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:

(1S,4aS,10aR)-6-(benzyloxy)-N-((1S,4aS,10aR)-6-(benzyloxy)-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carbonyl)-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxamide

2-Methyl-7-(2-methyl-4,5-diphenyl-imidazol-1-yl)-heptanoic acid ethyl ester

3-(tert-butyloxycarbonylamino)-4-methyl-pyridine

4-Benzyloxy-7-(4-chloro-phenylsulfanyl)-3-methoxybicyclo [4.2.0]octa-1,3,5-triene-7-carbonitrile

Refernces

• 1、 Knizek, Joerg. "Synthesis and structures of sodium phenylhydrazides". . p. 1053 - 1062. Retrieved 1997.
• 2、 Zou, Jin,Berg, David J.,Oliver, Allen,Twamley, Brendan. "Unusual redox chemistry of ytterbium carbazole-bis(oxazoline) compounds: Oxidative coupling of primary phosphines by an ytterbium carbazole- bis(oxazoline) dialkyl". . p. 6532 - 6540. Retrieved 2013.
• 3、 Chiu, Hsin-Chun,Pearce, Adam J.,Dunn, Peter L.,Cramer, Christopher J.,Tonks, Ian A.. "β-Oxo-δ-diimine Nickel Complexes: A Comparison of Tautomeric Active Species in Ethylene Polymerization Catalysis". . p. 2076 - 2085. Retrieved 2016.
• 4、 Mansell, Stephen M.,Arnold, Polly L.. "Coordination of isocyanide and reduction of cyclooctatetraene by a homoleptic uranium(III) aryloxide, and characterisation of the heteroleptic uranium(III) dimer [{U(N″)2(thf)(μ-I)}2]". . p. 82 - 87. Retrieved 2016.
• 5、 Collum, David B.,Woltornist, Ryan A.. "Ketone Enolization with Sodium Hexamethyldisilazide: Solvent- And Substrate-Dependent E- Z Selectivity and Affiliated Mechanisms". . p. 17452 - 17464. Retrieved 2021/11/04.