ChemicalBook CAS DataBase List 1070-89-9

1070-89-9

Name	Sodium bis(trimethylsilyl)amide
CAS	1070-89-9
EINECS(EC#)	213-983-8
Molecular Formula	C6H18NNaSi2
MDL Number	MFCD00009835
Molecular Weight	183.37
MOL File	1070-89-9.mol

Synonyms

1,1,1,3,3,3-HEXAMETHYLDISILAZANE SODIUM SALT HEXAMETHYLDISILAZANE SODIUM SALT HMN NA SALT NAHMDS N-SODIOHEXAMETHYLDISILAZANE N-SODIUMHEXAMETHYLDISILAZANE SODIUM BIS(TRIMETHYLSILYL)AMIDE SODIUM HEXAMETHYLDISILAZANE SODIUM HEXAMETHYLDISILAZIDE 1,1,1-trimethyl-n-(trimethylsilyl)-silanaminsodiumsalt sodium-bis-(trimethylsilyl)-amide(solutioninthf) sodiumhexamethyldisilazane,nahmds,in sodiumhexamethyldisilazane,nahmds,intetrahydrofuran SODIUM BIS(TRIMETHYLSILYL)AMIDE SOL., ~2 M IN THF SODIUM BIS(TRIMETHYLSILYL)AMIDE, ~1 M IN THF SODIUM BIS(TRIMETHYLSILYL)AMIDE SOL., ~0 .6 M IN TOLUENE SODIUM BIS(TRIMETHYLSILYL)AMIDE, 1.0M SO LUTION IN TETRAHYDROFURAN SODIUM BIS(TRIMETHYLSILYL)AMIDE, 0.6M SO LUTION IN TOLUENE Sodium bis(trimethylsilyl)amide, 2M solution in THF, pure Sodium bis(trimethylsilyl)amide, pure, 95+%

Chemical Properties

Appearance	Slightly yellow to light beige crystalline powder
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
Hydrolytic Sensitivity	8: reacts rapidly with moisture, water, protic solvents
Sensitive	Moisture Sensitive
Detection Methods	TITR,T
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)
Storage Precautions	Moisture sensitive;Store under nitrogen
EPA Substance Registry System	1070-89-9(EPA Substance)

Safety Data

Hazard Codes	C,F
Risk Statements	R14:Reacts violently with water. R34:Causes burns. R19:May form explosive peroxides. R11:Highly Flammable. R67:Vapors may cause drowsiness and dizziness. R65:Harmful: May cause lung damage if swallowed. R63:Possible risk of harm to the unborn child. R48/20:Harmful: danger of serious damage to health by prolonged exposure through inhalation . R14/15:Reacts violently with water, liberating extremely flammable gases . less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S33:Take precautionary measures against static discharges . S16:Keep away from sources of ignition-No smoking . S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) . S8:Keep container dry . less more
RIDADR	UN 3263 8/PG 2
WGK Germany	3
F	10-21
TSCA	Yes
HazardClass	4.3
PackingGroup	III
HS Code	29319090

Raw materials And Preparation Products

Hazard Information

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

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

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.

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.]

Spectrum Detail

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