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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 | Hazard Symbols | C,F | |
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 |
Conditions | Yield |
---|---|
With sodium hydride; sodium t-butanolate In toluene for 48h; Reflux; | 86% |
With sodium amide In toluene Inert atmosphere; | |
With styrene; sodium |
lithium bis(trimethylsilyl)amide diethyl etherate
sodium hexamethyldisilazane
Conditions | Yield |
---|---|
With sodium t-butanolate In benzene at 20℃; | 77% |
N,N-diphenyl-N'-(trimethylsilyl)hydrazine
A
sodium hexamethyldisilazane
Conditions | Yield |
---|---|
With sodium amide In benzene Heating; | A n/a B 45% |
tetrakis(trimethylsilyl)tetrazene
sodium hexamethyldisilazane
Conditions | Yield |
---|---|
With sodium In diethyl ether at 25℃; for 24h; | 100 % Spectr. |
Conditions | Yield |
---|---|
In tetrahydrofuran Inert atmosphere; Glovebox; |
Conditions | Yield |
---|---|
With N,N-dimethyl-ethanamine; isoprene at 20 - 30℃; Schlenk technique; |
sodium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran-d8 mixed at -78°C (N2); not isolated, detected by NMR; | 100% |
(((C2H5)2O)2Li)Cl2Y(C24H26Si)
sodium hexamethyldisilazane
(((CH3)3Si)2N)Y(C24H26Si)
Conditions | Yield |
---|---|
In toluene Ar-atmosphere; stirring (room temp., overnight); filtering, drying (vac.), crystn. (toluene, -20°C); elem. anal.; | 100% |
sodium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: HN(SiMe3)2; Ar atm.; equimolar ratio, refluxing (2 d); evapn. (dryness, vac.); elem. anal.; | 100% |
15-crown-5
[W(carbonyl)5([bis(trimethylsilyl)methyl]cyanophosphane)]
sodium hexamethyldisilazane
[(OC)5WP(CH(SiMe3)2)CNNa(15-crown-5)]
Conditions | Yield |
---|---|
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% |
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