5908-41-8

Basic information

• Product Name: phenyl(triMethylsilyl)Methanone
• Synonyms: phenyl(triMethylsilyl)Methanone
• CAS NO: 5908-41-8
• Molecular Formula: C₁₀H₁₄OSi
• Molecular Weight: 178.30306
• Mol File: 5908-41-8.mol

Chemical Properties

• Boiling Point: 214.5°C at 760 mmHg
• Flash Point: 83.5°C
• Appearance: /
• Density: 0.939g/cm³
• Vapor Pressure: 0.155mmHg at 25°C
• Refractive Index: 1.483
• CAS DataBase Reference: phenyl(triMethylsilyl)Methanone(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl(triMethylsilyl)Methanone(5908-41-8)
• EPA Substance Registry System: phenyl(triMethylsilyl)Methanone(5908-41-8)

Safety Data

• Hazardous Substances Data: 5908-41-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Phenyl(triMethylsilyl)Methanone is utilized as a reagent in organic synthesis for its ability to facilitate the formation of various organic compounds. Its presence aids in achieving desired chemical reactions and contributes to the development of new molecules with specific properties.
Used in Chemical Research and Development:
In the field of chemical research and development, phenyl(triMethylsilyl)Methanone is employed as an important tool. Its unique structure and the protective nature of the trimethylsilyl group make it a valuable asset in the exploration of new chemical pathways and the creation of innovative compounds.
Used in Protective Group Chemistry:
Phenyl(triMethylsilyl)Methanone is used as a protective group in organic chemistry to prevent unwanted reactions at specific positions in a molecule. This selective protection allows chemists to control the reactivity of certain functional groups, enabling the synthesis of complex organic molecules with greater precision and efficiency.

InChI:InChI=1/C10H14OSi/c1-12(2,3)10(11)9-7-5-4-6-8-9/h4-8H,1-3H3

Upstream product

• 17955-46-3 trimethylsilyltributyltin 
• 98-88-4 benzoyl chloride 
• 56253-59-9 α-Trimethylsilylbenzyl Phenyl Selenid 
• 75-77-4 chloro-trimethyl-silane 
• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 1923-01-9 trimethyl(1-phenylvinyl)silane 
• 98-81-7 1-bromovinylbenzene 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 591-50-4 iodobenzene 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 201230-82-2 carbon monoxide 
• 31608-80-7 (trimethylsilyl)trimethylgermane 
• 18255-05-5 benzyl phenyl selenide 

Downstream Products

• 91-01-0 1,1-Diphenylmethanol 
• 1733-63-7 1,2,2-triphenylethan-1-one 
• 58753-28-9 3-benzoylcyclohexan-1-one 
• 134-81-6 benzil 
• 1689-64-1 9-Fluorenol 
• 1603-73-2 fluoren-9-yl-phenyl ketone 
• 27397-33-7 1H-inden-3-yltrimethylsilane 
• 83-33-0 inden-1-one 
• 144968-88-7 2,2,3,3,3-Pentafluoro-1-phenyl-1-trimethylsilanyl-propan-1-ol 
• 60815-12-5 2,3-dihydro-2-hydroxy-2-phenyl-1H-inden-1-one 
• 36190-35-9 Dimethyl trimethylsilyloxybenzylphosphonate 
• 31675-43-1 diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate 
• 6270-17-3 ethyl 3-benzoylpropanoate 

Relevant articles and documents

Anodic oxidation of 2-alkyl-2-trialkylsilyl-1, 3-dithianes a facile preparation of acylsilanes

Acylsilanes can easily be prepared by the anodic oxidation of 2-alkyl-2-trialkylsilyl-1, 3-dithianes with a platinum anode in wet acetonitrile. This electrochemical reaction provides a general and convenient access to aroyl, saturated and α, β-unsaturated

Synthesis of aryl and alkyl acylsilanes using trimethyl(tributylstannyl)silane

Palladium catalyzed coupling of acid chlorides and trimethyl(tribuhfistannyl)silane proves to be a convenient method for the preparation of both aromatic and aliphatic acylsilanes.

Visible-Light Mediated Tryptophan Modification in Oligopeptides Employing Acylsilanes

A method for the selective tryptophan modification and labelling of tryptophan-containing peptides is described. Photoirradiation of acylsilanes generates reactive siloxycarbenes which undergo H?N-insertion into the indole moiety of tryptophan to give stable silyl protected hemiaminals. This method is successfully applied to chemically modify various tryptophan containing oligopeptides. The method enables the selective introduction of alkynes to peptides that are eligible for further alkyne-azide click chemistry. In addition, the dansyl fluorophore can be conjugated to a peptide using this approach.

Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions

We report the facile amide-forming ligation of acylsilanes with hydroxylamines (ASHA ligation) under aqueous conditions. The ligation is fast, chemoselective, mild, high-yielding and displays excellent functional-group tolerance. Late-stage modifications of an array of marketed drugs, peptides, natural products, and biologically active compounds showcase the robustness and functional-group tolerance of the reaction. The key to the success of the reaction could be the possible formation of the strong Si?O bond via a Brook-type rearrangement. Given its simplicity and efficiency, this ligation has the potential to unfold new applications in the areas of medicinal chemistry and chemical biology.

Visible-Light-Induced Catalyst-Free Carboxylation of Acylsilanes with Carbon Dioxide

Intermolecular carbon-carbon bond formation between acylsilanes and carbon dioxide (CO2) was achieved by photoirradiation under catalyst-free conditions. In this reaction, siloxycarbenes generated by photoisomerization of the acylsilanes added to the C═O bond of CO2 to give α-ketocarboxylates, which underwent hydrolysis to afford α-ketocarboxylic derivatives in good yields. Control experiments suggest that the generated siloxycarbene is likely to be from the singlet state (S1) of the acylsilane and the addition to CO2 is not in a concerted manner.

Controllable one-pot synthesis for scaffold diversity: Via visible-light photoredox-catalyzed Giese reaction and further transformation

This study presents a controllable one-pot synthesis for constructing valuable scaffolds (alcohols, 2,3-dihydrofurans, α-cyano-γ-butyrolactones, and γ-butyrolactones) via a visible-light photoredox-catalyzed Giese reaction and further transformation. This

Ruthenium-Catalyzed Brook Rearrangement Involved Domino Sequence Enabled by Acylsilane-Aldehyde Corporation

A ruthenium-catalyzed [1,2]-Brook rearrangement involved domino sequence is presented to prepare highly functionalized silyloxy indenes with atomic- and step-economy. This domino reaction is triggered by acylsilane-directed C-H activation, and the aldehyde controlled the subsequent enol cyclization/Brook Rearrangement other than β-H elimination. The protocol tolerates a broad substitution pattern, and the further synthetic elaboration of silyloxy indenes allows access to a diverse range of interesting indene and indanone derivatives.

Preparation of Functionalized Acylsilanes by Diol Cleavage of Cyclic 1,2-Dihydroxysilanes

We report a study on diol cleavage of cyclic 1,2-dihydroxysilanes for the preparation of functionalized acylsilanes. Sodium periodate turned out to be an efficient reagent for this transformation, resulting in good to excellent yields. The method is chara

Synthesis of Acylsilanes via Catalytic Dedithioacetalization of 2-Silylated 1,3-Dithianes with 30% Hydrogen Peroxide

Acylsilanes were obtained efficiently from dedithioacetalization of 2-silylated 1,3-dithianes using 30% hydrogen peroxide catalyzed by iron(III) acetylacetonate-sodium iodide. The use of niobium(V) chloride as a catalyst instead of iron(III) acetylacetonate was also effective, except in synthesizing some acyltrimethylsilanes.

Oxidative [1,2]-Brook Rearrangements Exploiting Single-Electron Transfer: Photoredox-Catalyzed Alkylations and Arylations

Oxidative [1,2]-Brook rearrangements via hypervalent silicon intermediates induced by photoredox-catalyzed single-electron transfer have been achieved, permitting the formation of reactive radical species that can engage in alkylations and arylations.