters, 2008, vol. 37, # 2, p. 174 - 175
[3] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 273 - 279
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 6, p. 2386 - 2396
[5] Tetrahedron, 2017, vol. 73, # 33, p. 5023 - 5028 |
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