| Identification | More | [Name]
1,3,5-TRIETHYNYLBENZENE | [CAS]
7567-63-7 | [Synonyms]
1,3,5-TRIETHYNYLBENZENE
Benzene, 1,3,5-triethynyl-(8CI, 9CI)
NISTC7567637 | [Molecular Formula]
C12H6 | [MDL Number]
MFCD00068621 | [Molecular Weight]
150.18 | [MOL File]
7567-63-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
105-107°C | [Boiling point ]
272.3±35.0 °C(Predicted) | [density ]
1.05±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
powder to crystal | [color ]
Light yellow to Brown | [Water Solubility ]
Soluble in methanol. Insoluble in water. | [InChI]
InChI=1S/C12H6/c1-4-10-7-11(5-2)9-12(6-3)8-10/h1-3,7-9H | [InChIKey]
ZDRMMTYSQSIGRY-UHFFFAOYSA-N | [SMILES]
C1(C#C)=CC(C#C)=CC(C#C)=C1 | [CAS DataBase Reference]
7567-63-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R10:Flammable.
R20/21:Harmful by inhalation and in contact with skin .
R36/37/38:Irritating to eyes, respiratory system and skin .
R65:Harmful: May cause lung damage if swallowed. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
1325 | [WGK Germany ]
3 | [Hazard Note ]
Irritant/Flammable | [HazardClass ]
4.1 | [PackingGroup ]
III | [HS Code ]
29029090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow to Brown solid | [Uses]
1,3,5-Triethynylbenzene is used as the carbon precursor for graphene synthesis on rhodium. It is also used as a connecting unit for various transition metal building blocks. | [Synthesis]
Procedure for the synthesis of 1,3,5-triethynylbenzene: To a flame-dried flask under argon protection was added 1,3,5-tris((trimethylsilyl)ethynyl)benzene (2.39 mmol, 1 eq.), cesium carbonate (4.78 mmol, 2 eq.) and methanol (10 mL). The reaction mixture was stirred for 16 hours. Upon completion of the reaction, the solution changed from opaque to translucent. Methanol was removed by distillation under reduced pressure and the residual solid was partitioned between water and dichloromethane. The aqueous layer was extracted with dichloromethane (3 x 20 mL). The combined organic layers were washed sequentially with aqueous ammonium chloride (1.0 M, 2 × 20 mL), water (2 × 20 mL) and brine (2 × 20 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the off-white soft crystal-like product 1,3,5-triethynylbenzene (2.09 mmol) in 87% yield with a melting point of 101-103 °C. The product was obtained by 1H NMR. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3) δ 7.57 (s, 3H), 3.12 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 135.6, 122.8, 81.6, 78.7; MS (CI+) m/z 151 [M]+. | [References]
[1] Journal of Materials Chemistry, 2008, vol. 18, # 9, p. 1037 - 1045
[2] Tetrahedron Asymmetry, 2007, vol. 18, # 23, p. 2820 - 2827
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 21, p. 5106 - 5109
[4] Angewandte Chemie - International Edition, 2016, vol. 55, # 24, p. 6858 - 6863
[5] Angew. Chem., 2016, vol. 24, p. 6972 - 6977,6 |
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