N,O-Bis(trimethylsilyl)acetamide

Base Information

• Chemical Name: N,O-Bis(trimethylsilyl)acetamide
• CAS No.: 10416-59-8
• Molecular Formula: C8H21NOSi2
• Molecular Weight: 203.432
• Hs Code.: 29310095
• European Community (EC) Number: 233-892-7
• UNII: R14N49I64O
• Wikipedia: Bis(trimethylsilyl)acetamide
• Mol file: 10416-59-8.mol

Synonyms:N,O-bis(trimethylsilyl)acetamide

Chemical Property of N,O-Bis(trimethylsilyl)acetamide

Chemical Property:

• Appearance/Colour: Clear to yellowish clear liquid
• Vapor Pressure: 10 hPa (50 °C)
• Melting Point: 24 °C
• Refractive Index: n20/D 1.417(lit.)
• Boiling Point: 162.1 °C at 760 mmHg
• PKA: 5.82±0.50(Predicted)
• Flash Point: 65.5 °C
• PSA: 21.59000
• Density: 0.83 g/cm³
• LogP: 3.09120
• Storage Temp.: 0-6°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with many nonpolar and polar aprotic solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 203.11616736
• Heavy Atom Count: 12
• Complexity: 177

Purity/Quality:

99% ^*data from raw suppliers

N,O-Bis(trimethylsilyl)acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C,Xn,F
• Statements: 10-14-22-34-40-20/21/22-11
• Safety Statements: 26-36/37/39-45-7/8-43A-36-30-23-16-7/9

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Silicon)
• Canonical SMILES: CC(=N[Si](C)(C)C)O[Si](C)(C)C
• Isomeric SMILES: C/C(=N\[Si](C)(C)C)/O[Si](C)(C)C
• Description: Clear to yellowish clear liquid liquid which is soluble in many nonpolar and polar aprotic solvents. The trimethylsilyl group is a frequently utilized monofunctional blocking group for protic organic and inorganic materials. As it eliminated during the silylation is neutral acetamide, N,O-Bis(trimethylsilyl)acetamide can be preferably used for substrates which are acid- or base-sensitive. N,O-bis(trimethylsilyl)-acetamide is an effective silylating agent. It is used in the pharmaceutical and in the chemical industry. Typically the silylating reaction with BSA results in neutral by-products only.
• Uses: Used for blocking and protection of hydroxyl groups in natural products, e.g. amino acids, carbohydrates; Used for blocking and protection of functional groups in organic intermediates; Used for formation of derivatives of H-acid compounds for analysis; The silylated derivatives are volatile and can therefore be determined by gas chromatography. Deblocking is preferably carried out by means of hydrolysis, giving high yields. In some cases, thermal elimination of the trimethylsilyl group is possible. Powerful silylation reagent for a wide range of functional groups under mild conditions N,O-bis(trimethylsilyl)-acetamide (BSA) is frequently used with TMCS as a catalyst to modify a variety of functional groups including carboxyl groups. In one novel application, BSA was used to measure carboxypeptidase activity by forming derivatives which could be determined by gas chromatography.BSA has been used to prepare derivatives of steroids and glucocorticoids. N,O-Bis(trimethylsilyl)acetamide is a powerful silylating agent; reacts with a wide range of functional groups.BSA was used to trimethylsilylate the hydroxyl group of 12 selectively to form in almost quantitative yield (eq 32).The presence of catalytic amounts (～0.02 equiv) of tetrabutylammonium fluoride (TBAF) significantly promoted the silylation of alcohols under mild conditions with high chemoselectivity, i.e., TBAF plays a role as a smooth silyl transfer catalyst from nitrogen to the hydroxyl group.
• Physical properties: bp 71–73°C/35 mmHg.

Technology Process of N,O-Bis(trimethylsilyl)acetamide

There total 8 articles about N,O-Bis(trimethylsilyl)acetamide 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: 93.7%

acetamide (60-35-5) + chloro-trimethyl-silane (75-77-4) → N,O-Bis(trimethylsilyl)acetamide (10416-59-8,132255-83-5)

Guidance literature:

With 1H-imidazole; triethylamine; 2,6-dimethylaniline; at 38 ℃; for 5.25h; under 7.50075 - 165.017 Torr; Temperature; Pressure; Inert atmosphere;

Reference yield: 79.3%

1-(Trimethylsilyl)imidazole (18156-74-6) + N-Trimethylsilylacetamide (13435-12-6) → N,O-bis-(trimethylsilyl)-acetamide (10416-59-8)

Guidance literature:

at 175 ℃; under 75.0075 - 146.265 Torr; 30-theoretical-plates distillation column of Old-ershaw type;

Reference yield:

N-sulphinylacetamide (16767-75-2) + phenylthiotrimethylsilane (4551-15-9) → N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + Hexamethyldisiloxane (107-46-0) + diphenyldisulfane (882-33-7)

Guidance literature:

for 24h; Ambient temperature;

upstream raw materials:

acetamide

chloro-trimethyl-silane

O,O-diethyl S-(trimethylsilyl) phosphorodithioate

N-sulphinylacetamide

Downstream raw materials:

3-Brompropionsaeure-O-trimethylsilylester

trimethylsilyl 6-chloro-1-hexyl ether

6-Chlorohexanoic-acid-O-trimethylsilyl

10-Chlordecanol-O-trimethylsilyl

Refernces

Asymmetric decarboxylative claisen rearrangement reactions of sulfoximine-substituted allylic tosylacetic esters

10.1021/jo050747d

The research explores the development of an asymmetric version of the decarboxylative Claisen rearrangement (dCr) reaction using sulfoximine-substituted allylic acetate esters. The purpose of the study is to achieve high diastereoselectivity in the dCr reaction by introducing chiral sulfoximines as surrogates for sulfones. The researchers synthesized various esters containing N-arylsulfonyl sulfoximines and subjected them to the dCr reaction, achieving diastereoselectivities up to 82:18. Key chemicals used include N-(2,4,6-triisopropylphenylsulfonyl)-S-phenyl sulfoximine, which provided the best selectivity, and reagents like N,O-bis(trimethylsilyl)acetamide (BSA) and potassium acetate (KOAc) for facilitating the reaction. The study concludes that the stereochemical outcome of the rearrangement can be rationalized by a pseudochair transition-state model, with the stereochemistry of the major isomers confirmed by X-ray crystallography. The results suggest that further modifications to the system, such as adding more electron-withdrawing groups, could enhance selectivity and lower reaction temperatures.

The adenine derivative of α-L-LNA (α-L-ribo configured locked nucleic acid): Synthesis and high-affinity hybridization towards DNA, RNA, LNA and α-L-LNA complementary sequences

10.1016/S0960-894X(01)00110-X

The research focuses on the synthesis and hybridization properties of a 9-mer adenine derivative of α-L-LNA (α-L-ribo configured locked nucleic acid), which is a type of nucleic acid mimic designed to have superior properties such as increased stability towards nucleolytic degradation and enhanced binding affinity and specificity towards complementary nucleic acid targets. The study successfully developed a synthetic route for the first α-L-LNA purine monomer, involving the synthesis of a bicyclic adenine nucleoside through a condensation reaction between l-threo-pentofuranose derivative and 6-N-benzoyladenine, followed by C20-epimerization and cyclization. The synthesized α-L-LNA monomers were then incorporated into a 9-mer oligonucleotide, which demonstrated high-affinity hybridization with complementary DNA, RNA, LNA, and α-L-LNA target sequences. The chemicals used in the process included 6-N-benzoyladenine, SnCl4, TMS-triflate, N,O-bis(trimethylsilyl)acetamide, mesyl chloride, sodium hydride, and various other reagents for protection, deprotection, and purification steps. The conclusions of the research were that the α-L-LNA monomers, particularly the adenine derivatives, significantly enhance the affinity of the resulting oligonucleotides for their complementary sequences, and that α-L-LNA:α-L-LNA and α-L-LNA:LNA duplexes form exceptionally stable structures, comparable to LNA:LNA duplexes.

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