((Trimethylsilyl)methyl)boronic acid

Base Information

• Chemical Name: ((Trimethylsilyl)methyl)boronic acid
• CAS No.: 74213-41-5
• Molecular Formula: C4H13BO2Si
• Molecular Weight: 132.043
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID50463621
• Nikkaji Number: J1.593.769F
• Wikidata: Q82288596
• Mol file: 74213-41-5.mol

Synonyms:((Trimethylsilyl)methyl)boronic acid;74213-41-5;Trimethylsilylmethylboronic Acid;[(trimethylsilyl)methyl]boronic acid;Boronic acid, [(trimethylsilyl)methyl]-;SCHEMBL1452239;DTXSID50463621;((Trimethylsilyl)methyl)boronicacid;EN300-6225962

Chemical Property of ((Trimethylsilyl)methyl)boronic acid

Chemical Property:

• PSA: 40.46000
• LogP: 0.33660
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 132.0777864
• Heavy Atom Count: 8
• Complexity: 68.9

Purity/Quality:

99% ^*data from raw suppliers

((Trimethylsilyl)methyl)boronic acid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C[Si](C)(C)C)(O)O

Technology Process of ((Trimethylsilyl)methyl)boronic acid

There total 3 articles about ((Trimethylsilyl)methyl)boronic 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: 75.0%

Trimethyl borate (121-43-7,63156-11-6) + (tri-methylsilyl)methylmagnesium chloride → ((trimethylsilyl)methyl)boronic acid (74213-41-5)

Guidance literature:

In diethyl ether; stirred at -78°C; aequeous work-up;

DOI:10.1039/c39800000039

Reference yield:

water (7732-18-5) + potassium (trimethylsilyl)methyltrifluoroborate → ((trimethylsilyl)methyl)boronic acid (74213-41-5)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; In chlorobenzene; at 100 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jacs.0c11964

Reference yield:

Trimethyl borate (121-43-7,63156-11-6) + Chloromethyltrimethylsilane (2344-80-1) → ((trimethylsilyl)methyl)boronic acid (74213-41-5)

Guidance literature:

With magnesium; In diethyl ether; Me3SiCH2MgCl was prepd. as in F.C.Whitmore et al., J.Am.Chem.Soc.1946,68,481 or D.Peterson, J.Org.Chem.1968, 33, 780, added simultaneously dropwise with B(OMe)3 in Et2O under Ar to Et2O at -78°C, stirred for 2-3 h, warmed to room temp. overnight; reaction mixt. was treated with ice-cold 2 M HCl, extd. with 5:1 Et2O-CH2Cl2, ext. was evapd. residue recrystd. from water; not characterized;

DOI:10.1021/om00074a005

upstream raw materials:

Trimethyl borate

Chloromethyltrimethylsilane

water

Downstream raw materials:

1-{4-[(trimethylsilyl)methyl]phenyl}ethan-1-one

Refernces

• 1、 Matteson, Donald S.,Majumdar, Debesh. "Deprotonation of a Trimethylsilylmethaneboronic Ester". . p. 39 - 40. Retrieved 2007/10/02.