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Sodium bis(trimethylsilyl)amide

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Name

Sodium bis(trimethylsilyl)amide

EINECS 213-983-8
CAS No. 1070-89-9 Density 0.904 g/mL at 25 °C
PSA 3.24000 LogP 2.42250
Solubility reacts with water Melting Point 171-175 °C
Formula C6H19NSi2.Na Boiling Point 126 °C at 760 mmHg
Molecular Weight 183.376 Flash Point 30 °C
Transport Information UN 3263 8/PG 2 Appearance Slightly yellow to light beige crystalline powder
Safety 26-45-62-36/37/39-33-16-43-8 Risk Codes 34-19-11-67-65-63-48/20-14/15
Molecular Structure Molecular Structure of 1070-89-9 (Sodium bis(trimethylsilyl)amide) Hazard Symbols CorrosiveC,FlammableF
Synonyms

Disilazane,1,1,1,3,3,3-hexamethyl-, sodium deriv. (6CI);Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-,sodium salt (8CI,9CI);Sodium, [bis(trimethylsilyl)amino]- (7CI);1,1,1,3,3,3-Hexamethyldisilazane sodium salt;Bis(trimethylsilyl)amine sodiumsalt;Hexamethyldisilazane sodium salt;Hexamethyldisilazylsodium;N,N-Bis(trimethylsilyl)amine sodium salt;N-Sodiohexamethyldisilazane;Sodiobis(trimethylsilyl)amine;Sodium N,N-bis(trimethylsilyl)amide;Sodiumbis(trimethylsilyl)amide;Sodiumbis(trimethylsilyl)amine;Sodium hexamethyldisilazane;Sodium hexamethyldisilazide;Sodium hexamethyldisilylamide;

Article Data 16

Sodium bis(trimethylsilyl)amide Synthetic route

999-97-3

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

1070-89-9

sodium hexamethyldisilazane

Conditions
ConditionsYield
With sodium hydride; sodium t-butanolate In toluene for 48h; Reflux;86%
With sodium amide In toluene Inert atmosphere;
With styrene; sodium
18400-61-8

lithium bis(trimethylsilyl)amide diethyl etherate

1070-89-9

sodium hexamethyldisilazane

Conditions
ConditionsYield
With sodium t-butanolate In benzene at 20℃;77%
17938-30-6

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

A

1070-89-9

sodium hexamethyldisilazane

B

sodium N',N'-diphenylhydrazide

Conditions
ConditionsYield
With sodium amide In benzene Heating;A n/a
B 45%
52764-24-6

tetrakis(trimethylsilyl)tetrazene

1070-89-9

sodium hexamethyldisilazane

Conditions
ConditionsYield
With sodium In diethyl ether at 25℃; for 24h;100 % Spectr.
72525-60-1

hexamethyldisilazan

7646-69-7

sodium hydride

1070-89-9

sodium hexamethyldisilazane

Conditions
ConditionsYield
In tetrahydrofuran Inert atmosphere; Glovebox;
7440-23-5

sodium

999-97-3

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

1070-89-9

sodium hexamethyldisilazane

Conditions
ConditionsYield
With N,N-dimethyl-ethanamine; isoprene at 20 - 30℃; Schlenk technique;

Mo(hydridotris(3,5-dimethylpyrazolyl)borate)(CO)2(C2H3)

1070-89-9

sodium hexamethyldisilazane

Na{(hydrotris(3,5-dimethylpyrazolyl)borate)(CO)2Mo=C=CH2}

Conditions
ConditionsYield
In tetrahydrofuran-d8 mixed at -78°C (N2); not isolated, detected by NMR;100%
253305-31-6

(((C2H5)2O)2Li)Cl2Y(C24H26Si)

1070-89-9

sodium hexamethyldisilazane

253305-32-7

(((CH3)3Si)2N)Y(C24H26Si)

Conditions
ConditionsYield
In toluene Ar-atmosphere; stirring (room temp., overnight); filtering, drying (vac.), crystn. (toluene, -20°C); elem. anal.;100%

tris(bis(trimethylsilyl)amido)ytterbium(III)

1070-89-9

sodium hexamethyldisilazane

[(C4H8O)3NaCH2Yb(N(Si(CH3)3)2)2N(Si(CH3)3)Si(CH3)2]

Conditions
ConditionsYield
In tetrahydrofuran byproducts: HN(SiMe3)2; Ar atm.; equimolar ratio, refluxing (2 d); evapn. (dryness, vac.); elem. anal.;100%
33100-27-5

15-crown-5

851576-85-7

[W(carbonyl)5([bis(trimethylsilyl)methyl]cyanophosphane)]

1070-89-9

sodium hexamethyldisilazane

947333-62-2

[(OC)5WP(CH(SiMe3)2)CNNa(15-crown-5)]

Conditions
ConditionsYield
In tetrahydrofuran under Ar; cooled (-80°C) soln. of NaN(SiMe3)2 in THF added dropwise to stirred soln. of W complex in THF and 15-crown-5; warmed slowly toroom temp. for 3.5 h; solvent removed under vac.; washed with Et2O and n-pentane; dried under reduced pressure; elem. anal.;100%

Sodium bis(trimethylsilyl)amide Specification

The IUPAC name of this chemical is Sodium bis(trimethylsilyl)amide. With the CAS registry number 1070-89-9 and EINECS registry number 213-983-8, it is also named as N,N-bis(trimethylsilyl)amine sodium salt. In addition, the molecular formula is C6H19NSi2.Na. It is a strong base used for deprotonation reactions or base catalyzed reaction. And its advantages are that it is available as a solid and it is soluble in a wide range of nonpolar solvents.

Physical properties about this chemical are: (1)ACD/LogP: 2.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.78; (4)ACD/LogD (pH 7.4): -0.78; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 12.03 Å2; (13)Flash Point: 30 °C; (14)Enthalpy of Vaporization: 36.38 kJ/mol; (15)Boiling Point: 126 °C at 760 mmHg; (16)Vapour Pressure: 11.9 mmHg at 25°C.

Uses of Sodium bis(trimethylsilyl)amide: it is widely used as a base for C-H acids and N-H acids. And it reacts with alkyl halides to give amine derivatives: (CH3)3Si)2NNa + RBr → (CH3)3Si)2NR + NaBr; (CH3)3Si)2NR + H2O → (CH3)3Si)2O + RNH2. This method has been extended to aminomethylation via the reagent (CH3)3Si)2NCH2OMe.

When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable and can cause burns. It can react violently with water and liberate extremely flammable gases. And it may form explosive peroxides. In addition, it may has risk of harm to the unborn child and may cause lung damage if swallowed. Moreover, it may cause drowsiness and dizziness. Before using it, you should keep container dry. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show label where possible). In addition, 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). What's more, you should keep away from sources of ignition and no smoking. And you can take precautionary measures against static discharges.

You can still convert the following datas into molecular structure:
(1)SMILES: [Na+].[N-]([Si](C)(C)C)[Si](C)(C)C
(2)InChI: InChI=1/C6H18NSi2.Na/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1
(3)InChIKey: WRIKHQLVHPKCJU-UHFFFAOYAO

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