Sodium bis(trimethylsilyl)amide

Base Information

• Chemical Name: Sodium bis(trimethylsilyl)amide
• CAS No.: 1070-89-9
• Deprecated CAS: 133766-08-2,42954-57-4,1081831-84-6,1081831-84-6,42954-57-4
• Molecular Formula: C6H19NSi2.Na
• Molecular Weight: 183.376
• Hs Code.: 29319090
• European Community (EC) Number: 213-983-8
• DSSTox Substance ID: DTXSID5061451
• Nikkaji Number: J364.613K
• Wikipedia: Sodium_bis(trimethylsilyl)amide
• Wikidata: Q2742490
• Mol file: 1070-89-9.mol

Synonyms:hexamethyldisilazane;hexamethylsilazane;hexamethylsilazane, aluminum salt;hexamethylsilazane, beryllium salt;hexamethylsilazane, cadmium salt;hexamethylsilazane, cerium (+3) salt;hexamethylsilazane, chromium (3+) salt;hexamethylsilazane, cobalt (2+) salt;hexamethylsilazane, europium (3+) salt;hexamethylsilazane, gadolinium (3+) salt;hexamethylsilazane, gallium salt;hexamethylsilazane, germanium (2+) salt;hexamethylsilazane, holmium (3+) salt;hexamethylsilazane, indium (3+) salt;hexamethylsilazane, iron (3+) salt;hexamethylsilazane, lanthanum (3+) salt;hexamethylsilazane, lead (2+) salt;hexamethylsilazane, lithium salt;hexamethylsilazane, lutetium (3+) salt;hexamethylsilazane, magnesium salt;hexamethylsilazane, manganese (2+) salt;hexamethylsilazane, mercury (2+) salt;hexamethylsilazane, neodymium (3+) salt;hexamethylsilazane, potassium salt;hexamethylsilazane, praseodymium (3+) salt;hexamethylsilazane, samarium (3+) salt;hexamethylsilazane, scandium (3+) salt;hexamethylsilazane, silanamine-(15)N-labeled;hexamethylsilazane, sodium salt;hexamethylsilazane, thallium (3+) salt;hexamethylsilazane, tin (2+) salt;hexamethylsilazane, titanium (3+) salt;hexamethylsilazane, uranium (3+) (3:1) salt;hexamethylsilazane, vanadium (3+) salt;hexamethylsilazane, ytterbium (3+) salt;hexamethylsilazane, yttrium (3+) salt;hexamethylsilazane, zinc salt;N-lithiohexamethyldisilazane;sodium hexamethyldisilazide

Chemical Property of Sodium bis(trimethylsilyl)amide

Chemical Property:

• Appearance/Colour: Slightly yellow to light beige crystalline powder
• Melting Point: 171-175 °C
• Boiling Point: 126 °C at 760 mmHg
• Flash Point: 30 °C
• PSA: 3.24000
• Density: 0.904 g/mL at 25 °C
• LogP: 2.42250
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in hexane, toluene, ether,terahydrofuran, benzene and to
• Water Solubility.: reacts
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 183.08754693
• Heavy Atom Count: 10
• Complexity: 80.9

Purity/Quality:

99% ^*data from raw suppliers

1MSodiumBis(Trimethylsilyl)amideSolutioninTHF ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,F
• Hazard Codes: C,F
• Statements: 14-34-19-11-67-65-63-48/20-14/15-40-37
• Safety Statements: 26-45-62-36/37/39-33-16-43-8

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Silicon)
• Canonical SMILES: C[Si](C)(C)[N-][Si](C)(C)C.[Na+]
• Physical properties: mp 171–175 °C; bp 170 °C/2 mmHg.
• Uses: Sodium bis(trimethylsilyl)amide is a synthetically useful reagent in that it combines both high basicity and nucleophilicity, each of which may be exploited for useful organic transformations such as selective formation of enolates, preparation of Wittig reagents, formation of acyl anion equivalents, and the generation of carbenoid species. As a nucleophile, it has been used as a nitrogen source for the preparation of primary amines.It is useful as a sterically hindered base and as a nucleophile. It is a strong base; deprotonates ketones and esters to generate enolate derivative. Significantly accelerated the polymerization of pheneylacetylene in conjunction with rhodium (I) catalysis

Technology Process of Sodium bis(trimethylsilyl)amide

There total 7 articles about Sodium bis(trimethylsilyl)amide 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: 86.0%

1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → sodium hexamethyldisilazane (1070-89-9)

Guidance literature:

With sodium hydride; sodium t-butanolate; In toluene; for 48h; Reflux;

DOI:10.1016/j.jorganchem.2010.08.019

Reference yield: 77.0%

lithium bis(trimethylsilyl)amide diethyl etherate (18400-61-8) → sodium hexamethyldisilazane (1070-89-9)

Guidance literature:

With sodium t-butanolate; In benzene; at 20 ℃;

DOI:10.1021/acs.organomet.6b00256

Reference yield: 45.0%

N,N-diphenyl-N'-(trimethylsilyl)hydrazine (17938-30-6) → sodium hexamethyldisilazane (1070-89-9) + sodium N',N'-diphenylhydrazide

Guidance literature:

With sodium amide; In benzene; Heating;

DOI:10.1002/cber.19971300806

upstream raw materials:

tetrakis(trimethylsilyl)tetrazene

N,N-diphenyl-N'-(trimethylsilyl)hydrazine

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

hexamethyldisilazan

Downstream raw materials:

diethoxyphosphine

N,O-Bis(trimethylsilyl)trifluoroacetamide

4-Methyl-N-trimethylsilyl-benzophenonimin

N,N'-Dimethyl-N,N'-diphenyl-1,3-bis-trimethylsilanyl-[1,3,2,4]diazadiphosphetidine-2,4-diamine

Refernces

A highly stereoselective addition of the anion derived from α-diazoacetamide to aromatic N-tosylimines

10.1002/anie.200460730

The study focuses on the highly diastereoselective nucleophilic addition of the anion derived from α-diazocarbonyl compounds to aromatic N-tosylimines, a reaction that is significant in organic synthesis. The researchers utilized a variety of chemicals, including α-diazocarbonyl compounds (1a-d) with chiral auxiliaries, N-tosylimines (2a-m), and bases such as lithium diisopropylamide (LDA), sodium hexamethyldisilazide (NaHMDS), and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). They also experimented with additives like LiCl, MgBr2, and HMPA to enhance stereoselectivity. The purpose of these chemicals was to explore the stereocontrol of the reaction, optimize reaction conditions, and synthesize syn- and anti-α-hydroxy-β-amino esters, which are important building blocks in organic chemistry. The study demonstrated that the diastereoselectivity of the reaction could be significantly improved by the use of HMPA, which likely disrupts ion pairing and allows the α-diazocarbonyl anion to react more efficiently. The results have implications for the synthesis of a range of organic compounds, particularly those containing α-hydroxy-β-amino acid derivatives.

The synthesis and characterization of a series of cobalt(II) β-ketoaminato complexes and their cytotoxic activity towards human tumor cell lines

10.1016/j.jinorgbio.2011.03.005

The research focuses on the synthesis, characterization, and evaluation of the cytotoxic activity of a series of cobalt(II) β-ketoaminato complexes towards various human tumor cell lines. The purpose of the study was to investigate the potential of these cobalt compounds as novel cytotoxic drugs, selective towards certain types of tumors. The researchers prepared a series of square planar cobalt(II) compounds with tetradentate β-ketoaminato ligands, varying in the number of ―CF3 ligand substituents, and one tetrahedral cobalt compound with two bidentate ligands. The compounds were synthesized using a multistep reaction sequence involving chemicals such as CoCl2, sodium bis(trimethylsilyl)amide, sodium hydride, tert-butyldimethylchlorosilane, 1,2-diaminoethane, and various β-diketones, including hexafluoroacetylacetone and 4,4,4-trifluoro-1-phenyl-1,3-butanedione. The conclusions drawn from the study indicate that the cobalt complexes, particularly L2Co, exhibit significant cytotoxic activity against prostate cancer and leukemia cells, with activity mediated through mechanisms involving caspase-3, MAP kinases, and reactive oxygen species. These findings suggest that these cobalt complexes could be developed as a new class of cytotoxic drugs.

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