116700-73-3

Basic information

• Product Name: 2-(((Tert-Butyldimethylsilyl)Oxy)Methyl)Prop-2-En-1-Ol
• Synonyms: 2-(((Tert-Butyldimethylsilyl)Oxy)Methyl)Prop-2-En-1-Ol;2-Propen-1-ol, 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-;2-(tert-butyl-dimethyl-silanyloxymethyl)-prop-2-en-1-ol;2-(((Tert-Butyldimethylsilyl)Oxy)Methyl)Prop-2-En-1-Ol(WXC00313)
• CAS NO: 116700-73-3
• Molecular Formula: C₁₀H₂₂O₂Si
• Molecular Weight: 202.36598
• Mol File: 116700-73-3.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 236.2±28.0 °C(Predicted)
• Appearance: /
• Density: 0.886±0.06 g/cm3(Predicted)
• PKA: 14.48±0.10(Predicted)
• CAS DataBase Reference: 2-(((Tert-Butyldimethylsilyl)Oxy)Methyl)Prop-2-En-1-Ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(((Tert-Butyldimethylsilyl)Oxy)Methyl)Prop-2-En-1-Ol(116700-73-3)
• EPA Substance Registry System: 2-(((Tert-Butyldimethylsilyl)Oxy)Methyl)Prop-2-En-1-Ol(116700-73-3)

Safety Data

• Hazardous Substances Data: 116700-73-3(Hazardous Substances Data)

Usage

Physical state

Colorless, flammable liquid

Odor

Faint

Use

Reagent in organic synthesis, protective agent for hydroxyl groups in organic compounds

Applications

Modification of natural products, synthesis of pharmaceuticals, agrochemicals, and functional materials

Properties

Ability to form stable silicon-oxygen bonds, useful in chemical transformations and as a protecting group in the synthesis of complex organic molecules

Importance

Versatile and valuable reagent in organic chemistry

Upstream product

• 1871-57-4 2-chloromethyl-3-chloroprop-1-ene 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 3513-81-3 2-(Hydroxymethyl)allyl alcohol 
• 144828-45-5 2-(tert-butyl-dimethyl-silanyloxymethyl)-acrylic acid methyl ester 
• 111160-83-9 tert-butyldimethyl(2-methylallyloxy)silane 
• 116700-77-7 ethyl 2-({[tert-butyl(dimethyl)silyl]oxy}methyl)acrylate 

Downstream Products

• 881398-70-5 2-[(allyl-benzyl-amino)-methyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid methyl ester 
• 881398-72-7 2-(allyl-benzyl-carbamoyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid methyl ester 
• 1613059-49-6 2-(((tert-butyldimethylsilyl)oxy)methyl)allyl 4-(dimethylamino)benzoate 
• 1613059-32-7 (S)-3-((tert-butyldimethylsilyl)oxy)-2-hydroxy-2-(hydroxymethyl)propyl 4-(dimethylamino)benzoate 

Relevant articles and documents

Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors in staphylococcus aureus

Interfering with bacterial cell-to-cell communication is a promising strategy to combat antimicrobial resistance. The natural product hamamelitannin and several of its analogues have been identified as quorum sensing inhibitors. In this paper the synthesi

Synthesis of novel 6,11-o-bridged bicyclic ketolides via a palladium-catalyzed bis-allylation

(Chemical equation presented) A bridging chemistry process was developed to form an ether bridge between 6-O and 11-O of erythromycin A via a tandem or stepwise palladium-catalyzed bis-π-allylation. By applying this bridging process, new 6,11-O-bridged bicyclic ketolides (BBKs) were synthesized. These BBKs showed good antibacterial activities against the macrolide-susceptible strains as well as mef-resistant strains and served as a good core for further modifications to study the structure-activity relationship (SAR) and to overcome bacterial resistance.

All-Carbon [3+3] Oxidative Annulations of 1,3-Enynes by Rhodium(III)-Catalyzed C-H Functionalization and 1,4-Migration

1,3-Enynes containing allylic hydrogens cis to the alkyne function as three-carbon components in rhodium(III)-catalyzed, all-carbon [3+3] oxidative annulations to produce spirodialins. The proposed mechanism of these reactions involves the alkenyl-to-ally

Enantioselective hydroesterificative cyclization of 1,6-enynes to chiral γ-lactams bearing a quaternary carbon stereocenter

A palladium-catalyzed asymmetric hydroesterification-cyclization of 1,6-enynes with CO and alcohol was developed to efficiently prepare a variety of enantioenriched γ-lactams bearing a chiral quaternary carbon center and a carboxylic ester group. The approach featured good to high chemo-, region-, and enantioselectivities, high atom economy, and mild reaction conditions as well as broad substrate scope. The correlation between the multiple selectivities of such process and the N-substitutes of the amide linker in the 1,6-enyne substrate has been depicted by the crystallographic evidence and control experiments.

Stereoselective Modification of N-(α-Hydroxyacyl)-glycinesters via Palladium-Catalyzed Allylic Alkylation

N-(α-Hydroxyacyl)-glycinesters can be used as excellent nucleophiles in Pd-catalyzed allylic alkylation. The method allows for the stereoselective introduction of a wide range of side chains, including highly functionalized ones. Both diastereomers can be accessed through variation of the reaction conditions. Furthermore, the use of stannylated carbonates introduces vinylstannane motifs, which are eligible for subsequent C-C coupling reactions.