188404-95-7

Basic information

• Product Name: Silanol, dimethyl(2-methylphenyl)-
• CAS NO: 188404-95-7
• Molecular Formula: C9H14OSi
• Molecular Weight: 166.295
• Mol File: 188404-95-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Silanol, dimethyl(2-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silanol, dimethyl(2-methylphenyl)-(188404-95-7)
• EPA Substance Registry System: Silanol, dimethyl(2-methylphenyl)-(188404-95-7)

Safety Data

• Hazardous Substances Data: 188404-95-7(Hazardous Substances Data)

Upstream product

• 95-46-5 2-methylphenyl bromide 
• 541-05-9 Hexamethylcyclotrisiloxane 
• 188404-92-4 (o-methylphenyl)dimethylsilane 

Downstream Products

• 605-39-0 2,2'-dimethyl-1,1'-biphenyl 
• 47230-38-6 diethyl biphenyl-4,4'-dicarboxylate 
• 134694-65-8 ethyl 2'-methylbiphenyl-4-carboxylate 
• 163977-61-5 butyl (2E)-3-(2-methylphenyl)acrylate 

Relevant articles and documents

Photocatalyzed cross-dehydrogenative coupling of silanes with alcohols and water

An efficient method for the dehydrogenative coupling of silanes with alcohols under photocatalysis was developed. The reaction proceeded in the presence of Ru(bpy)3Cl2(0.5 mol%) under visible light irradiation in acetonitrile at room temperature. The developed methodology was also applicable for the synthesis of silanols using water as a coupling partner.

Novel carbon-carbon bond formation through Mizoroki-Heck type reaction of silanols and organotin compounds

The reaction of dimethyl(phenyl)silanol with butyl acrylate in the presence of a stoichiometric amount of Pd(OAc)2 or by a combined use of 0.1 molar amount of Pd(OAc)2 and Cu(OAc)2/LiOAc (molar ratio 3/2) gave butyl cinnamate in 76% or 57% yield, respectively. The similar reaction with tributyl(phenyl)tin also proceeded in 77% yield. The organotin compound was shown to react faster than the sitanol, although the tin reagent sometimes induced undesirable homocoupling, while the reaction with silanol did not give such by-product.

Kinetic Control in the Cleavage of Unsymmetrical Disilanes

A series of 12 phenyl-substituted arylpentamethyldisilanes 1a-1 have been synthesized in order to examine the regioselectivity of their nucleophilic Si,Si bond cleavage reactions under Still's conditions (MeLi/HMPA/0°C). It has been found that the sensitivity of these reactions to the electronic effects of the substituents in the phenyl ring could be described by the Hammett-type equation log(kA/kB) = 0.4334 + 2.421(Σσ); (correlation coefficient R = 0.983). The kA/kB ratio represents the relative rate of attack at silicon atom A (linked to the aryl ring) or at silicon atom B (away from the aryl ring) of the unsymmetrical disilanes. Thus, the present investigation shows that the earlier belief according to which the nucleophilic cleavage of unsymmetrical disilanes always produces the more stable silyl anionic species (thermodynamic control) should be abandoned, or at least seriously amended: kinetic factors appear to exert a primary influence on the regioselectivity of such reactions. Since the two major kinetic factors (i.e., electrophilic character of and steric hindrance at a given silicon atom) have opposite effects on the orientation of the reaction, it may happen that kinetic and thermodynamic control lead to the same result. For some of the unsymmetrical disilanes studied, the major reaction path was not the Si,Si bond cleavage; instead, Si-aryl bond breaking occurred, producing the corresponding aryl anions.