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89031-84-5

89031-84-5 Structure

89031-84-5 Structure
IdentificationBack Directory
[Name]

(3-BROMOPROPOXY)-TERT-BUTYLDIMETHYLSILANE
[CAS]

89031-84-5
[Synonyms]

89031-84-5
(3-Bromopropoxy)-tert-butyL
cyclohex-1-ene-1-carbaldehyde
3-BROMOPROPOXY-T-BUTYLDIMETHYLSILANE
3-BroMoethoxy-tert-butyl diMethylsilane
(3-BroMopropoxy)-t-buyl-1-diMethylsilane
(3-BROMOPROPOXY)-TERT-BUTYLDIMETHYLSILANE
1-Bromo-3-(tert-butyldimethylsiloxy)propane
(3-Bromopropoxy)-tert-butyldimethylsilane 97%
Silane,(3-bromopropoxy)(1,1-dimethylethyl)dimethyl-
93-Bromopropoxy)-tert-butyldimethylsilane(Na2CO3 stabiliszer)975
(3-BroMopropoxy)-tert-butyldiMethylsilane, 97%, stabilized over sodiuM carbonate
[Molecular Formula]

C9H21BrOSi
[MDL Number]

MFCD00216589
[MOL File]

89031-84-5.mol
[Molecular Weight]

253.25
Chemical PropertiesBack Directory
[Boiling point ]

182 °C(lit.)
[density ]

1.093 g/mL at 25 °C(lit.)
[refractive index ]

n20/D 1.451(lit.)
[Fp ]

185 °F
[storage temp. ]

2-8°C
[solubility ]

Chloroform (Sparingly)
[form ]

Oil
[color ]

Colourless
[InChI]

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

QGMROEZDWJTIDW-UHFFFAOYSA-N
[SMILES]

CC(C)(C)[Si](C)(C)OCCCBr
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P264-P271-P280-P302+P352-P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26
[WGK Germany ]

3
[TSCA ]

No
[HS Code ]

29319090
[Storage Class]

10 - Combustible liquids
[Hazard Classifications]

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Hazard InformationBack Directory
[Uses]

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

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

tert-Butyldimethylsilyl chloride

18162-48-6

3-Bromo-1-propanol

627-18-9

(3-BROMOPROPOXY)-TERT-BUTYLDIMETHYLSILANE

89031-84-5

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
Spectrum DetailBack Directory
[Spectrum Detail]

(3-BROMOPROPOXY)-TERT-BUTYLDIMETHYLSILANE(89031-84-5)1HNMR
(3-BROMOPROPOXY)-TERT-BUTYLDIMETHYLSILANE(89031-84-5)IR
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