(4-BROMOPHENOXY)-TERT-BUTYLDIMETHYLSILANE Chemical Properties

Boiling point:

137 °C25 mm Hg(lit.)

Density 

1.174 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.511(lit.)

Flash point:

53 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Chloroform, Ethyl Acetate, Methanol

form 

Liquid

Specific Gravity

1.175

color 

Colorless

Hydrolytic Sensitivity

4: no reaction with water under neutral conditions

InChI

InChI=1S/C12H19BrOSi/c1-12(2,3)15(4,5)14-11-8-6-10(13)7-9-11/h6-9H,1-5H3

InChIKey

DLGZGLKSNRKLSM-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

16-26-36-37/39-60-37-23

RIDADR 

UN 1993 3/PG 2

WGK Germany 

3

TSCA 

No

HazardClass 

3

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich

(4-BROMOPHENOXY)-TERT-BUTYLDIMETHYLSILANE Usage And Synthesis

Chemical Properties

Colourless Oil

Synthesis

Step 1a: 4-Bromophenol (10.0 g, 57.8 mmol) and tert-butyldimethylchlorosilane (TBSCl, 11.3 g, 75.14 mmol) were sequentially added to dry DMC (100 mL). Triethylamine (Et3N, 16.7 g, 115.6 mmol) was slowly added dropwise at room temperature, and the reaction mixture was continued to be stirred for 2 h after the dropwise addition. After completion of the reaction, the solvent was removed by distillation under reduced pressure. Petroleum ether (200 mL) was added to the residue, transferred to a partition funnel, and the organic layer was washed sequentially with water and saturated saline. The organic layer was dried with anhydrous sodium sulfate (Na2SO4), filtered and purified by a short silica gel column, and finally the solvent was evaporated under reduced pressure to give the target product (4-bromophenoxy)tert-butyldimethylsilane (compound 0101, 16.6 g, 100% yield) as a colorless oil.1H NMR (CDCl3) δ: 0.18 (s, 6H), 0.98 (s, 9H), and 2.71 (t, J = 6 Hz, 2H), 6.70-6.73 (m, 2H), 7.30-7.33 (m, 2H).

References

[1] Journal of Chemical Research, Miniprint, 1987, # 12, p. 3144 - 3177
[2] Bioorganic and medicinal chemistry, 2003, vol. 11, # 16, p. 3457 - 3474
[3] Tetrahedron Letters, 2004, vol. 45, # 33, p. 6357 - 6359
[4] Patent: US2009/76006, 2009, A1. Location in patent: Page/Page column 29; 34-35
[5] Patent: EP747704, 2003, B1. Location in patent: Page 11

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