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667951

Sigma-Aldrich

(4-Methoxyphenyl)dimethylsilanol

96%

Synonym(s):

(p-Methoxyphenyl)dimethylsilanol

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About This Item

Linear Formula:
((CH3O)C6H4)Si(CH3)2OH
CAS Number:
22868-26-4
Molecular Weight:
182.29
MDL number:
MFCD08276887
UNSPSC Code:
12352103
PubChem Substance ID:
24884950
NACRES:
NA.22

Assay

96%

refractive index

n20/D 1.522

density

1.101 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

COc1ccc(cc1)[Si](C)(C)O

InChI

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

InChI key

DDLYKNBMTGBOQY-UHFFFAOYSA-N

Application

(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.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
08521CE

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Phosphine oxides as stabilizing ligands for the palladium-catalyzed cross-coupling of potassium aryldimethylsilanolates
Denmark SE, et al.
Tetrahedron, 63(26), 5730-5738 (2007)
Organosilanes for Cross-coupling
Aldrich Chemfiles, 6(5), 7-9 (2006)
Palladium-Catalyzed Cross-Coupling Reactions of Substituted Aryl (dimethyl) silanols
Denmark SE and Ober MH
Advanced Synthesis & Catalysis, 346(13-15), 1703-1714 (2004)
Cross-coupling reactions of arylsilanols with substituted aryl halides
Denmark SE and Ober MH
Organic Letters, 5(8), 1357-1360 (2003)
Palladium-Catalyzed Cross-Coupling Reactions of Substituted Aryl (dimethyl) silanols
Denmark SE and Ober MH
advanced synthesis and catalysis, 346(13-15), 1703-1714 (2004)
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Organosilanols

Pd-catalyzed cross-coupling of silicon compounds offers an alternative in synthetic chemistry.

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