trimethylsilyl 2,2,2-trifluoro-N-(trimethylsilyl)ethanecarboximidate

Base Information

• Chemical Name: trimethylsilyl 2,2,2-trifluoro-N-(trimethylsilyl)ethanecarboximidate
• CAS No.: 25561-30-2
• Molecular Formula: C8H18F3NOSi2
• Molecular Weight: 257.403
• Hs Code.: 29310095
• European Community (EC) Number: 247-103-9
• Wikipedia: BSTFA
• Mol file: 25561-30-2.mol

Synonyms:N,O-bis(TMS)3FAN;N,O-bis(trimethylsilyl)trifluoroacetamide

Chemical Property of trimethylsilyl 2,2,2-trifluoro-N-(trimethylsilyl)ethanecarboximidate

Chemical Property:

• Appearance/Colour: Clear to yellowish clear liquid
• Vapor Pressure: 0.193mmHg at 25°C
• Melting Point: -10°C
• Refractive Index: n20/D 1.384(lit.)
• Boiling Point: 155 °C at 760 mmHg
• PKA: 1.82±0.50(Predicted)
• Flash Point: 23.9 °C
• PSA: 21.59000
• Density: 0.99 g/cm³
• LogP: 3.63360
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with chloroform.
• Water Solubility.: hydrolyses
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 257.08790175
• Heavy Atom Count: 15
• Complexity: 250

Purity/Quality:

98% min ^*data from raw suppliers

N,O-Bis(trimethylsilyl)trifluoroacetamide(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, C, F
• Hazard Codes: C,F,T
• Statements: 11-34-10-35-14
• Safety Statements: 26-36/37/39-45-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Silicon)
• Canonical SMILES: C[Si](C)(C)N=C(C(F)(F)F)O[Si](C)(C)C
• Isomeric SMILES: C[Si](C)(C)/N=C(/C(F)(F)F)\O[Si](C)(C)C
• Uses: Used for synthesis of pharmaceutical intermediates. Used as a reactant in the preparation of pyrimidinone ribosides and analogs that show anti-tumor properties. N,O-bis(trimethylsilyl)-trifluoroacetamide (BSTFA) is similar to BSA in specificity of modification and there are several studies which have used both reagents.One study found BSTFA superior to BSA in product stability and yield of derivative. Another study compared several trimethylsilyl donors for end-capping of silica and observed that BSTFA was more reactive than BSA but less reactive than TMCim. Both BSA and BSTFA were used to prepare trimethylsilyl derivatives of pyrimidines and purines.Current work has used BSTFA for metabolomics analysis of urine,for the measurement of khatamines (psychoactive amines of khat (Catha edulis Forsk), and for the measurement of acrylamide in cocoa. N,O-Bis(trimethylsilyl)trifluoroacetamide is used for analytical purposes or as a chemical reagent for synthesis of more complex molecules. It is silylation reagent useful in GC and GC-MS for the derivatization of a wide range of functional groups under mild conditions. It is also used as DAT inhibitor and a SLC6A2 inhibitor. It is routinely used to derivatize carboxylic acids, phenols, steroids, amines, alcohols, and alkaloids and amides.

Technology Process of trimethylsilyl 2,2,2-trifluoro-N-(trimethylsilyl)ethanecarboximidate

There total 4 articles about trimethylsilyl 2,2,2-trifluoro-N-(trimethylsilyl)ethanecarboximidate 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:

chloro-trimethyl-silane (75-77-4) + 2,2,2-trifluoroacetamide (354-38-1) → N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2)

Guidance literature:

With triethylamine;

Reference yield:

trifluoracetyl chloride (354-32-5) + sodium hexamethyldisilazane (1070-89-9) → N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2)

Guidance literature:

Reference yield:

→ N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2)

Guidance literature:

upstream raw materials:

trifluoracetyl chloride

sodium hexamethyldisilazane

chloro-trimethyl-silane

2,2,2-trifluoroacetamide

Downstream raw materials:

Dimethoxymethane

Bis-trimethylsilanyloxy-methane

(E)-3-(3-Methoxy-4-trimethylsilanyloxy-phenyl)-acrylic acid

Refernces

Synthesis of 7α methoxy 7 [2 (substituted thio)acetamido]cephalosporin derivatives and their antibacterial activities

10.1248/cpb.24.2629

The research focused on the synthesis and antibacterial activities of 7a-methoxy-7-[2-(substituted thio)acetamido]cephalosporin derivatives. The purpose was to develop more active cephalosporin derivatives by nucleophilic displacement of the halogen atom of 7β-(2-halogenoacetamido)-7-methoxy cephalosporanic acid derivatives with various mercapto compounds. The study concluded that the synthesized compounds, particularly those with a five-membered heterocyclic ring in the acylamido group, exhibited potent antibacterial activities, with compound (6) showing activities comparable to the semi-synthetic antibiotic cefoxitin and superior to cephalothin against gram-negative bacteria. Key chemicals used in the process included cephamycin C, tert-butoxycarbonyl azide, diphenyldiazomethane, chloroacetyl chloride, bis(trimethylsilyl)trifluoroacetamide, and various mercapto compounds for the nucleophilic displacement reaction.