| Identification | Back Directory | [Name]
(4-BROMOPHENOXY)-TERT-BUTYLDIMETHYLSILANE | [CAS]
67963-68-2 | [Synonyms]
AKOS 228-12
P-BROMOPHENOXY(T-BUTYL)DIMETHYLSILANE
4-Bromophenoxy t-Butyl Dimethylsilane
(4-BROMOPHENOXY)-TERT-BUTYLDIMETHYLSILANE
4-BroMophenyl tert-ButyldiMethylsilyl Ether
1-Bromo-4-(tert-butyldimethylsiloxy)benzene
1-BroMo-4-[[(1,1-diMethylethyl)diMethylsilyl]oxy]benzene
Benzene, 1-bromo-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]- | [Molecular Formula]
C12H19BrOSi | [MDL Number]
MFCD00239382 | [MOL File]
67963-68-2.mol | [Molecular Weight]
287.27 |
| Chemical Properties | Back Directory | [Boiling point ]
137 °C25 mm Hg(lit.)
| [density ]
1.174 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.511(lit.)
| [Fp ]
53 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Chloroform, Ethyl Acetate, Methanol | [form ]
Liquid | [color ]
Colorless | [Specific Gravity]
1.175 | [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 |
| Hazard Information | Back Directory | [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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