(4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE Chemical Properties

Melting point:

61-63 °C(lit.)

Boiling point:

60-80°C/0.2mmHg

Density 

1,192 g/cm³

storage temp. 

2-8°C

form 

Powder

color 

White to yellow

Specific Gravity

1.192

Hydrolytic Sensitivity

1: no significant reaction with aqueous systems

InChI

InChI=1S/C11H13BrSi/c1-13(2,3)9-8-10-4-6-11(12)7-5-10/h4-7H,1-3H3

InChIKey

RNMSGCJGNJYDNS-UHFFFAOYSA-N

SMILES

C1(Br)=CC=C(C#C[Si](C)(C)C)C=C1

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

TSCA 

No

HS Code 

2931.90.6000

MSDS

• Language:English Provider:SigmaAldrich

(4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE Usage And Synthesis

Uses

(4-Bromophenylethynyl)trimethylsilane may be used to synthesize:

• 1-bromo-4-ethynylbenzene
• 4-(4-bromophenyl)-3-butyn-2-one
• 4-ethynyl-4′-tert-butylbiphenyl
• 1,4-bis[2-(4-bromophenyl)ethynyl]-2,5-dihexylbenzene

General Description

(4-Bromophenylethynyl)trimethylsilane can be synthesized by the palladium catalyzed reaction between 4-bromo-1-iodobenzene and trimethylsilylacetylene. It undergoes Buchwald-Hartwig coupling with para-substituted diphenylamines.

Synthesis

In a two-necked round-bottomed flask (RBF) equipped with a magnetic stirrer, triethylamine (TEA, 200 mL) was added and 1-bromo-4-iodobenzene (24.00 g, 84.83 mmol) was added at room temperature and protected by nitrogen. After stirring the mixture for 5 min, ethynyltrimethylsilane (13.19 mL, 93.31 mmol), dichlorobis(triphenylphosphine)palladium(II) (Pd(PPh3)2Cl2, 2.98 g, 4.24 mmol), and cuprous iodide (CuI, 1.62 g, 8.48 mmol) were added sequentially. The reaction mixture was continued to be stirred at the same temperature for 30 min. Subsequently, the excess TEA was removed by vacuum evaporation and the pH was adjusted to 1 by adding 1 N hydrochloric acid. extraction was carried out with ethyl acetate (EtOAc) and water, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate (MgSO4). After evaporation of the solvent, the residue was purified by column chromatography (eluent: hexane) to afford the target compound (4-bromophenyl ethynyl)trimethylsilane (21.00 g, 98% yield) as a white solid.1H NMR (CDCl3, 500 MHz): δ 7.19-7.06 (4H, m, ArH), 0.00 (9H, s, Si(CH3)3); 13C NMR (CDCl3, 125 MHz): δ 133.5, 131.6, 122.8, 122.3, 104.0, 95.7, 0.00.

References

[1] Journal of Organic Chemistry, 2015, vol. 80, # 8, p. 4097 - 4107
[2] Dalton Transactions, 2013, vol. 42, # 2, p. 338 - 341
[3] Organometallics, 2014, vol. 33, # 18, p. 4947 - 4963
[4] Synlett, 1999, # 6, p. 750 - 752
[5] Tetrahedron Letters, 2005, vol. 46, # 1, p. 27 - 30

(4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE(16116-78-2)Related Product Information

• (4-ethenylphenyl)Methyl-triMethylsilane
• TERT-BUTYL(4-IODOBUTOXY)DIMETHYLSILANE
• METHYLSILANE
• (3-BROMOPHENYLETHYNYL)TRIMETHYLSILANE
• (2-BROMOPHENYLETHYNYL)TRIMETHYLSILANE
• (2-BROMOPHENYLETHYNYL)TRIMETHYLSILANE, 9 8%
• 4-Bromophenylacetylene
• PHENYLETHYNYLDIMETHYLSILANE
• (4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE
• 1-PHENYL-2-(TRIMETHYLSILYL)ACETYLENE