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

• 104-92-7 1-bromo-4-methoxy-benzene 
• 541-05-9 Hexamethylcyclotrisiloxane 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 1432-38-8 (p-methoxyphenyl)dimethylsilane 
• 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 
• 696-62-8 para-iodoanisole 
• 140642-59-7 ethoxy-(4-methoxy-phenyl)-dimethyl-silane 
• 4199-03-5 1-(4-Methoxyphenyl)-1,1,2,2,2-pentamethyldisilane 

Downstream Products

• 173464-57-8 (E)-3-(4-methoxyphenyl)acrylic acid butyl ester 
• 2143-90-0 4-methoxy-4'-nitrobiphenyl 
• 613-37-6 4-methoxylbiphenyl 
• 834-14-0 p-benzylanizole 
• 581-80-6 4,4'-bis(trifluoromethyl)biphenyl 
• 10355-12-1 1-(4-methoxyphenyl)-4-(trifluoromethyl)benzene 
• 47230-38-6 diethyl biphenyl-4,4'-dicarboxylate 
• 732-80-9 4'-methoxy-biphenyl-4-carboxylic acid ethyl ester 
• 858672-69-2 potassium (4-methoxyphenyl)dimethylsilanololate 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 92-52-4 biphenyl 
• 1528-74-1 4,4'-dinitrobiphenyl 
• 637-69-4 4-Methoxystyrene 
• 67-56-1 methanol 

Relevant articles and documents

Metal-free hydrogen evolution cross-coupling enabled by synergistic photoredox and polarity reversal catalysis

A synergistic combination of photoredox and polarity reversal catalysis enabled a hydrogen evolution cross-coupling of silanes with H2O, alcohols, phenols, and silanols, which afforded the corresponding silanols, monosilyl ethers, and disilyl ethers, respectively, in moderate to excellent yields. The dehydrogenative cross-coupling of Si-H and O-H proceeded smoothly with broad substrate scope and good functional group compatibility in the presence of only an organophotocatalyst 4-CzIPN and a thiol HAT catalyst, without the requirement of any metals, external oxidants and proton reductants, which is distinct from the previously reported photocatalytic hydrogen evolution cross-coupling reactions where a proton reduction cocatalyst such as a cobalt complex is generally required. Mechanistically, a silyl cation intermediate is generated to facilitate the cross-coupling reaction, which therefore represents an unprecedented approach for the generation of silyl cationviavisible-light photoredox catalysis.

Catalytic Enantioselective Dehydrogenative Si-O Coupling to Access Chiroptical Silicon-Stereogenic Siloxanes and Alkoxysilanes

A rhodium-catalyzed enantioselective construction of triorgano-substituted silicon-stereogenic siloxanes and alkoxysilanes is developed. This process undergoes a direct intermolecular dehydrogenative Si-O coupling between dihydrosilanes with silanols or alocohols, giving access to a variety of highly functionalized chiral siloxanes and alkoxysilanes in decent yields with excellent stereocontrol, that significantly expand the chemical space of the silicon-centered chiral molecules. Further utility of this process was illustrated by the construction of CPL-active (circularly polarized luminescence) silicon-stereogenic alkoxysilane small organic molecules. Optically pure bis-alkoxysilane containing two silicon-stereogenic centers and three pyrene groups displayed a remarkable glum value with a high fluorescence quantum efficiency (glum = 0.011, φF = 0.55), which could have great potential application prospects in chiral organic optoelectronic materials.

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.