1,3,5-TRIETHYNYLBENZENE Chemical Properties

Melting point:

105-107°C

Boiling point:

272.3±35.0 °C(Predicted)

Density 

1.05±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 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 Information

Hazard Codes 

Xi

Risk Statements 

10-20/21-36/37/38-65-36

Safety Statements 

16-26-36/37/39-60-43-37-33-7

RIDADR 

1325

WGK Germany 

3

Hazard Note 

Irritant/Flammable

HazardClass 

4.1

PackingGroup 

III

HS Code 

29029090

MSDS

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1,3,5-TRIETHYNYLBENZENE Usage And Synthesis

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

1,3,5-TRIETHYNYLBENZENE(7567-63-7)Related Product Information

• 1,4-Diethynylbenzene
• TRIS-[11-PENTAKIS-(4'-ETHYLPHENYLETHYNYL)PHENOXYUNDECYL]TRIMESATE
• 11-[PENTAKIS-(4-PROPYLPHENYLETHYNYL)-PHENYLOXY]-UNDECAN-1-OL
• 1,3,5-TRIS(PHENYLETHYNYL)BENZENE
• TRIS-[11-PENTAKIS-(4'-PROPYLPHENYLETHYNYL)PHENOXYUNDECYL]TRIMESATE
• 1,3,5-TRIETHYNYLBENZENE