83067-20-3

Basic information

• Product Name: 5-(TERT-BUTYLDIMETHYLSILYLOXY)-1-PENTANOL
• Synonyms: 5-(TERT-BUTYLDIMETHYLSILYLOXY)-1-PENTANOL;5-(tert-Butyldimethylsiloxy)-1-pentanol;5-[Dimethyl(tert-butyl)silyloxy]-1-pentanol;5-[(tert-butyldiMethylsilyl)oxy]pentan-1-ol;1-Pentanol,5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-;5-(tert-Butyldimethylsilyloxy)-1-pentanol 90%
• CAS NO: 83067-20-3
• Molecular Formula: C₁₁H₂₆O₂Si
• Molecular Weight: 218.41
• Product Categories: Alcohols;C9 to C30;Oxygen Compounds
• Mol File: 83067-20-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 140 °C6 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.885 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00367mmHg at 25°C
• Refractive Index: n20/D 1.442(lit.)
• PKA: 15.15±0.10(Predicted)
• CAS DataBase Reference: 5-(TERT-BUTYLDIMETHYLSILYLOXY)-1-PENTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(TERT-BUTYLDIMETHYLSILYLOXY)-1-PENTANOL(83067-20-3)
• EPA Substance Registry System: 5-(TERT-BUTYLDIMETHYLSILYLOXY)-1-PENTANOL(83067-20-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 83067-20-3(Hazardous Substances Data)

Usage

Uses

5-(tert-Butyldimethylsilyloxy)-1-pentanol is used as a reagent in the synthesis of chroman-4-one and chromone-based sirtuin 2 inhibitors with antiproliferative properties in cancer cells.

General Description

5-(tert-Butyldimethylsilyloxy)-1-pentanol participates in the synthesis of well-defined mono- and ditelechelic polyphosphazenes.

InChI:InChI=1/C11H26O2Si/c1-11(2,3)14(4,5)13-10-8-6-7-9-12/h12H,6-10H2,1-5H3

Upstream product

• 121671-67-8 1-(tert-butyldiphenylsilanyloxy)-5-(tert-butyldimethylsilanyloxy)pentane 
• 410087-91-1 (1,1-dimethylethyl)dimethyl[5-(3-methyl-2-butenyloxy)pentyl]oxy silane 
• 126889-45-0 1-(tert-Butyl-dimethyl-silanyloxy)-5-(diethyl-isopropyl-silanyloxy)-pentane 

Downstream Products

• 125878-24-2 5-Benzyloxy-pentanoic acid 5-(tert-butyl-dimethyl-silanyloxy)-pentyl ester 
• 1638136-69-2 (E)-N-((E)-3-bromo-2-methylbut-2-en-1-yl)-N'-(5-((tertbutyldimethylsilyl)oxy)pentylidene)-4-methylbenzenesulfonohydrazide 
• 1638136-68-1 (E)-N-((E)-3-bromo-2-methylallyl)-N'-(5-((tertbutyldimethylsilyl)oxy)pentylidene)-4-methylbenzenesulfonohydrazide 
• 1616561-89-7 2-ethyl-2-(3-phenylpropoxy)tetrahydro-2H-pyran 
• 1616561-78-4 5-(3-phenylpropoxy)hept-6-en-1-ol 
• 1616562-08-3 tert-butyldimethyl((5-(3-phenylpropoxy)hept-6-en-1-yl)oxy)silane 
• 92362-23-7 1-hydroxydec-9-en-5-one 
• 230285-14-0 1-phenyl-1-(2-tetrahydropyranyloxy)-5-pentanol 
• 1206146-95-3 5-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-pentan-1-ol 

Relevant articles and documents

Deprotection of a silyl group with mesoporous silica

The triethylsilyl (TES) group of silyl ethers of several types is selectively and easily removed in the presence of a t-butyldimethylsilyl (TBDMS) group with a mesoporous silica MCM-41/MeOH heterogeneous system. Comparison of the efficiency was carried out among several solvents, and among such promoters as common zeolites and ion-exchange resins. Furthermore, FSM-16, another mesoporous silica, was examined for the possibility of recycling by re-calcination at 400°C after the reaction.

The prenyl group: A versatile hydroxy protecting group, removable chemoselectively under mild conditions

Iodine in dichloromethane (in the presence of 3? molecular sieves for acid-sensitive substrates) and 2,3-dichloro-5,6-dicyanoquinone (DDQ) in dichloromethane-water (9:1) are mild and efficient methods to cleave prenyl ethers. These reaction conditions are compatible with the presence of other protecting groups such as acetals, acetates, allyl, benzyl and TBDPS groups. Exposure of aryl prenyl ethers to iodine led to the formation of 3-iodo-2,2-dimethylchroman derivatives in acceptable yields via a tandem Friedel-Crafts/iodocyclization reactions. Facile one-step transformation of two iodinated dimethylchroman derivatives allowed the synthesis of natural flavanoids among them: zanthoxylol, an anti-sickling agent.

Selective acceleration for deprotection of benzyl ethers with ti-HMS

Ti-HMS, a Ti-loaded hexagonal mesoporous silica, was found to accelerate deprotection of benzyl ethers under hydrogenolytic conditions with palladium catalyst. Such acid-sensitive functional groups as silyl ether and acetal moieties in the molecule were little affected by Ti-HMS, which possesses Lewis acid sites due to Ti-atom.