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Sigma-Aldrich

(3-Bromopropoxy)-tert-butyldimethylsilane

97%

Synonym(s):

(3-Bromopropoxy)(1,1-dimethylethyl)dimethylsilane, 1-((tert-Butyldimethylsilyl)oxy)-3-bromopropane, 1-Bromo-3-(tert-butyldimethylsiloxy)propane, 1-Bromo-3-[(tert-butyldimethylsilanyl)oxy]propane, 1-Bromo-3-[(tert-butyldimethylsilyl)oxy]propane, 3-((tert-Butyldimethylsilyl)oxy)-1-bromopropane

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About This Item

Linear Formula:
Br(CH2)3OSi(CH3)2C(CH3)3
CAS Number:
89031-84-5
Molecular Weight:
253.25
MDL number:
MFCD00216589
UNSPSC Code:
12352100
PubChem Substance ID:
24866833
NACRES:
NA.22

Assay

97%

form

liquid

contains

sodium carbonate as stabilizer

refractive index

n20/D 1.451 (lit.)

bp

182 °C (lit.)

density

1.093 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)(C)[Si](C)(C)OCCCBr

InChI

1S/C9H21BrOSi/c1-9(2,3)12(4,5)11-8-6-7-10/h6-8H2,1-5H3

InChI key

QGMROEZDWJTIDW-UHFFFAOYSA-N

General description

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

Application

(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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

185.0 °F - closed cup

Flash Point(C)

85 °C - closed cup

Certificates of Analysis (COA)

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Synthesis of O-(3-[18F] Fluoropropyl)-L-tyrosine (L-[18F] FPT) and its biological evaluation in 9L tumor bearing rat.
Moon BS, et al.
Bull. Korean Chem. Soc., 26(1), 91-96 (2005)
Ramani R Ranatunge et al.
Journal of medicinal chemistry, 47(9), 2180-2193 (2004-04-16)
The synthesis of a series of novel pyrazoles containing a nitrate (ONO(2)) moiety as a nitric oxide (NO)-donor functionality is reported. Their COX-1 and COX-2 inhibitory activities in human whole blood are profiled. Our data demonstrate that pyrazole ring substituents
A concise total synthesis of (+/-)-vigulariol.
J Stephen Clark et al.
Angewandte Chemie (International ed. in English), 46(3), 437-440 (2006-12-06)
Han-Cheng Zhang et al.
Bioorganic & medicinal chemistry letters, 14(12), 3245-3250 (2004-05-20)
A novel series of acyclic 3-(7-azaindolyl)-4-(aryl/heteroaryl)maleimides was synthesized and evaluated for activity against GSK-3beta and selectivity versus PKC-betaII, as well as a broad panel of protein kinases. Compounds 14 and 17c potently inhibited GSK-3beta (IC(50)=7 and 26 nM, respectively) and
Synthesis, radioiodination and in vivo screening of novel potent iodinated and fluorinated radiotracers as melanoma imaging and therapeutic probes.
Maisonial A, et al.
European Journal of Organic Chemistry, 63, 840-853 (2013)
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