(3-BROMOPROPOXY)-TERT-BUTYLDIMETHYLSILANE Chemical Properties

Boiling point:

182 °C(lit.)

Density 

1.093 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.451(lit.)

Flash point:

185 °F

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly)

form 

Oil

color 

Colourless

InChIKey

QGMROEZDWJTIDW-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

TSCA 

No

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich

(3-BROMOPROPOXY)-TERT-BUTYLDIMETHYLSILANE Usage And Synthesis

Uses

The propanol functionality of this versatile reagent can be introduced to many pharmaceuticals.1,2,3,4

Uses

(3-Bromopropoxy)-tert-butyldimethylsilane may be used to introduce propanol functionality to many pharmaceuticals.
It may be used as an alkylating agent in the synthesis of the following:

• N-[2-[N-[3-(tert-butyldimethylsilyloxy)propyl]-N-ethylamino]ethyl]phthalimide
• O-(3-tert-butyldimethylsilyloxypropyl)-N-(tert-butoxycarbonyl)-L-tyrosine methyl ester
• tert-butyldimethyl-[3-(3-methyl-2-nitrophenoxy)propoxy]silane

Uses

(3-Bromopropoxy)-tert-butyldimethylsilane is a reagent in the preparation of piperidinylcarbonyl sulfamates as a novel class of antihyperlipidemic agents with LDL-receptor up-regulation via the adaptor protein autosomal recessive hypercholesterolemia.

General Description

(3-Bromopropoxy)-tert-butyldimethylsilane is a bromo silyl ether.

Synthesis

Example C: Synthesis of 3-(3-(2,5-dioxo-4-(3,4,5-trimethoxyphenyl)-2,5-dihydro-1H-pyrrol-3-yl)-1H-indol-1-yl)-2-amino-4-methylpentanoic acid propyl ester of 3-bromopropoxy-tert-butyl dimethylsilane. (3-Bromopropoxy)tert-butyldimethylsilane was prepared using the method modified by Galka et al. (J. Lab. Comp. Rad. 2005, 48(11): 797-809). The procedure was as follows: a mixture of 3-bromo-1-propanol (39.1 mmol, 5.43 g), tert-butyldimethylchlorosilane (43.2 mmol, 6.47 g) and imidazole (46.7 mmol, 3.20 g) was stirred and reacted for 3 h at room temperature under inert gas protection. After completion of the reaction, the reaction was quenched with water and the reaction mixture was extracted with diethyl ether. The organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated. Purification by column chromatography (with petroleum ether as eluent) afforded the target product (3-bromopropoxy)tert-butyldimethylsilane (36.4 mmol, 93% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 3.73 (t, 3J = 5.7 Hz, 2H, CH2O), 3.51 (t, 3J = 6.4 Hz, 2H, CH2Br), 2.02 (q, 3J = 5.7 Hz, 3J = 6.4 Hz, 2H, CH2CH2CH2), 0.89 (s, 9H, C( CH3)3), 0.06 (s, 6H, 2×CH3).

References

[1] Heterocycles, 2004, vol. 62, p. 423 - 436
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 14, p. 5080 - 5095
[3] Tetrahedron Letters, 2012, vol. 53, # 36, p. 4805 - 4808
[4] Journal of the American Chemical Society, 2012, vol. 134, # 43, p. 18101 - 18108
[5] Journal of Labelled Compounds and Radiopharmaceuticals, 2005, vol. 48, # 11, p. 797 - 809

(3-BROMOPROPOXY)-TERT-BUTYLDIMETHYLSILANE(89031-84-5)Related Product Information

• T-BUTYLDIMETHYLSILANE
• TRANS-3-BROMO-5-TERT-BUTYL-DIMETHYLSILYLOXY-2-PENTEN-1-OL
• (3-BROMOPROPOXY)-TERT-BUTYLDIMETHYLSILANE