Sodium bis(trimethylsilyl)amide

Details:

Sodium bis(trimethylsilyl)amide Chemical Properties
Melting point     171-175 °C (lit.)
Boiling point     67°C
density     0.904 g/mL at 25 °C
Fp     43 °F
storage temp.     2-8°C
solubility     Soluble in hexane, toluene, ether,terahydrofuran, benzene and toluene.
form     Liquid
color     Clear orange to brown
Specific Gravity    0.9
Water Solubility     reacts
Sensitive     Moisture Sensitive
Hydrolytic Sensitivity    8: reacts rapidly with moisture, water, protic solvents
BRN     3629917
CAS DataBase Reference    1070-89-9(CAS DataBase Reference)
EPA Substance Registry System    Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, sodium salt (1070-89-9)
Safety Information
Hazard Codes     C,F
Risk 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
RIDADR     UN 3263 8/PG 2
WGK Germany     3
F     10-21
TSCA     Yes
HazardClass     4.3
PackingGroup     III
HS Code     29319090
MSDS Information
Provider    Language
ACROS    English
SigmaAldrich    English
ALFA    English
Sodium bis(trimethylsilyl)amide Usage And Synthesis
Chemical Properties    Slightly yellow to light beige crystalline powder
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.
Uses    It is a strong base; deprotonates ketones and esters to generate enolate derivative.
Uses    Significantly accelerated the polymerization of pheneylacetylene in conjunction with rhodium (I) catalysis
Purification Methods    It can be sublimed at 170o/2mm (bath temperature 220-250o) onto a cold finger, and can be recrystallised from *C6H6 (its solubility is: 10g in 100mL at 60o). It is slightly soluble in Et2O and is decomposed by H2O. [Wannagat & Niederprüm Chem Ber 94 1540 1961.]It is available commercially under N2 in Sure/Seal bottles in tetrahydrofuran (various concentrations) and at ~0.6M in toluene. [Beilstein 4 IV 4014.]
Sodium bis(trimethylsilyl)amide Preparation Products And Raw materials
Raw materials    Tetrahydrofuran-->Sodium-->Toluene-->Hexamethyldisilazane
Preparation Products    TERT-BUTYL 4-FORMYLPYRIDIN-3-YLCARBAMATE-->NONAMETHYLTRISILAZANE