3-(Phenyldimethylsilyl)acrylic acid

Base Information

• Chemical Name: 3-(Phenyldimethylsilyl)acrylic acid
• CAS No.: 109053-88-5
• Molecular Formula: C₁₁H₁₄O₂Si
• Molecular Weight: 206.316
• DSSTox Substance ID: DTXSID001253359
• Nikkaji Number: J888.326B
• Mol file: 109053-88-5.mol

Synonyms:SCHEMBL15445431;DTXSID001253359;3-(Phenyldimethylsilyl)acrylic acid;(2E)-3-(Dimethylphenylsilyl)-2-propenoic acid;109053-88-5

Chemical Property of 3-(Phenyldimethylsilyl)acrylic acid

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 206.076306220
• Heavy Atom Count: 14
• Complexity: 227

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C[Si](C)(C=CC(=O)O)C1=CC=CC=C1
• Isomeric SMILES: C[Si](C)(/C=C/C(=O)O)C1=CC=CC=C1

Technology Process of 3-(Phenyldimethylsilyl)acrylic acid

There total 5 articles about 3-(Phenyldimethylsilyl)acrylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

(E)-3-(dimethyl(phenyl)silyl)acrylaldehyde (119480-92-1) → (E)-3-[dimethyl(phenyl)silyl]propenoic acid (109053-88-5)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In water; acetone; for 4h; Ambient temperature;

Reference yield:

ethyl (E)-3-dimethylphenylsilyl-2-propenoate (223245-66-7) → (E)-3-[dimethyl(phenyl)silyl]propenoic acid (109053-88-5)

Guidance literature:

With potassium hydroxide; In methanol; water; at 20 ℃; for 1.5h;

DOI:10.1139/v03-194

Reference yield:

dimethyl(phenyl)silyl lithium (3839-31-4) → (E)-3-[dimethyl(phenyl)silyl]propenoic acid (109053-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 3 h / -78 - -20 °C

1.2: 92 percent / aq. NaHCO₃ / tetrahydrofuran

2.1: LDA / tetrahydrofuran / -78 °C

2.2: MeLi / tetrahydrofuran

3.1: aq. KOH / methanol / 1.5 h / 20 °C

With potassium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol;

DOI:10.1039/b210444j

upstream raw materials:

carbon dioxide

phenyldimethylsilyl chloride

(E)-3-(dimethyl(phenyl)silyl)acrylaldehyde

ethyl (E)-3-dimethylphenylsilyl-2-propenoate

Downstream raw materials:

(E)-3-dimethyl(phenyl)silylpropenoic acid chloride

(S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-3-phenyl-propan-1-one

(Z)-(S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-hex-4-en-1-one

(S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-butan-1-one