N,N-Bis(trimethylsilyl)formamide

Base Information

• Chemical Name: N,N-Bis(trimethylsilyl)formamide
• CAS No.: 15500-60-4
• Molecular Formula: C7H19NOSi2
• Molecular Weight: 189.405
• Hs Code.: 2931900090
• European Community (EC) Number: 239-530-4
• UNII: FXX3KFS75F
• DSSTox Substance ID: DTXSID8065903
• Nikkaji Number: J317.943E
• Wikidata: Q72447551
• Mol file: 15500-60-4.mol

Synonyms:N,N-Bis(trimethylsilyl)formamide;15500-60-4;Formamide, N,N-bis(trimethylsilyl)-;EINECS 239-530-4;FXX3KFS75F;Bis(trimethylsilyl)formamide;UNII-FXX3KFS75F;C7H19NOSi2;Formamide, 2TMS derivative;SCHEMBL1971956;C7-H19-N-O-Si2;DTXSID8065903;Bis-N,N-(trimethylsilyl)formamide;AKOS006230085;FT-0741355;A809593

Chemical Property of N,N-Bis(trimethylsilyl)formamide

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 4.78mmHg at 25°C
• Melting Point: 158 °C
• Refractive Index: n20/D 1.437
• Boiling Point: 145.8 °C at 760 mmHg
• PKA: 0.16±0.70(Predicted)
• Flash Point: 42 °C
• PSA: 20.31000
• Density: 0.86g/cm³
• LogP: 2.75050
• Solubility.: benzene, CCl4, CH2Cl2, CHCl3.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 189.10051730
• Heavy Atom Count: 11
• Complexity: 132

Purity/Quality:

98%min ^*data from raw suppliers

N,N-BIS(TRIMETHYLSILYL)FORMAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Statements: 10

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)N(C=O)[Si](C)(C)C
• Physical properties: 81–82 °C/20 mmHg; 154 °C/760 mmHg; mp 16–17 °C; n20 D 1.4388.
• Uses: N,N-Bis(trimethylsilyl)formamide can be used as source of nucleophilic formamide and N-silylaldimine synthon. N,N-Bis(trimethylsilyl)formamide (BSF) exists in the amide form with both silyl groups attached to the nitrogen atom. This is in contrast to most other bis(TMS)amides (e.g., bis(TMS)- acetamide), which favor the N,O-bis(TMS)imidate isomer. BSF behaves as an N-formamido nucleophile, reacting with the carbonyl group of aldehydes and activated ketones to give N-formyl-O-trimethylsilyl-N,O-acetals. Similarly, reaction with imines (or their precursors) can in some cases give N-formylN,N-acetals. BSF undergoes reactions with a range of other electrophiles including acid chlorides, chloroformate esters, and isocyanates to give a range of interesting products. When treated with organolithium nucleophiles, attack occurs at the carbonyl function, to provide N-silylaldimines after elimination of a silyloxy unit. Such imines are reported to undergo further reactions to give heterocycles. There are also reports of BSF acting as a silylating agent, to give silyl enol ethers, although it is not commonly used for this application.

Technology Process of N,N-Bis(trimethylsilyl)formamide

There total 4 articles about N,N-Bis(trimethylsilyl)formamide 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: 92.9%

→ N,N-bis(trimethylsilyl)formamide (15500-60-4)

Guidance literature:

Reference yield: 75.0%

chloro-trimethyl-silane (75-77-4) + formamide (77287-34-4,77287-35-5,60100-09-6) → N,N-bis(trimethylsilyl)formamide (15500-60-4)

Guidance literature:

With triethylamine; In benzene; for 1h; Heating;

DOI:10.1039/p19960000883

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → N,N-bis(trimethylsilyl)formamide (15500-60-4)

Guidance literature:

With phenylsilane; C₁₄H₂₄N₄Si*HI; In benzene-d6; at 90 ℃; Inert atmosphere; Schlenk technique;

DOI:10.1021/acscatal.0c03795

upstream raw materials:

chloro-trimethyl-silane

formamide

carbon dioxide

1,1,1,3,3,3-hexamethyl-disilazane

Downstream raw materials:

3,3-dimethyl-4-phenylazetidin-2-one

(E)/(Z)-β-Trimethylsiloxystyrene

1,3-diphenyl-1H-[1,3,5]triazine-2,4-dione

benzyl 6β-[(2,2,2-Trichloroethoxy)carbonylamino]-6α-formamidopenicillanate

Refernces

• 1、 Johnson, A. Peter,Luke, Richard W. A.,Steele, Robert W.,Boa, Andrew N.. "Synthesis of 1-acylamino-1-(trimethylsiloxy)alkanes by trimethylsilyl trifluoromethanesulfonate-catalysed addition of bis(trimethylsilyl)amides to aldehydes". . p. 883 - 893. Retrieved 1996.
• 2、 -. "Method for the preparation of persilylated carboxylic acid amides". . . Retrieved 2008/06/13.