Sodium bis(trimethylsilyl)amide supplier

Name
Sodium bis(trimethylsilyl)amide
EINECS 213-983-8
CAS No. 1070-89-9
Article Data16
CAS DataBase
Density 0.904 g/mL at 25 °C
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;
PSA 3.24000
LogP 2.42250

Synthetic route

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 1070-89-9
sodium hexamethyldisilazane

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium amide In benzene Heating;	A n/a B 45%

: 52764-24-6
tetrakis(trimethylsilyl)tetrazene

: 1070-89-9
sodium hexamethyldisilazane

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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%

...Expand

: C14H25B9N2

: 1070-89-9
sodium hexamethyldisilazane

: C14H24B9N2(1-)*Na(1+)

Conditions

Conditions	Yield
In tetrahydrofuran at -30℃; for 0.25h; Inert atmosphere;	100%

: 1246185-31-8
2-(N,N-dimethylaminomethyl)-1,1'-bis(phosphanyl)ferrocene

: 1070-89-9
sodium hexamethyldisilazane

: (C5H4(PHNa))Fe(C5H3(PHNa)CH2NMe2)

Conditions

Conditions	Yield
In hexane; toluene addn. of soln. of Si compd. (2 equiv.) in toluene to soln. of Fe complexin hexane at -78°C, stirring within few minutes; isolation of solid;	99%

: 1070-89-9
sodium hexamethyldisilazane

: 100-47-0
benzonitrile

: 129454-37-1
natrium-N,N'-bis(trimethylsilyl)benzamidinat

Conditions

Conditions	Yield
With diethyl ether for 24h; Ambient temperature;	98%

: tris(bis(trimethylsilyl)amido)samarium(III)

: 1070-89-9
sodium hexamethyldisilazane

: 536-74-3
phenylacetylene

: [Na(C4H8O)Sm(N(Si(CH3)3)2)3(CCC6H5)]

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: NH(SiMe3)2; dry atm.; molar ratio 1:1:1, stirring (-78°C, 2 h), warming (roomtemp.); evapn. (vac.); elem. anal.;	98%

...Expand

: C50H54Ir2N7

: 1070-89-9
sodium hexamethyldisilazane

: C50H54Ir2N7(1-)*Na(1+)

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;	98%

: 185699-79-0
(C5H5)Fe(C5H4C(NC6H11)(NHC6H11))

: 1070-89-9
sodium hexamethyldisilazane

: Na(1+)*C5H5FeC5H4C(NC6H11)2(1-)=C5H5FeC5H4C(NC6H11)2Na

Conditions

Conditions	Yield
In hexane a suspn. in hexane was stirred overnight (inert atm.); filtered, dried under reduced pressure;	97%

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

: 1070-89-9
sodium hexamethyldisilazane

: 122-39-4
diphenylamine

: [(C4H8O)2Na((C6H5)2N)2Yb(N(Si(CH3)3)2)2]

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: LiCl, NH(SiMe3)2; Ar atm.; molar ratio Yb salt:Na salt:HNPh2 1:1:2, stirring; evapn. (after 6 h, vac. (2 h, 1E-4 torr)); elem. anal.;	97%

...Expand

: tris[N,N-bis(trimethylsilyl)amide]gadolinium(III)

: 1070-89-9
sodium hexamethyldisilazane

: 122-39-4
diphenylamine

: [(C4H8O)2Na((C6H5)2N)2Gd(N(Si(CH3)3)2)2]

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: LiCl, NH(SiMe3)2; Ar atm.; molar ratio Gd salt:Na salt:HNPh2 1:1:2, stirring; evapn. (after 6 h, vac. (2 h, 1E-4 torr)); elem. anal.;	97%

...Expand

: Lu(N(SiMe3)2)3

: 1070-89-9
sodium hexamethyldisilazane

: [(C4H8O)3NaCH2Lu(N(Si(CH3)3)2)2N(Si(CH3)3)Si(CH3)2]

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: HN(SiMe3)2; Ar atm.; equimolar ratio, refluxing (2 d); evapn. (dryness, vac.); elem. anal.;	97%

: 1048698-05-0
4-methyl-1,2,3,5-tetraphenyl-1,2-diaza-3,5-diborolidine

: 1070-89-9
sodium hexamethyldisilazane

: 1048638-05-6
4-methyl-1,2,3,5-tetraphenyl-1,2-diaza-3,5-diborolyl sodium

Conditions

Conditions	Yield
In tetrahydrofuran under Ar; soln. of B compd. in THF added to stirred soln. of NaN(SiMe3)2in THF; stirred at ambient temp. for 3 h; volatiles removed under vac.; washed with hexane; dried under vac.;	97%

: 109-99-9
tetrahydrofuran

: 862887-61-4
titanium(IV)(N(tert-Bu)(3,5-Me2C6H3))3 formate

: 1070-89-9
sodium hexamethyldisilazane

: C36H54N3OTi(1-)*Na(1+)*C4H8O

Conditions

Conditions	Yield
at 20℃; for 1h; Inert atmosphere; Glovebox; Cooling;	97%

...Expand

: tris(bis(trimethylsilyl)amido)samarium(III)

: 1070-89-9
sodium hexamethyldisilazane

: 122-39-4
diphenylamine

: [(C4H8O)2Na((C6H5)2N)2Sm(N(Si(CH3)3)2)2]

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: HN(SiMe3)2; Ar atm.; 2 equiv. of HNPh2, stirring (0°C); evapn. (after 2 h, vac.); elem. anal.;	96%

...Expand

: 10043-11-5
ammonia borane complex

: 1070-89-9
sodium hexamethyldisilazane

: 1452577-09-1
B3H12N2(1-)*Na(1+)

Conditions

Conditions	Yield
In fluorobenzene; toluene at 50℃; for 24h; Inert atmosphere;	96%

: 1722-33-4
methylamine-borane

: 1070-89-9
sodium hexamethyldisilazane

: 1452577-10-4
C2H16B3N2(1-)*Na(1+)

Conditions

Conditions	Yield
In fluorobenzene; toluene at 60℃; for 24h; Inert atmosphere; Glovebox;	96%

: 1070-89-9
sodium hexamethyldisilazane

: 131968-42-8
2-{1-[1-Chloro-meth-(E)-ylidene]-2,2-dimethyl-propylsulfanyl}-isoindole-1,3-dione

: 144216-67-1
N-(1-tert-butyl-2-chlorovinylthio)bis(trimethylsilyl)amine

Conditions

Conditions	Yield
In tetrahydrofuran 1.) -78 deg C, 15 min, 2.) -78 deg C to room temperature;	95%

: ytterbium(II) iodide

: 1070-89-9
sodium hexamethyldisilazane

: (Yb(NSiMe3)(μ-SiMe3))2

Conditions

Conditions	Yield
In diethyl ether absence of air and moisture; addn. of 2 equiv. of ligand to YbI2 (0°C), stirring (1 h), warming to room temp., stirring (16 h, pptn.), filtration, solvent removal from filtrate (vac.); drying (20°C, 1E-2 Torr, 2 days);	95%

: 1070-89-9
sodium hexamethyldisilazane

: tris(bis(trimethylsilyl)amido)europium(III)

: 536-74-3
phenylacetylene

: [Na(C4H8O)Eu(N(Si(CH3)3)2)3(CCC6H5)]

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: NH(SiMe3)2; dry atm.; molar ratio 1:1:1, stirring (-78°C, 2 h), warming (roomtemp.); evapn. (vac.); elem. anal.;	95%

...Expand

: 41836-21-9
tris(bis(trimethylsilylamido))cerium(III)

: 1070-89-9
sodium hexamethyldisilazane

: 536-74-3
phenylacetylene

: [Na(C4H8O)Ce(N(Si(CH3)3)2)3(CCC6H5)]

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: NH(SiMe3)2; dry atm.; molar ratio 1:1:1, stirring (-78°C, 2 h), warming (roomtemp.); evapn. (vac.); elem. anal.;	95%

...Expand

: 1070-89-9
sodium hexamethyldisilazane

: tris(bistrimethylsilylamine)scandium(III)

: [(C4H8O)3NaCH2Sc(N(Si(CH3)3)2)2N(Si(CH3)3)Si(CH3)2]

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: HN(SiMe3)2; Ar atm.; equimolar ratio, refluxing (2 d); evapn. (dryness, vac.); elem. anal.;	95%

: 1070-89-9
sodium hexamethyldisilazane

: tris(bistrimethylsilylamine)scandium(III)

: 122-39-4
diphenylamine

: Na(1+)*Sc(3+)*2C4H8O*2(C6H5)2N(1-)*2((CH3)3Si)2N(1-)=[(C4H8O)2Na((C6H5)2N)2Sc(N(Si(CH3)3)2)2]

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: LiCl, NH(SiMe3)2; Ar atm.; molar ratio Sc salt:Na salt:HNPh2 1:1:2, stirring; evapn. (after 6 h, vac. (2 h, 1E-4 torr)); elem. anal.;	95%

...Expand

: 109-99-9
tetrahydrofuran

: 88-18-6
2-tert-Butylphenol

: 1070-89-9
sodium hexamethyldisilazane

: [(THF)Na(μ3-o-tert-butylphenol)]4*THF

Conditions

Conditions	Yield
for 12h; Glovebox; Inert atmosphere;	94.4%

...Expand

: 28240-68-8
methylenebis(dichlorophosphine)

: 1070-89-9
sodium hexamethyldisilazane

: 78463-59-9
C19H55N3P2Si6

Conditions

Conditions	Yield
In diethyl ether	94%

: 1070-89-9
sodium hexamethyldisilazane

: CH2(P(Cl)(N(Si(CH3)3)2))2

: 78463-59-9
C19H55N3P2Si6

Conditions

Conditions	Yield
In diethyl ether	94%

: 2720-03-8
bis(pentafluorophenyl)boron chloride

: 1070-89-9
sodium hexamethyldisilazane

: 201163-50-0
N-(bis(perfluorophenyl)boraneyl)-1,1,1-trimethyl-N-(trimethylsilyl)silanamine

Conditions

Conditions	Yield
In toluene byproducts: NaCl; N2-atmosphere; stirring (room temp., 30 min); evapn., extg. (pentane), crystn. on concg. (5°C); elem. anal.;	94%

: bis(bis(trimethylsilyl)amido)zinc(II)

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: 1070-89-9
sodium hexamethyldisilazane

: [Na((CH2CH2O)4)2](1+)*[Zn(N(Si(CH3)3)2)3](1-)=[Na((CH2CH2O)4)2][Zn(N(Si(CH3)3)2)3]

Conditions

Conditions	Yield
In toluene Ar atm.; stirring (20°C, 5 min+2 d); filtn., washing (n-hexane), drying (vac.); elem. anal.;	94%

...Expand

: tBuIr2N

: 1070-89-9
sodium hexamethyldisilazane

: tBuIr2N-Na+

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;	94%

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

Product Name

Sodium bis(trimethylsilyl)amide

Synthetic route

Sodium bis(trimethylsilyl)amide Specification

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