Conditions | Yield |
---|---|
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
lithium hexamethyldisilazane
N,N,N'-tris(trimethylsilyl)phosphenimidous amide
2,2,6,6-tetramethylpiperidinyl-lithium
A
N-trimethylsilylimidophosphenous acid 2,2,6,6-tetramethylpiperidine
B
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran at 40℃; for 3h; | A 4.6 g B n/a |
tetrakis(trimethylsilyl)tetrazene
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
With lithium In diethyl ether at 36℃; for 72h; | 20 % Spectr. |
Lithium-bis(trimethylsilyl)tetrazenid
A
N,N'-bis(trimethylsilyl)hydrazine
B
Dilithium-bis(trimethylsilyl)tetrazenid
C
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In diethyl ether at 70℃; for 8h; | A 0.9 mmol B 1.0 mmol C 0.1 mmol |
Dilithium-bis(trimethylsilyl)tetrazenid
A
N,N'-bis(trimethylsilyl)hydrazine
B
Dilithium N,N'-bis(trimethylsilyl)hydrazide tetramer
C
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In benzene at 120℃; for 40h; | A 0.1 mmol B 1.5 mmol C 0.2 mmol |
Dilithium-bis(trimethylsilyl)tetrazenid
A
Dilithium N,N'-bis(trimethylsilyl)hydrazide tetramer
B
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In diethyl ether at 120℃; for 15h; | A 0.2 mmol B 1.8 mmol |
Lithium-tris(trimethylsilyl)tetrazenid
A
tris(trimethylsilyl)amine
B
trimethylsilylazide
C
N-lithio-N,N',N'-[tris(trimethylsilyl)]hydrazide
D
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
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
1,1,1,3,3,3-hexamethyl-disilazane
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
With lithium 1) 1 h mixing and 1 h reflux; 2) 30 min reflux; Yield given. Multistep reaction; |
n-butyllithium
1,1,1,3,3,3-hexamethyl-disilazane
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
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
1,1,1,3,3,3-hexamethyl-disilazane
A
9H-fluorene
B
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 27℃; Equilibrium constant; |
<(pyridin-2-yl)phenylmethyl>lithium
1,1,1,3,3,3-hexamethyl-disilazane
A
2-Benzylpyridine
B
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 27℃; Equilibrium constant; |
<(pyridin-4-yl)phenylmethyl>lithium
1,1,1,3,3,3-hexamethyl-disilazane
A
4-benzyl pyridine
B
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 27℃; Equilibrium constant; |
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
B
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran at 25℃; Thermodynamic data; ΔH; |
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
B
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran at 25℃; Thermodynamic data; ΔH; |
C10H8LiN
1,1,1,3,3,3-hexamethyl-disilazane
A
C6H4NCH2CHCCH2
B
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 27℃; Equilibrium constant; |
Dilithium N,N'-bis(trimethylsilyl)hydrazide tetramer
A
N,N'-bis(trimethylsilyl)hydrazine
B
tetrakis(trimethylsilyl)hydrazine
C
tris(trimethylsilyl)hydrazine
D
1,1,1,3,3,3-hexamethyl-disilazane
E
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
With tin(ll) chloride In diethyl ether for 48h; Product distribution; Ambient temperature; var.: reagent; |
A
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran at 25℃; Equilibrium constant; |
A
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran at 25℃; Equilibrium constant; |
2-(1,3-isoindolinedion-2-yl)-5-(2-methylpropionyl)indane
bromoacetic acid methyl ester
1,1,1,3,3,3-hexamethyl-disilazane
A
2-(1,3-isoindolinedion-2-yl)-5-(2,2-dimethyl-3-methoxycarbonyl-propionyl)indane
B
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
With n-butyllithium; ammonium chloride In tetrahydrofuran; hexane |
3-(trimethylsilyl)prop-2-yn-1-al
1,1,1,3,3,3-hexamethyl-disilazane
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran |
Conditions | Yield |
---|---|
In tetrahydrofuran conducted under dry N2 atmosphere; equilibrium at -24°C;; monitored by (31)P-NMR-spectroscopy;; | A >99 B n/a |
Conditions | Yield |
---|---|
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 |
chlorobis(trimethylsilyl)methane
lithium
lithium bis(trimethylsilyl)amide diethyl etherate
A
bis[bis(trimethylsilyl)methyl]germanium(II) dimer
B
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
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.; |
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran 2: tetrahydrofuran View Scheme |
1,1,1,3,3,3-hexamethyl-disilazane
A
2,3-benzofluorene
B
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran Equilibrium constant; Concentration; |
n-butyllithium
hexamethyldisilazan
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane; hexane |
trans-but-2-enyl chloride
lithium hexamethyldisilazane
2-((E)-But-2-enyl)-1,1,1,3,3,3-hexamethyl-disilazane
Conditions | Yield |
---|---|
With silver(I) iodide In tetrahydrofuran for 1.5h; Heating; | 100% |
2-Chlor-4,4,5,5-tetrakis(trifluormethyl)-1,3,2λ3-dioxaphospholan
lithium hexamethyldisilazane
2-Bis(trimethylsilyl)amino-4,4,5,5-tetrakis(trifluormethyl)-1,3,2λ3-dioxaphospholan
Conditions | Yield |
---|---|
at 25℃; for 24h; | 100% |
m-iodobenzaldehyde
lithium hexamethyldisilazane
[1-(3-Iodo-phenyl)-meth-(E)-ylidene]-trimethylsilanyl-amine
Conditions | Yield |
---|---|
In tetrahydrofuran Substitution; | 100% |
lithium hexamethyldisilazane
(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
Conditions | Yield |
---|---|
In tetrahydrofuran at -78 - 20℃; | 100% |
In tetrahydrofuran at -78 - 20℃; | 100% |
In tetrahydrofuran at -40℃; for 1h; Inert atmosphere; | 97.7% |
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran-d8 at -78℃; | 100% |
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran at -78 - 20℃; | 100% |
In tetrahydrofuran at -78 - 20℃; Inert atmosphere; |
Conditions | Yield |
---|---|
In toluene at 0 - 20℃; for 12h; | 100% |
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran at -40 - 20℃; for 2h; Inert atmosphere; | 100% |
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran at -40 - 20℃; for 2h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With potassium graphite In tetrahydrofuran; toluene at 20℃; | 100% |
2-bromo-3-methylphenol
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
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
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique; | 100% |
2-hydroxy-2-methylpropanenitrile
lithium hexamethyldisilazane
lithium cyanide
Conditions | Yield |
---|---|
In tetrahydrofuran addn. of lithium compd. to a soln. of cyanohydrin in THF at 0°C, stirring for 30 min; evapn.; | 99% |
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
With tetrahydrofuran In tetrahydrofuran stirring under Ar, room temp., 2h; evapn.; elem. anal.; | 99% |
Conditions | Yield |
---|---|
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]
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
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
lithium hexamethyldisilazane
(((CH3)3Si)2N)Al((CH2NCHC6H2(C(CH3)3)2O)2)
Conditions | Yield |
---|---|
In toluene stirring (35°C, 48 h); filtering, evapn. (reduced pressure); elem. anal.; | 99% |
TaCl2(dimethylamide)3
lithium hexamethyldisilazane
((CH3)2N)3TaCl(N(Si(CH3)3)2)
Conditions | Yield |
---|---|
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% |
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
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
lithium hexamethyldisilazane
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane at 70℃; for 4h; | 99% |
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 (CAS NO.4039-32-1) can be used for the aldol condensation, and also is commonly used organic base.
Hazard Codes of Lithium bis(trimethylsilyl)amide (CAS NO.4039-32-1): F,C,N
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.
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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