Product Name

  • Name

    Lithium bis(trimethylsilyl)amide

  • EINECS 223-725-6
  • CAS No. 4039-32-1
  • Article Data82
  • CAS DataBase
  • Density 0.891 g/mL at 25 °C
  • Solubility hydrolysis with water
  • Melting Point 73 °C
  • Formula C6H18LiNSi2
  • Boiling Point 126 °C at 760 mmHg
  • Molecular Weight 167.328
  • Flash Point 30 °C
  • Transport Information UN 2925 4.1/PG 2
  • Appearance light yellow to yellow crystalline powder
  • Safety 9-16-26-29-33-36/37/39-45-61-62-57-43
  • Risk Codes 11-34-48/20-63-65-67-51/53-35-62-14
  • Molecular Structure Molecular Structure of 4039-32-1 (Lithium bis(trimethylsilyl)amide)
  • Hazard Symbols FlammableF, CorrosiveC, DangerousN
  • Synonyms Disilazane, 1,1,1,3,3,3-hexamethyl-,lithium salt (8CI);Lithium, [bis(trimethylsilyl)amino]- (7CI);Silanamine,1,1,1-trimethyl-N-(trimethylsilyl)-, lithium salt (9CI);(Hexamethyldisilazane)lithium;1,1,1-Trimethyl-N-(trimethylsilyl)silanamine lithium salt;Bis(trimethylsilyl)amidolithium;Hexamethyldisilazane lithium salt;Lithiohexamethyldisilazane;Lithiumhexamethyldisilazanate;Lithium hexamethyldisilazane;Lithiumhexamethyldisilazanide;N,N-Bis(trimethylsilyl)amine lithium salt;N-Lithiohexamethyldisilazane;[1,1,1-Trimethyl-N-(trimethylsilyl)silanaminato]lithium;
  • PSA 3.24000
  • LogP 2.42250

Synthetic route

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

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

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
With n-butyllithium In hexane at 20℃; Inert atmosphere;99.5%
With lithium at -20℃; for 16h; Time; Temperature;99.5%
With n-butyllithium In hexane at 20℃; for 24h; Inert atmosphere; Schlenk technique;92%
lithium bis(trimethylsilyl)amide diethyl etherate
18400-61-8

lithium bis(trimethylsilyl)amide diethyl etherate

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

N,N,N'-tris(trimethylsilyl)phosphenimidous amide
50732-21-3, 65428-75-3

N,N,N'-tris(trimethylsilyl)phosphenimidous amide

2,2,6,6-tetramethylpiperidinyl-lithium
38227-87-1

2,2,6,6-tetramethylpiperidinyl-lithium

A

N-trimethylsilylimidophosphenous acid 2,2,6,6-tetramethylpiperidine
72821-01-3

N-trimethylsilylimidophosphenous acid 2,2,6,6-tetramethylpiperidine

B

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In tetrahydrofuran at 40℃; for 3h;A 4.6 g
B n/a
tetrakis(trimethylsilyl)tetrazene
52764-24-6

tetrakis(trimethylsilyl)tetrazene

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
With lithium In diethyl ether at 36℃; for 72h;20 % Spectr.
Lithium-bis(trimethylsilyl)tetrazenid
79345-33-8, 79345-34-9

Lithium-bis(trimethylsilyl)tetrazenid

A

N,N'-bis(trimethylsilyl)hydrazine
692-56-8

N,N'-bis(trimethylsilyl)hydrazine

B

Dilithium-bis(trimethylsilyl)tetrazenid
79345-33-8, 79345-34-9

Dilithium-bis(trimethylsilyl)tetrazenid

C

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In diethyl ether at 70℃; for 8h;A 0.9 mmol
B 1.0 mmol
C 0.1 mmol
Dilithium-bis(trimethylsilyl)tetrazenid
79345-33-8, 79345-34-9

Dilithium-bis(trimethylsilyl)tetrazenid

A

N,N'-bis(trimethylsilyl)hydrazine
692-56-8

N,N'-bis(trimethylsilyl)hydrazine

B

Dilithium N,N'-bis(trimethylsilyl)hydrazide tetramer
15114-92-8, 33509-48-7, 53380-51-1

Dilithium N,N'-bis(trimethylsilyl)hydrazide tetramer

C

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In benzene at 120℃; for 40h;A 0.1 mmol
B 1.5 mmol
C 0.2 mmol
Dilithium-bis(trimethylsilyl)tetrazenid
79345-33-8, 79345-34-9

Dilithium-bis(trimethylsilyl)tetrazenid

A

Dilithium N,N'-bis(trimethylsilyl)hydrazide tetramer
15114-92-8, 33509-48-7, 53380-51-1

Dilithium N,N'-bis(trimethylsilyl)hydrazide tetramer

B

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In diethyl ether at 120℃; for 15h;A 0.2 mmol
B 1.8 mmol
Lithium-tris(trimethylsilyl)tetrazenid
79345-35-0

Lithium-tris(trimethylsilyl)tetrazenid

A

tris(trimethylsilyl)amine
1586-73-8

tris(trimethylsilyl)amine

B

trimethylsilylazide
4648-54-8

trimethylsilylazide

C

N-lithio-N,N',N'-[tris(trimethylsilyl)]hydrazide
22846-03-3

N-lithio-N,N',N'-[tris(trimethylsilyl)]hydrazide

D

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In benzene at 25℃; for 6h;A 1.5 mmol
B 0.3 mmol
C 0.2 mmol
D 0.3 mmol
1-bromo-butane
109-65-9

1-bromo-butane

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

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

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
With lithium 1) 1 h mixing and 1 h reflux; 2) 30 min reflux; Yield given. Multistep reaction;
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

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

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

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In hexane
With tetramethylsilane In tetrahydrofuran; hexane at -73℃; for 0.0333333h;100 % Spectr.
In tetrahydrofuran; hexane at -78℃; for 1h;
In tetrahydrofuran at -78 - 20℃; for 1h; Product distribution / selectivity;
9H-fluoren-9-yllithium
881-04-9

9H-fluoren-9-yllithium

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

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

A

9H-fluorene
86-73-7

9H-fluorene

B

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 27℃; Equilibrium constant;
<(pyridin-2-yl)phenylmethyl>lithium
56501-99-6

<(pyridin-2-yl)phenylmethyl>lithium

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

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

A

2-Benzylpyridine
101-82-6

2-Benzylpyridine

B

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 27℃; Equilibrium constant;
<(pyridin-4-yl)phenylmethyl>lithium
81771-00-8

<(pyridin-4-yl)phenylmethyl>lithium

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

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

A

4-benzyl pyridine
2116-65-6

4-benzyl pyridine

B

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 27℃; Equilibrium constant;
Lithium; (1aR,2R,7aR)-2,7a-dimethyl-7-oxo-1a,2,7,7a-tetrahydro-1-oxa-cyclopropa[b]naphthalen-2-olate

Lithium; (1aR,2R,7aR)-2,7a-dimethyl-7-oxo-1a,2,7,7a-tetrahydro-1-oxa-cyclopropa[b]naphthalen-2-olate

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

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

(1aR,2R,7aR)-2-Hydroxy-2,7a-dimethyl-1a,7a-dihydro-2H-1-oxa-cyclopropa[b]naphthalen-7-one
125541-07-3

(1aR,2R,7aR)-2-Hydroxy-2,7a-dimethyl-1a,7a-dihydro-2H-1-oxa-cyclopropa[b]naphthalen-7-one

B

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; Thermodynamic data; ΔH;
Lithium; (1aR,7R,7aR)-1a,7,7a-trimethyl-2-oxo-1a,2,7,7a-tetrahydro-1-oxa-cyclopropa[b]naphthalen-7-olate

Lithium; (1aR,7R,7aR)-1a,7,7a-trimethyl-2-oxo-1a,2,7,7a-tetrahydro-1-oxa-cyclopropa[b]naphthalen-7-olate

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

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

(1aR,7R,7aR)-7-Hydroxy-1a,7,7a-trimethyl-7,7a-dihydro-1aH-1-oxa-cyclopropa[b]naphthalen-2-one
68437-75-2, 125637-05-0

(1aR,7R,7aR)-7-Hydroxy-1a,7,7a-trimethyl-7,7a-dihydro-1aH-1-oxa-cyclopropa[b]naphthalen-2-one

B

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; Thermodynamic data; ΔH;
C10H8LiN
97254-19-8

C10H8LiN

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

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

A

C6H4NCH2CHCCH2
491-35-0

C6H4NCH2CHCCH2

B

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 27℃; Equilibrium constant;
Dilithium N,N'-bis(trimethylsilyl)hydrazide tetramer
15114-92-8, 33509-48-7, 53380-51-1

Dilithium N,N'-bis(trimethylsilyl)hydrazide tetramer

A

N,N'-bis(trimethylsilyl)hydrazine
692-56-8

N,N'-bis(trimethylsilyl)hydrazine

B

tetrakis(trimethylsilyl)hydrazine
20156-62-1

tetrakis(trimethylsilyl)hydrazine

C

tris(trimethylsilyl)hydrazine
13272-02-1

tris(trimethylsilyl)hydrazine

D

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

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

E

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
With tin(ll) chloride In diethyl ether for 48h; Product distribution; Ambient temperature; var.: reagent;
C17H17O3S(1-)*C6H18NSi2(1-)*2Li(1+)

C17H17O3S(1-)*C6H18NSi2(1-)*2Li(1+)

A

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

B

p-phenylsulfonylisobutyrophenone lithium enolate

p-phenylsulfonylisobutyrophenone lithium enolate

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; Equilibrium constant;
C23H17O(1-)*C6H18NSi2(1-)*2Li(1+)

C23H17O(1-)*C6H18NSi2(1-)*2Li(1+)

A

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

B

6-phenyl-2-benzyl-α-tetralone lithium enolate

6-phenyl-2-benzyl-α-tetralone lithium enolate

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; Equilibrium constant;
2-(1,3-isoindolinedion-2-yl)-5-(2-methylpropionyl)indane
172680-90-9

2-(1,3-isoindolinedion-2-yl)-5-(2-methylpropionyl)indane

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

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

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

A

2-(1,3-isoindolinedion-2-yl)-5-(2,2-dimethyl-3-methoxycarbonyl-propionyl)indane
172680-91-0

2-(1,3-isoindolinedion-2-yl)-5-(2,2-dimethyl-3-methoxycarbonyl-propionyl)indane

B

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
With n-butyllithium; ammonium chloride In tetrahydrofuran; hexane
n-butyllithium (1.60M)-hexane

n-butyllithium (1.60M)-hexane

3-(trimethylsilyl)prop-2-yn-1-al
2975-46-4

3-(trimethylsilyl)prop-2-yn-1-al

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

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

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In tetrahydrofuran
(η5-C5H4Li)Re(NO)(PPh3)(CH3)

(η5-C5H4Li)Re(NO)(PPh3)(CH3)

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

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

A

(η5-C5H5)(Me)(NO)(PPh3)rhenium(II)

(η5-C5H5)(Me)(NO)(PPh3)rhenium(II)

B

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In tetrahydrofuran conducted under dry N2 atmosphere; equilibrium at -24°C;; monitored by (31)P-NMR-spectroscopy;;A >99
B n/a
Li(1+){(η5-C5H5)Re(NO)(PPh3)}(1-)

Li(1+){(η5-C5H5)Re(NO)(PPh3)}(1-)

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

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

A

(η5-cyclopentadienyl)rhenium(NO)(PPh3)(hydride)

(η5-cyclopentadienyl)rhenium(NO)(PPh3)(hydride)

B

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In not given conducted under dry N2 atmosphere; complete transformation at -24°C after 2 d;; monitored by (31)P-NMR-spectroscopy;;A >99
B n/a
germanium(II) chloride-dioxan

germanium(II) chloride-dioxan

chlorobis(trimethylsilyl)methane
5926-35-2

chlorobis(trimethylsilyl)methane

lithium
7439-93-2

lithium

lithium bis(trimethylsilyl)amide diethyl etherate
18400-61-8

lithium bis(trimethylsilyl)amide diethyl etherate

A

bis[bis(trimethylsilyl)methyl]germanium(II) dimer
62487-23-4

bis[bis(trimethylsilyl)methyl]germanium(II) dimer

B

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In diethyl ether byproducts: LiCl; dry Ar-atmosphere; dropwise addn. of Li-reagent (prepd. from (Me3Si)2CH2Cl and Li-powder by refluxing for 24 h and filtration off of LiCl) to soln. of equimolar amt. of Ge-amide (prepd. from GeCl2 and Li-amide) at 0°C; removal of volatiles (0°C, 0.01 Torr), extn. into hexane, repeated crystn.; product mixt. not sepd.;
cesium bis(trimethylsilyl)amide

cesium bis(trimethylsilyl)amide

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran
2: tetrahydrofuran
View Scheme
2,3-benzofluorene lithium salt

2,3-benzofluorene lithium salt

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

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

A

2,3-benzofluorene
243-17-4

2,3-benzofluorene

B

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In tetrahydrofuran Equilibrium constant; Concentration;
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

hexamethyldisilazan
72525-60-1

hexamethyldisilazan

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Conditions
ConditionsYield
In 1,2-dimethoxyethane; hexane
trans-but-2-enyl chloride
4894-61-5

trans-but-2-enyl chloride

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

2-((E)-But-2-enyl)-1,1,1,3,3,3-hexamethyl-disilazane
89333-64-2

2-((E)-But-2-enyl)-1,1,1,3,3,3-hexamethyl-disilazane

Conditions
ConditionsYield
With silver(I) iodide In tetrahydrofuran for 1.5h; Heating;100%
2-Chlor-4,4,5,5-tetrakis(trifluormethyl)-1,3,2λ3-dioxaphospholan
70311-64-7

2-Chlor-4,4,5,5-tetrakis(trifluormethyl)-1,3,2λ3-dioxaphospholan

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

2-Bis(trimethylsilyl)amino-4,4,5,5-tetrakis(trifluormethyl)-1,3,2λ3-dioxaphospholan
79824-04-7

2-Bis(trimethylsilyl)amino-4,4,5,5-tetrakis(trifluormethyl)-1,3,2λ3-dioxaphospholan

Conditions
ConditionsYield
at 25℃; for 24h;100%
m-iodobenzaldehyde
696-41-3

m-iodobenzaldehyde

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

[1-(3-Iodo-phenyl)-meth-(E)-ylidene]-trimethylsilanyl-amine
253327-53-6

[1-(3-Iodo-phenyl)-meth-(E)-ylidene]-trimethylsilanyl-amine

Conditions
ConditionsYield
In tetrahydrofuran Substitution;100%
lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

(3aS,4S,6S,7aR)-2-[(1S)-1-chloro-3-methylbutyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole
85167-14-2

(3aS,4S,6S,7aR)-2-[(1S)-1-chloro-3-methylbutyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole

1,1,1-trimethyl-N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}-N-(trimethylsilyl)silanamine
514820-48-5

1,1,1-trimethyl-N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}-N-(trimethylsilyl)silanamine

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 20℃;100%
In tetrahydrofuran at -78 - 20℃;100%
In tetrahydrofuran at -40℃; for 1h; Inert atmosphere;97.7%
2,5-di-tert-butyl-7-methyl-phenanthridinium; trifluoro-methanesulfonate

2,5-di-tert-butyl-7-methyl-phenanthridinium; trifluoro-methanesulfonate

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

2,5-di-tert-butyl-6-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-7-methyl-5,6-dihydro-phenanthridine

2,5-di-tert-butyl-6-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-7-methyl-5,6-dihydro-phenanthridine

Conditions
ConditionsYield
In tetrahydrofuran-d8 at -78℃;100%
(+)-pinanediol 1-chloro-3-methylbutane-1-boronate

(+)-pinanediol 1-chloro-3-methylbutane-1-boronate

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

N,N-bis(trimethylsilyl)-(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutylamine

N,N-bis(trimethylsilyl)-(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutylamine

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 20℃;100%
In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
C33H23BClF15GeN2O

C33H23BClF15GeN2O

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

C39H41BF15GeN3OSi2

C39H41BF15GeN3OSi2

Conditions
ConditionsYield
In toluene at 0 - 20℃; for 12h;100%
(S)-1-chloro-2,2-d2-3-methylbutylboronic acid-(+)-pinanediol ester

(S)-1-chloro-2,2-d2-3-methylbutylboronic acid-(+)-pinanediol ester

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

(R)-1-(hexamethyldisilanyl)amino-2,2-d2-3-methylbutylboronic acid pinanediol ester

(R)-1-(hexamethyldisilanyl)amino-2,2-d2-3-methylbutylboronic acid pinanediol ester

Conditions
ConditionsYield
In tetrahydrofuran at -40 - 20℃; for 2h; Inert atmosphere;100%
(S)-1-chloro-1-d1-2,2-d2-3-methylbutylboronic acid-(+)-pinanediol ester

(S)-1-chloro-1-d1-2,2-d2-3-methylbutylboronic acid-(+)-pinanediol ester

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

(R)-1-(hexamethyldisilanyl)amino-1-d1-2,2-d2-3-methylbutylboronic acid pinanediol ester

(R)-1-(hexamethyldisilanyl)amino-1-d1-2,2-d2-3-methylbutylboronic acid pinanediol ester

Conditions
ConditionsYield
In tetrahydrofuran at -40 - 20℃; for 2h; Inert atmosphere;100%
H2[bis(diisopropylphenylbenzimidazol-2-ylidene)phenyl]Fe(II)Cl3

H2[bis(diisopropylphenylbenzimidazol-2-ylidene)phenyl]Fe(II)Cl3

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

trimethylphosphane
594-09-2

trimethylphosphane

(bis(diisopropylphenylbenzimidazol-2-ylidene)phenyl)Fe(II)H(PMe3)(N2)

(bis(diisopropylphenylbenzimidazol-2-ylidene)phenyl)Fe(II)H(PMe3)(N2)

Conditions
ConditionsYield
With potassium graphite In tetrahydrofuran; toluene at 20℃;100%
2-bromo-3-methylphenol
22061-78-5

2-bromo-3-methylphenol

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

3-methyl-2-(trimethylsilyl)phenol

3-methyl-2-(trimethylsilyl)phenol

Conditions
ConditionsYield
Stage #1: 2-bromo-3-methylphenol; lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
100%
bis(1,5-cyclooctadiene)diiridium(I) dichloride
12112-67-3

bis(1,5-cyclooctadiene)diiridium(I) dichloride

1,1'-(3,6-di-tert-butyl-9H-carbazol-1,8-diyl)bis(3-but-3-enyl-1H-imidazolium) dibromide

1,1'-(3,6-di-tert-butyl-9H-carbazol-1,8-diyl)bis(3-but-3-enyl-1H-imidazolium) dibromide

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

C34H40IrN5*2LiBr*LiCl

C34H40IrN5*2LiBr*LiCl

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;100%
2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

lithium cyanide
788104-34-7, 25733-05-5

lithium cyanide

Conditions
ConditionsYield
In tetrahydrofuran addn. of lithium compd. to a soln. of cyanohydrin in THF at 0°C, stirring for 30 min; evapn.;99%
bis(bis(trimethylsilyl)amido)zinc(II)

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

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

lithium tris{bis(trimethylsilyl)amido}zincate*4 THF

lithium tris{bis(trimethylsilyl)amido}zincate*4 THF

Conditions
ConditionsYield
With tetrahydrofuran In tetrahydrofuran stirring under Ar, room temp., 2h; evapn.; elem. anal.;99%
indium chloride

indium chloride

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

indium(I) bis(trimethylsilyl)amide

indium(I) bis(trimethylsilyl)amide

Conditions
ConditionsYield
In tetrahydrofuran byproducts: LiCl; under dry Ar or N2, Li-compd. in THF was added to THF soln. of InCl at -78 °C, warming to 25 °C; LiCl was filtered off, volatiles were removed in vac.;99%
[(η5-pentamethylcyclopentadienyl)Ta(N-tert-butyl)(CH3)Cl]
291538-02-8

[(η5-pentamethylcyclopentadienyl)Ta(N-tert-butyl)(CH3)Cl]

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

[(η5-pentamethylcyclopentadienyl)Ta(N-tert-butyl)(CH3)(N(Si(CH3)3)2)]

[(η5-pentamethylcyclopentadienyl)Ta(N-tert-butyl)(CH3)(N(Si(CH3)3)2)]

Conditions
ConditionsYield
In benzene-d6 byproducts: LiCl; C6D6 added in NMR tube to solid mixture under Ar, at 90°C for 24 h; not isolated, identified by NMR;99%
Salen((t)Bu)AlCl
182315-48-6

Salen((t)Bu)AlCl

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

(((CH3)3Si)2N)Al((CH2NCHC6H2(C(CH3)3)2O)2)
182315-59-9

(((CH3)3Si)2N)Al((CH2NCHC6H2(C(CH3)3)2O)2)

Conditions
ConditionsYield
In toluene stirring (35°C, 48 h); filtering, evapn. (reduced pressure); elem. anal.;99%
TaCl2(dimethylamide)3
224638-03-3

TaCl2(dimethylamide)3

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

((CH3)2N)3TaCl(N(Si(CH3)3)2)
652161-03-0

((CH3)2N)3TaCl(N(Si(CH3)3)2)

Conditions
ConditionsYield
In pentane byproducts: LiCl; under N2 atm. (Me2N)3TaCl2 was mixed with LiN(SiMe3)2 (1 : 1) and pentane was added at -50°C, react. mixt, was allowed to warm to room temp. and stirred overnight; soln. was filtered, volatiles were removed in vacuo; elem. anal.;99%
4,4'-diisopropyl-1,1'-dimethoxy-1,6,1',6'-tetrahydro-[2,2']biborininyl

4,4'-diisopropyl-1,1'-dimethoxy-1,6,1',6'-tetrahydro-[2,2']biborininyl

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

2Li(1+)*((CH3)2CHC5H3BOCH3)2(2-)=Li2((CH3)2CHC5H3BOCH3)2

2Li(1+)*((CH3)2CHC5H3BOCH3)2(2-)=Li2((CH3)2CHC5H3BOCH3)2

Conditions
ConditionsYield
In tetrahydrofuran addn. of LiN(TMS)2 in THF to a soln. diborabiphenyl derivative in THF atroom temp. under stiring, stirring for 1 h at room temp.; removal of volatiles under vac.,;99%
3-(1,3-benzoxazol-2-yl)naphthalen-2-ol
14967-45-4

3-(1,3-benzoxazol-2-yl)naphthalen-2-ol

tris(bistrimethylsilylamine)scandium(III)

tris(bistrimethylsilylamine)scandium(III)

lithium hexamethyldisilazane
4039-32-1

lithium hexamethyldisilazane

Sc(3+)*Li(1+)*4C17H10NO2(1-)

Sc(3+)*Li(1+)*4C17H10NO2(1-)

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 70℃; for 4h;99%

Lithium bis(trimethylsilyl)amide Chemical Properties

Molecular Structure:

Molecular Formula: C6H18LiNSi2
Molecular Weight: 167.3258
IUPAC Name: [Dimethyl-(trimethylsilylamino)silyl]methane
Synonyms of Lithium bis(trimethylsilyl)amide (CAS NO.4039-32-1): Bis(trimethylsilyl)amido lithium ; Bis(trimethylsilyl)amidolithium ; Disilazane, 1,1,1,3,3,3-hexamethyl-, lithium salt ; EINECS 223-725-6 ; Hexamethyldisilazane lithium salt ; Lithium hexamethyldisilazane ; Lithium tris(trimethylsilyl)amine ; Lithium, (bis(trimethylsilyl)amino)- ; Lithiumbis(trimethylsilyl)amine ; N-Lithiohexamethyldisilazane ; NSC 252161 ; Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, lithium salt ; Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, lithium salt (1:1)
CAS NO: 4039-32-1
Classification Code: Classes of Metal Compounds ; Li (Lithium) Compounds ; Si (Classes of Silicon Compounds);Silazanes;Silicon Compounds (for Synthesis) ; Si-N Compounds ; Synthetic Organic Chemistry ; Typical Metal Compounds
Melting point: 73°C 
H bond acceptors: 1 
Freely Rotating Bonds: 3

Lithium bis(trimethylsilyl)amide Uses

 Lithium bis(trimethylsilyl)amide (CAS NO.4039-32-1) can be used for the aldol condensation, and also is commonly used organic base.

Lithium bis(trimethylsilyl)amide Safety Profile

Hazard Codes of Lithium bis(trimethylsilyl)amide (CAS NO.4039-32-1): FlammableF,CorrosiveC,DangerousN
Risk Statements: 11-34-48/20-63-65-67-51/53-35-62-14 
R11: Highly flammable. 
R34: Causes burns. 
R48: Danger of serious damage to health by prolonged exposure. 
R20: Harmful by inhalation. 
R63: Possible risk of harm to the unborn child. 
R65: Harmful: may cause lung damage if swallowed. 
R67: Vapours may cause drowsiness and dizziness. 
R51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R35: Causes severe burns. 
R62: Risk of impaired fertility. 
R14: Reacts violently with water.
Safety Statements: 9-16-26-29-33-36/37/39-45-61-62-57-43 
S9: Keep container in a well-ventilated place. 
S16: Keep away from sources of ignition. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S29: Do not empty into drains. 
S33: Take precautionary measures against static discharges. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S61: Avoid release to the environment. Refer to special instructions / safety data sheets. 
S62: If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. 
S57: Use appropriate container to avoid environmental contamination. 
S43: In case of fire use ... (there follows the type of fire-fighting equipment to be used.)
RIDADR: UN 2925 4.1/PG 2
WGK Germany: 3
F: 10-23
TSCA: Yes
HazardClass: 4.3
PackingGroup: II
Unstable in air. Ignites when compressed. Upon decomposition it emits toxic fumes of LI2O and NOx. See also LITHIUM COMPOUNDS, SILANE, and AMIDES.

Lithium bis(trimethylsilyl)amide Specification

Stability and Reactivity of Lithium bis(trimethylsilyl)amide (CAS NO.4039-32-1).
Chemical Stability: Moisture sensitive. 
Conditions to Avoid: Incompatible materials, ignition sources, exposure to moist air or water. 
Incompatibilities with Other Materials Oxidizing materials, water, acids. 
Hazardous Decomposition Products Nitrogen oxides, carbon monoxide, carbon dioxide, silicon dioxide, lithium oxide. 
Hazardous Polymerization Has not been reported. 
First Aid Measures.
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin: Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. 
Ingestion: Do not induce vomiting. Get medical aid immediately. 
Inhalation: Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. 
Notes to Physician: Treat symptomatically and supportively. 
Handling and Storage of:
Handling: Use spark-proof tools and explosion proof equipment. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Handle under an inert atmosphere. Use only in a chemical fume hood. 
Storage: Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container. Flammables-area. Corrosives area. Store under nitrogen. 

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