3959-13-5

Basic information

• Product Name: methylphenylsilanediol
• Synonyms: methylphenylsilanediol;Methyldihydroxyphenylsilane;Methylphenyldihydroxysilane;Phenyl(methyl)dihydroxysilane;Einecs 223-562-0;Silanediol, methylphenyl-
• CAS NO: 3959-13-5
• Molecular Formula: C₇H₁₀O₂Si
• Molecular Weight: 154.2386
• EINECS: 223-562-0
• Mol File: 3959-13-5.mol

Chemical Properties

• Boiling Point: 250.6 °C at 760 mmHg
• Flash Point: 105.4 °C
• Appearance: /
• Density: 1.12 g/cm³
• Vapor Pressure: 0.0112mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: methylphenylsilanediol(CAS DataBase Reference)
• NIST Chemistry Reference: methylphenylsilanediol(3959-13-5)
• EPA Substance Registry System: methylphenylsilanediol(3959-13-5)

Safety Data

• Hazardous Substances Data: 3959-13-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methylphenylsilanediol is used as a reagent for the synthetic preparation of (tetramethylnapthalenyl)silanol derivatives. These derivatives are of interest due to their potential activity as selective inhibitors of adult T-cell leukemia (ATL). methylphenylsilanediol plays a crucial role in the development of novel therapeutic agents targeting specific types of cancer.
Used in Chemical Research:
In the field of chemical research, methylphenylsilanediol serves as a valuable compound for studying the properties and reactions of organosilicon compounds. Its unique structure allows for exploration into various chemical reactions and potential applications in material science and organic synthesis.

InChI:InChI=1/C7H10O2Si/c1-10(8,9)7-5-3-2-4-6-7/h2-6,8-9H,1H3

Upstream product

• 31650-28-9 bis(2-thienyl)methylphenylsilane 
• 766-08-5 methylphenylsilane 
• 3027-21-2 dimethoxy(methyl)phenylsilane 
• 149-74-6 dichloromethylphenylsilane 
• 775-56-4 diethoxy-methyl-phenyl-silane 
• 75-54-7 Dichloromethylsilane 

Downstream Products

• 56764-49-9 C₉H₁₄Cl₄O₂Si₃ 
• 64793-19-7 C₁₅H₂₈Cl₂O₆Si₃ 
• 56792-10-0 C₁₁H₁₄Cl₄O₂Si₃ 
• 64793-13-1 2,2,6,6-Tetraethoxy-4,4,8-trimethyl-8-phenyl-[1,3,5,7,2,4,6,8]tetroxatetrasilocane 
• 64793-12-0 2,2,6,6-Tetraethoxy-4,8-dimethyl-4,8-diphenyl-[1,3,5,7,2,4,6,8]tetroxatetrasilocane 
• 56764-59-1 C₂₉H₃₆Cl₆O₆Si₇ 
• 56764-51-3 C₇H₈Cl₆O₂Si₃ 
• 56764-50-2 C₁₉H₁₈Cl₄O₂Si₃ 
• 17962-87-7 1,5-dichloro-1,1,3,5,5-pentamethyl-3-phenyltrisiloxane 
• 613-37-6 4-methoxylbiphenyl 
• 53040-92-9 4-(4-tolyl)anisole 
• 1415933-87-7 1,5-divinyl-1,1,5,5-tetramethoxy-3-phenyl-3-methyltrisiloxane 
• 106582-62-1 1-hydro-1,3,3,5,7,7-hexamethyl-5-phenylcyclotetrasiloxane 
• 499777-17-2 1,1,3,5,5-pentamethyl-3-phenyltrisiloxane-1,5-diol 

Relevant articles and documents

METHOD FOR PRODUCING SILANOLS AND NOVEL SILANOLS

PROBLEM TO BE SOLVED: To provide a method for efficiently producing silanols useful as functional chemicals, and to provide novel silanols. SOLUTION: There is provided a method for producing silanols including a reaction step of reacting alkoxysilanes having Si-OR bonds (R represents a hydrocarbon group having 1 to 6 carbon atoms) with water or heavy water in the presence of a catalyst, wherein a method for producing silanols having an Si-OR' bond (R' represents a hydrogen atom or a deuterium atom) is characterized in that the catalyst is an inorganic solid acid catalyst having a regular pore structure. There is also provided novel silanols obtained thereby. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Synthesis and Hydrogen-Bond Patterns of Aryl-Group Substituted Silanediols and -triols from Alkoxy- and Chlorosilanes

Organosilanols typically show a high condensation tendency and only exist as stable isolable molecules under very specific steric and electronic conditions at the silicon atom. In the present work, various novel representatives of this class of compounds were synthesized by hydrolysis of alkoxy- or chlorosilanes. Phenyl, 1-naphthyl, and 9-phenanthrenyl substituents at the silicon atom were applied to systematically study the influence of the aromatic substituents on the structure and reactivity of the compounds. Chemical shifts in 29Si NMR spectroscopy in solution, correlated well with the expected electronic situation induced by the substitution pattern on the Si atom. 1H NMR studies allowed the detection of strong intermolecular hydrogen bonds. Single-crystal X-ray structures of the alkoxides and the chlorosilanes are dominated by π-π interactions of the aromatic systems, which are substituted by strong hydrogen bonding interactions representing various structural motifs in the respective silanol structures.

O2-enhanced catalytic activity of gold nanoparticles in selective oxidation of hydrosilanes to silanols

O2 acts as a nonconsumed activator for gold nanoparticles (AuNPs) in the oxidation of hydrosilanes to silanols with water under O2 atmosphere, providing an acceleration of more than 200 times relative to the reaction rate under Ar atmosphere. The AuNP catalyst under aerobic conditions exhibits high activity in the oxidation with high turnover numbers (1230000). Various hydrosilanes including less-reactive bulky ones can be converted to the corresponding silanols in excellent yields. Moreover, the present AuNP catalyst is reusable while maintaining the high performance.

Organosilicon compounds as adult T-cell leukemia cell proliferation inhibitors

Aggressive forms of adult T-cell leukemia (ATL) respond poorly to conventional anticancer chemotherapy, and new lead compounds are required for the development of drugs to treat this fatal disease. Recently, we developed ATL cell-selective proliferation inhibitors based on a tetrahydrotetramethylnaphthalene (TMN) skeleton 1, and here we report the design and synthesis of silicon analogs of TMN derivatives. Among them, compound 13 showed the most potent growth-inhibitory activity towards the ATL cell line S1T, though its selectivity for S1T over the non-ATL cell line MOLT-4 was only moderate. This result, as well as computational studies, suggests that sila-substitution (C/Si exchange) is useful for structure optimization of these inhibitors.

Bis(2-thienyl)silanes: new, versatile precursors to arylsilanediols

Silanediols have been shown to be effective bioisosteres for the hydrated carbonyl group. Current methods for the formation of silanediols place a number of constraints on how and where this functionality may be used. A range of arylsilanes that would allow both the formation of arylsilanediols and that are also compatible with multi-step synthetic routes, have been investigated as possible precursors to silanediols. Through this study bis(2-furyl)silanes and, in particular, bis(2-thienyl)silanes have been identified as practical precursors to arylsilanediols.

Palladium-Catalyzed Cross-Coupling of Silanols, Silanediols, and Silanetriols Promoted by Silver(I) Oxide

Palladium-catalyzed cross-coupling of aryl- or alkenylsilanols, silanediols, and silanetriols with a variety of iodoarenes by the catalysis of palladium(0) and in the presence of silver(I) oxide furnished the coupling products in good to excellent yields. The reactions of silanediols or silanetriols under similar conditions proceeded much faster than those of silanols to afford the corresponding coupling products in excellent yields within shorter reaction periods (5-12 h). The measurement of the X-ray diffraction (XRD) pattern of the silver residue after the reaction revealed that silver(I) oxide was converted to silver(I) iodide.

Nucleophilic fluorination of alkoxysilane with alkali metal salts of perfluorinated complex anions. Part 2

Alkali metal salts of perfluorinated complex anions have been used to effect nucleophilic fluorination of alkyl-, arylalkyl- and arylalkoxy-silanes both in the presence and absence of solvent. Near-quantitative yields of fluorinated silanes are obtained using equimolar quantities of fluoride ion equivalents and alkoxysilanes. In certain cases, intermediate organoboron and organophosphorus compounds derived from the corresponding complex anions and alkoxysilanes are identified in the reaction mixtures, and based on these intermediates a mechanism of reaction has been proposed.

Procedures for the preparation of silanols

Two procedures are described for the preparation of silanols and silanediols from the corresponding chlorosilanes.The first procedure, a two-phase hydrolysis-extraction process, is- particularly convenient and suited to the preparation of a wide range of mono-silanols.Hydrolysis of dichlorosilanes by this procedure gives varied results depending on the structure of the dichlorosilane and specific reaction conditions.The second procedure, a modification of a published procedure, is especially beneficial for the preparation of silanols and silanediols prone to undergo self-condensation. Key words: Silicon; Hydrolysis; Self-condensation; Silanols

Novel n[meth)allyloxy(meth)allylphenyl]maleimides and thermosetting imido copolymers prepared therefrom

Novel N-[(meth)allyloxy-mono-/di(meth)allylphenyl]maleimides, in admixture with at least one N-[(meth)allyloxyphenyl]maleimide, are reacted with at least one bismaleimide, and optionally a hydroxylated organosilicon compound, in the presence of an imidazole compound, to obtain mechanically improved thermosetting imido copolymerizates well adapted for the production of, e.g., coatings, adhesive bondings, laminates and composites.