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Home > Encyclopedia > 1,3,5-TRIETHYNYLBENZENE

1,3,5-TRIETHYNYLBENZENE

1,3,5-TRIETHYNYLBENZENE structure

1,3,5-TRIETHYNYLBENZENE 

structure
  • CAS No:

    7567-63-7

  • Formula:

    C12H6

  • Chemical Name:

    1,3,5-TRIETHYNYLBENZENE

  • Synonyms:

    1,3,5-TRIETHYNYLBENZENE;Benzene, 1,3,5-triethynyl- (8CI, 9CI);NISTC7567637;1,3,5-Triethynylbenzene 97%;3,5,-Triethynylbenzene;1,3,5-triethynylbenzene7567-63-7;1,3,5-Triethynylbenzene 98+%;C:C&B46

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

Light yellow to Brown solid

1,3,5-TRIETHYNYLBENZENE Basic Attributes

150.18

150.046951

DTXSID00226581

Light yellow to Brown

29029090

Characteristics

0

2.7

1.05±0.1 g/cm3(Predicted)

105-107°C

272.3±35.0 °C(Predicted)

107.6±20.1 °C

1.588

Soluble in methanol. Insoluble in water.

under inert gas (nitrogen or Argon) at 2-8°C

Safety Information

III

4.1

1325

3

Xi

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

Xi

Irritant/Flammable

P264, P280, P305+P351+P338, P33, P313

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

1325

1,3,5-TRIETHYNYLBENZENE Use and Manufacturing

Methods of Manufacturing

(9) A (1 g, 2.73 mmol) and K2CO3 (1.24 g, 8.99 mmol) were dissolved in 100 mL CHCl3/MeOH 3:2 and stirred at rt for 24 h. The solvent was removed on a rotary evaporator and the off-white solid was purified by silica gel column chromatography using dichloromethane/hexane 1:4 to give the product. Isolated yield: 350 mg. 1H NMR (CDCl3, 400 MHz): (ppm) 7.57 (s, 3H, H1), 3.11 (s, 3H, H2). 13C{1H} NMR (CDCl3, 100 MHz): (ppm) 136.12, 132.48, 123.38, 123.01, 83.51, 82.10, 70.59, 79.19.General procedure: The procedure was modified following the Sonogashira coupling protocol. 1, 3, 5-Tribromobenzene (31.5 g, 100 mmol) was dissolved in dry triethylamine (250 mL) under an atmosphere of nitrogen. Copper(I) iodide (191 mg, 1.0 mmol), dichlorobis(dibenzonitrile)palladium(II) (192 mg, 0.5 mmol) were added to the stirred solution. 2.2.2 1, 3, 5-Triethynylbenzene 2 [15]A solution of 3 (6.54 g, 19.62 mmol) in toluene (100 mL) was heated up to boiling.Powdered potassium hydroxide (3.30 g, 58.86 mmol) was added and the mixture refluxed for 5 h. After cooling down to room temperature, diethyl ether (50 mL) was added. The organic phase was washed with water (2 * 100 mL)

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.

Computed Properties

Molecular Weight:150.18
XLogP3:2.7
Rotatable Bond Count:3
Exact Mass:150.0469501914
Monoisotopic Mass:150.0469501914
Heavy Atom Count:12
Complexity:230
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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