22868-26-4

Basic information

• Product Name: (4-METHOXYPHENYL)DIMETHYLSILANOL, 96%
• Synonyms: Silanol,(4-methoxyphenyl)dimethyl- (9CI); Silanol, (p-methoxyphenyl)dimethyl- (8CI);(4-Methoxyphenyl)dimethylsilanol; (p-Methoxyphenyl)dimethylhydroxysilane;(p-Methoxyphenyl)dimethylsilanol
• CAS NO: 22868-26-4
• Molecular Formula: C₉H₁₄O₂Si
• Molecular Weight: 182.29
• Product Categories: Chemical Synthesis;Organometallic Reagents;Organosilicon;Silanols
• Mol File: 22868-26-4.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 248.82°C at 760 mmHg
• Flash Point: 110 °C
• Appearance: /
• Density: 1.101 g/mL at 25 °C
• Vapor Pressure: 0.013mmHg at 25°C
• Refractive Index: n 20/D 1.522
• Storage Temp.: 2-8°C
• PKA: 14.49±0.53(Predicted)
• CAS DataBase Reference: (4-METHOXYPHENYL)DIMETHYLSILANOL, 96%(CAS DataBase Reference)
• NIST Chemistry Reference: (4-METHOXYPHENYL)DIMETHYLSILANOL, 96%(22868-26-4)
• EPA Substance Registry System: (4-METHOXYPHENYL)DIMETHYLSILANOL, 96%(22868-26-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 22868-26-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 22868-26-4 differently. You can refer to the following data:
1. (4-Methoxyphenyl)dimethylsilanol is a useful silicon nucleophile for Pd-catalyzed cross-coupling.
2. (4-Methoxyphenyl)dimethylsilanol can be used:As a starting material in the Pd-catalyzed cross-coupling reactions with various aryl halides to obtain biaryl compounds using Cs2CO3 base.As a starting material to prepare potassium (4-methoxyphenyl)dimethylsilanolate, which in turn is used to synthesize biaryl derivatives by reacting with aryl bromides.As a co-catalyst along with Mo(CO)6 applicable in the 4-decyne metathesis.

InChI:InChI=1/C9H14O2Si/c1-11-8-4-6-9(7-5-8)12(2,3)10/h4-7,10H,1-3H3

Upstream product

• 140642-59-7 ethoxy-(4-methoxy-phenyl)-dimethyl-silane 
• 1432-38-8 (p-methoxyphenyl)dimethylsilane 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 1415919-35-5 dimethyl(4-methoxyphenyl)silyl formate 
• 2372-33-0 chlorodimethyl(4-methoxyphenyl)silane 
• 80986-52-3 dimethyl (1-methoxyprop-2-enyl)phosphonate 
• 17903-46-7 [(4-methoxyphenyl)dimethylsilyl]methyl chloride 
• 106773-97-1 C₁₀H₁₆O₂Si 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 541-05-9 Hexamethylcyclotrisiloxane 
• 696-62-8 para-iodoanisole 
• 4199-03-5 1-(4-Methoxyphenyl)-1,1,2,2,2-pentamethyldisilane 

Downstream Products

• 67-56-1 methanol 
• 24537-53-9 1-(4-Methoxy-phenyl)-1,1,3,3,3-pentamethyl-disiloxane 
• 173464-57-8 (E)-3-(4-methoxyphenyl)acrylic acid butyl ester 
• 637-69-4 4-Methoxystyrene 
• 613-37-6 4-methoxylbiphenyl 
• 834-14-0 p-benzylanizole 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 92-52-4 biphenyl 
• 53040-92-9 4-(4-tolyl)anisole 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 
• 27331-33-5 1-(4-methoxyphenyl)naphthalene 
• 20013-55-2 4'-methoxy-2-nitrobiphenyl 
• 858672-69-2 potassium (4-methoxyphenyl)dimethylsilanololate 
• 132312-99-3 1-methoxy-4-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]benzene 

Relevant articles and documents

Selective Electrochemical Hydrolysis of Hydrosilanes to Silanols via Anodically Generated Silyl Cations

The first electrochemical hydrolysis of hydrosilanes to silanols under mild and neutral reaction conditions is reported. The practical protocol employs commercially available and cheap NHPI as a hydrogen-atom transfer (HAT) mediator and operates at room temperature with high selectivity, leading to various valuable silanols in moderate to good yields. Notably, this electrochemical method exhibits a broad substrate scope and high functional-group compatibility, and it is applicable to late-stage functionalization of complex molecules. Preliminary mechanistic studies suggest that the reaction appears to proceed through a nucleophilic substitution reaction of an electrogenerated silyl cation with H2O.

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.

Silicon-center chiral silicon-oxygen compound and preparation method thereof

The invention belongs to the field of chiral silicon synthesis, and discloses a silicon-center chiral silicon-oxygen compound. The compound has a structure represented by general formula I shown in the specification. In the formula I, X is Si(R)n or a formula also shown in the specification, R is selected from alkyl, cycloalkyl and aryl, R is selected from alkyl, substituted phenyl and aryl, R is selected from alkyl, phenyl and substituted phenyl, n is 3, the three R are the same or different, R is selected from hydrogen and (C1-C4) alkyl, m is selected from 0, 1, 2 and 3, and Y is selected from substituted phenyl, substituted pyrenyl, aryl, heteroaryl and cycloalkyl. The invention also discloses a preparation method of the compound. Various highly functionalized chiral siloxanes and silyl ethers are obtained with good chemical, regional and stereo control and high yield, the variety of silicon center chiral compounds is expanded, and the method has the advantages of high enantioselectivity, wide substrate application range, mild reaction conditions, atom economy and the like. In addition, the compound provided by the invention has a huge application prospect in chiral organic photoelectric materials.