177329-71-4

Basic information

• Product Name: 2-(t-Butyldimethylsilyloxy)-4-bromoanisole
• Synonyms: 2-(t-Butyldimethylsilyloxy)-4-bromoanisole;(5-Bromo-2-methoxyphenoxy)(tert-butyl)dimethylsilane
• CAS NO: 177329-71-4
• Molecular Formula: C₁₃H₂₁BrO₂Si
• Molecular Weight: 317.29414
• Mol File: 177329-71-4.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(t-Butyldimethylsilyloxy)-4-bromoanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(t-Butyldimethylsilyloxy)-4-bromoanisole(177329-71-4)
• EPA Substance Registry System: 2-(t-Butyldimethylsilyloxy)-4-bromoanisole(177329-71-4)

Safety Data

• Hazardous Substances Data: 177329-71-4(Hazardous Substances Data)

Usage

General Description

2-(t-Butyldimethylsilyloxy)-4-bromoanisole, also known as TBDMSCl, is a chemical compound with the molecular formula C15H25BrO2Si. It is a derivative of anisole, a phenyl ether, and contains a bromine atom and a t-butyldimethylsilyloxy group. TBDMSCl is commonly used as a protecting group in organic synthesis to temporarily protect hydroxyl groups, particularly in the synthesis of complex organic molecules. It is a colorless liquid with a boiling point of 160-165°C at 760 mmHg and is used in various chemical reactions to facilitate specific transformations without impacting other functional groups present in the molecule.

Upstream product

• 37942-01-1 5-bromo-2-methoxyphenol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 25016-01-7 5-bromo-2-methoxybenzaldehyde 
• 7368-78-7 4-bromoguaiacol 
• 90-05-1 2-methoxy-phenol 

Downstream Products

• 97315-21-4 (R)-2-(3-tert-butyldimethylsilyloxy-4-methoxy)phenyl-1-(3,4,5-trimethoxyphenyl)ethanol 
• 185698-54-8 2-[3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl]-1-(3,4,5-trimethoxyphenyl)ethyne 
• 612481-30-8 (2aS,4R,4aR,7aR,7bR)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-5-methylene-4-vinyl-decahydro-indeno[7,1-bc]furan-2-ol 
• 117048-62-1 combrestatin A₄ 
• 121042-95-3 (Z)-5-(3-tert-butyldimethylsilyloxy-4-methoxystyryl)-1,2,3-trimethoxybenzene 
• 185698-55-9 2-(3-hydroxy-4-methoxyphenyl)-1-(3',4',5'-trimethoxyphenyl)ethyne 
• 82855-09-2 (-)-combretastatin 
• 143702-43-6 5-[1-Hydroxy-3-(3,4,5-trimethoxy-phenyl)-propyl]-2-methoxy-phenol 
• 143702-44-7 Acetic acid 4-[1-hydroxy-3-(3,4,5-trimethoxy-phenyl)-propyl]-1-methoxy-6-oxo-cyclohexa-2,4-dienyl ester 
• 1189545-68-3 5-{[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-hydroxy-methyl}-2-chloro-benzenesulfonamide 
• 1293408-37-3 C₂₃H₃₀O₇Si 
• 1293408-38-4 C₂₃H₃₀O₇Si 
• 1293408-39-5 C₂₂H₂₈O₆Si 
• 1293408-40-8 C₂₄H₃₄O₇Si 

Relevant articles and documents

The synthesis and evaluation of temperature sensitive tubulin toxins

The synthesis of several potent inhibitors of tubulin polymerization that exert their activities through interaction at the colchicine binding site is described. These agents were evaluated for their abilities to inhibit the polymerization of tubulin and the growth of neoplastic cell cultures. Additionally, the inhibition of tubulin polymerization activity of these agents was assessed over a temperature range of 30-45°C to ascertain the effect of temperature on this activity. Several of the compounds possess significant inhibition of tubulin polymerization activity, and select compounds exhibit this activity in a temperature dependent manner.

Facile synthesis of 1,2-dione-containing abietane analogues for the generation of human carboxylesterase inhibitors

Recently, a series of selective human carboxylesterase inhibitors have been identified based upon the tanshinones, with biologically active molecules containing a 1,2-dione group as part of a naphthoquinone core. Unfortunately, the synthesis of such compounds is complex. Here we describe a novel method for the generation of 1,2-dione containing diterpenoids using a unified approach, by which boronic acids are joined to vinyl bromo-cyclohexene derivatives via Suzuki coupling, followed by electrocyclization and oxidation to the o-phenanthroquinones. This has allowed the construction of a panel of miltirone analogues containing an array of substituents (methyl, isopropyl, fluorine, methoxy) which have been used to develop preliminary SAR with the two human carboxylesterase isoforms. As a consequence, we have synthesized highly potent inhibitors of these enzymes (Ki 15 nM), that maintain the core tanshinone scaffold. Hence, we have developed a facile and reproducible method for the synthesis of abietane analogues that have resulted in a panel of miltirone derivatives that will be useful tool compounds to assess carboxylesterase biology.

Constructing novel dihydrofuran and dihydroisoxazole analogues of isocombretastatin-4 as tubulin polymerization inhibitors through [3+2] reactions

[3+2] reactions play a key role in constructing various pharmaceutical moleculars. In this study, using Mn(OAc)3 mediated and 1,3-dipolar [3+2] cyclization reactions, 38 novel dihydrofuran and dihydroisoxazole analogues of isoCA-4 were synthesized as inhibitors of tubulin polymerization. Among them, compound 6g was found to be the most potent cytotoxic agents against PC-3 cells with IC50 value of 0.47 μM, and compound 5p exhibted highest activity on HeLa cells with IC50 vaule of 2.32 μM. Tubulin polymerization assay revealed that 6g was a dose-dependent and effective inhibitor of tubulin assembly. Immunohistochemistry studies and cell cycle distribution analysis indicated that 6g severely disrupted microtubule network and significantly arrested most cells in the G2/M phase of the cell cycle in PC-3 cells. In addition, molecular docking studies showed that two chiral isomers of 6g can bind efficiently and similarly at colchicine binding site of tubulin.