118736-04-2

Basic information

• Product Name: tert-Butyl[4-(dimethoxymethyl)phenoxy]dimethylsilane
• Synonyms: tert-Butyl[4-(dimethoxymethyl)phenoxy]dimethylsilane;1-(tert-Butyldimethylsilyloxy)-4-(dimethoxymethyl)benzene 4-(tert-Butyldimethylsilyloxy)benzaldehyde Dimethyl Acetal;tert-Butyl[4-(dimethoxymethyl)phenoxy]dimethylsilane
• CAS NO: 118736-04-2
• Molecular Formula: C₁₅H₂₆O₃Si
• Molecular Weight: 282.45064
• Mol File: 118736-04-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 287.6°C at 760 mmHg
• Flash Point: 106.7°C
• Appearance: /
• Density: 0.958g/cm³
• Vapor Pressure: 0.00425mmHg at 25°C
• Refractive Index: 1.4810-1.4850
• CAS DataBase Reference: tert-Butyl[4-(dimethoxymethyl)phenoxy]dimethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl[4-(dimethoxymethyl)phenoxy]dimethylsilane(118736-04-2)
• EPA Substance Registry System: tert-Butyl[4-(dimethoxymethyl)phenoxy]dimethylsilane(118736-04-2)

Safety Data

• Hazardous Substances Data: 118736-04-2(Hazardous Substances Data)

Usage

General Description

Tert-Butyl[4-(dimethoxymethyl)phenoxy]dimethylsilane is an organosilicon compound with the chemical formula C14H33O4Si. It is composed of a tert-butyl group, a phenoxy group with a dimethoxymethyl substituent, and multiple dimethylsilane groups. This chemical is often used as a protective coating and adhesive in the electronics industry due to its high thermal stability and chemical resistance. It is also used as a reagent in organic synthesis to introduce the tert-butyl and silane functional groups into organic molecules. Additionally, it can act as a water repellent and anti-corrosion agent when applied as a surface treatment.

InChI:InChI=1/C15H26O3Si/c1-15(2,3)19(6,7)18-13-10-8-12(9-11-13)14(16-4)17-5/h8-11,14H,1-7H3

Upstream product

• 67-56-1 methanol 
• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 123-08-0 4-hydroxy-benzaldehyde 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 1251825-30-5 (4-((4R,5R)-4,5-diphenyl-1,3-dioxolan-2-yl) phenoxy)(tertbutyl)dimethylsilane 
• 521274-34-0 phenoxy-acetic acid 1-[2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-5-(2-trityloxy-ethyl)-[1,3]dioxolan-4-ylmethyl]-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl ester 
• 521274-35-1 phenoxy-acetic acid 1-{5-(2-allyloxycarbonylamino-ethyl)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-[1,3]dioxolan-4-ylmethyl}-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl ester 
• 521274-32-8 (5S,6S)-6-((E)-2-{(2R,4R,5R)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-5-((2R,5Z)-2-hydroxy-6-{(1R,3S)-3-[(4-methoxyphenoxy)methoxy]cyclohexyl}hex-5-en-3-ynyl)-4-[2-(trityloxy)ethyl]-[1,3]dioxolan-4-yl}vinyl)-5-ethyl-5,6-dihydro-2H-pyran-2-one 
• 521274-33-9 (5S,6S)-6-{(E)-2-[(2R,4R,5R)-2-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-5-{(3Z,5Z)-(R)-2-hydroxy-6-[(1R,3S)-3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-hexa-3,5-dienyl}-4-(2-trityloxy-ethyl)-[1,3]dioxolan-4-yl]-vinyl}-5-ethyl-5,6-dihydro-pyran-2-one 
• 1053731-78-4 (R)-3-{(E)-(2R,3S)-5-[(2R,4R,5R)-5-Allyl-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-(2-trityloxy-ethyl)-[1,3]dioxolan-4-yl]-2-ethyl-3-triethylsilanyloxy-pent-4-enoyl}-4-benzyl-oxazolidin-2-one 
• 521274-44-2 phenoxy-acetic acid 1-{5-(2-azido-ethyl)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-[1,3]dioxolan-4-ylmethyl}-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl ester 
• 521274-43-1 phenoxy-acetic acid 1-[2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-5-(2-hydroxy-ethyl)-[1,3]dioxolan-4-ylmethyl]-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl ester 
• 521274-27-1 (R)-3-{(E)-(2R,3S)-5-[(2R,4R,5R)-5-Allyl-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-(2-trityloxy-ethyl)-[1,3]dioxolan-4-yl]-2-ethyl-3-hydroxy-pent-4-enoyl}-4-benzyl-oxazolidin-2-one 
• 521274-41-9 S-ethyl (4E,7R)-7-C-allyl-6,7-O-(4-{[tert-butyl(dimethyl)silyl]oxy}benzylidene)-2,4,5-trideoxy-2-ethyl-1-thio-3-O-(triethylsilyl)-6-C-[2-(trityloxy)ethyl]-L-arabino-4-enoate 
• 521274-28-2 ethyl (2Z,4S,5S,6E)-7-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(tritylioxy)ethyl]-[1,3]dioxolan-4-yl}-4-ethyl-5-hydroxyhepta-2,6-dienoate 
• 521274-42-0 (5S,6S)-6-((E)-2-{(2R,4R,5R)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-5-(2,3-dihydroxypropyl)-4-[2-(trityloxy)ethyl]-[1,3]dioxolan-4-yl}vinyl)-5-ethyl-5,6-dihydro-2H-pyran-2-one 
• 521274-29-3 (5S,6S)-6-((E)-2-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(trityloxy)ethyl]-[1,3]dioxolan-4-yl}vinyl)-5-ethyl-5,6-dihydro-2H-pyran-2-one 
• 521274-30-6 [(2R,4R,5R)-2-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-5-[(E)-2-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-5-(2-trityloxy-ethyl)-[1,3]dioxolan-4-yl]-acetaldehyde 

Relevant articles and documents

Chemoselective Nucleophilic Functionalizations of Aromatic Aldehydes and Acetals via Pyridinium Salt Intermediates

The development of a novel chemoselective functionalization can diversify the strategy for synthesizing the target molecules. The perfect chemoselectivity between aromatic and aliphatic aldehydes is difficult to achieve by the previous methods. The aromatic aldehyde-selective nucleophilic addition in the presence of aliphatic aldehydes was newly accomplished. Namely, the aromatic aldehyde-selective nucleophilic addition using arenes and allyl silanes proceeded in the presence of trialkylsilyl triflate and 2,2′-bipyridyl, while the aliphatic aldehydes completely remained unchanged. The reactive pyridinium-type salt intermediate derived from an aromatic aldehyde chemoselectively underwent the nucleophilic substitution. Moreover, the aromatic acetals as the protected aldehydes could be directly transformed into similar pyridinium salt intermediates, which reacted with various nucleophiles coexisting with the aliphatic aldehydes.

Protection of diols with 4-(tert-Butyldimethylsilyloxy)Benzylidene acetal and its deprotection: (4-((4R,5R)-4,5-diphenyl-1,3-dioxolan-2-yl)phenoxy) (tertbutyl)dimethylsilane

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4-(tert-Butyldimethylsilyloxy)benzylidene acetal: A novel benzylidene-type protecting group for 1,2-diols

A novel 1,2-diol-protecting group, p-silyloxybenzylidene group, has been developed. In addition to the stepwise deprotection conditions including desilylation and the subsequent acidic hydrolysis of the p-hydroxybenzylidene group in AcOH-THF-H2O, we have established the one-pot deprotection under basic conditions [K2CO3 (5equiv), NH 2OH·HCl (5equiv), and CsF (1equiv) in MeOH-H2O].