Sodium bis(trimethylsilyl)amide Chemical Properties

Melting point:

171-175 °C (lit.)

Boiling point:

67°C

Density 

0.904 g/mL at 25 °C

Flash point:

43 °F

storage temp. 

2-8°C

solubility 

Soluble in hexane, toluene, ether,terahydrofuran, benzene and toluene.

form 

Liquid

Specific Gravity

0.9

color 

Clear orange to brown

Water Solubility 

reacts

Sensitive 

Moisture Sensitive

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

BRN 

3629917

Exposure limits

ACGIH: TWA 50 ppm; STEL 100 ppm (Skin)
OSHA: TWA 200 ppm(590 mg/m3)
NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)

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

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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

It is a strong base; deprotonates ketones and esters to generate enolate derivative.

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

Significantly accelerated the polymerization of pheneylacetylene in conjunction with rhodium (I) catalysis

General Description

Sodium bis(trimethylsilyl)amide solution (NaHMDS) is widely used as a strong base in organic synthesis for deprotonation reactions and base-catalyzed reactions. It is also involved in the generation of enolates, Wittig reagents and carbenes.

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(1070-89-9)Related Product Information

• Release agent No.8
• Methanesiliconic acid sodium salt
• Sodium amide
• Hexamethyldisilazane
• Fomesafen
• N-(Trimethylsilyl)acetamide
• Lithium bis(trimethylsilyl)amide
• RINK AMIDE RESIN
• Trimethylsilylacetylene
• Sodium hydroxide
• Rink Amide Linker
• Sodium benzoate
• Sodium acetate
• Sodium bicarbonate
• Hexamethyldisiloxane
• Bis(triphenylphosphinepalladium) acetate
• Potassium bis(trimethylsilyl)amide
• Bis(triphenylphosphine)nickel(II)chloride