Lithium bis(trimethylsilyl)amide
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Lithium bis(trimethylsilyl)amide
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CAS No:
4039-32-1
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Formula:
C6H19NSi2.Li
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Chemical Name:
Lithium bis(trimethylsilyl)amide
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Synonyms:
Silanamine,1,1,1-trimethyl-N-(trimethylsilyl)-,lithium salt (1:1);Silanamine,1,1,1-trimethyl-N-(trimethylsilyl)-,lithium salt;Lithium,[bis(trimethylsilyl)amino]-;Disilazane,1,1,1,3,3,3-hexamethyl-,lithium salt;Disilazane,1,1,1,3,3,3-hexamethyl-,Li deriv.;Lithium hexamethyldisilazane;Bis(trimethylsilyl)amidolithium;Hexamethyldisilazane lithium salt;Lithium bis(trimethylsilyl)amine;Lithium hexamethyldisilazide;1,1,1,3,3,3-Hexamethyldisilazane lithium salt;Lithiobis(trimethylsilyl)amide;Lithium hexamethyldisilazanide;Lithiohexamethyldisilazane;Lithium bis(trimethylsilyl)amide;Lithium hexamethyldisilazanate;[1,1,1-Trimethyl-N-(trimethylsilyl)silanaminato]lithium;(Hexamethyldisilazane)lithium;1,1,1-Trimethyl-N-(trimethylsilyl)silanamine lithium salt;N-Lithiohexamethyldisilazane;N,N-Bis(trimethylsilyl)amine lithium salt;LiHMDS;Lithium bis(trimethylsilyl)amide(1-);LHMDS;66568-21-6;68092-53-5;97462-05-0;166307-01-3;170947-20-3;330660-50-9;552321-61-6;618461-92-0;1085692-82-5;1116027-23-6;1314137-48-8;1639136-05-2;2235416-87-0
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CAS No:
Description
light yellow to yellow crystalline powder
Lithium bis(trimethylsilyl)amide is a lithiated organosilicon compound with the formula LiN(SiMe3)2. It is commonly abbreviated as LiHMDS (Lithium HexaMethylDiSilazide - a reference to its starting material HMDS) and is primarily used as a strong non-nucleophilic base and as a ligand. Like many lithium reagents it has a tendency to aggregate and will form a cyclic trimer in the absence of coordinating species.
Liquid
Lithium bis(trimethylsilyl)amide Basic Attributes
167.33
167.114
223-725-6
RC4N1I108M
DTXSID2044426
2931900090
Characteristics
1
2.42250
White Powder
0.891 g/cm3
70-71 °C
110-115 °C @ Press: 1 Torr
48 °F
n20/D 1.425(lit.)
hydrolysis
below 5° C
Safety Information
II
4.3
UN 2925 4.1/PG 2
3
11-34-48/20-63-65-67-51/53-35-20-62-14-40-37-19
9-16-26-29-33-36/37/39-45-61-62-57-43
F,C,N
Stable at normal temperatures in tightly closed containers under an inert atmosphere.
P210, P240, P241, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P405, P501
H228
UN 2925 4.1/PG 2
P210; P260; P280; P305 + P351 + P338; P370 + P378; P403 + P235
|Danger|H228 (47.19%): Flammable solid [Danger Flammable solids]|P210, P240, P241, P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P370+P378, P405, and P501|Aggregated GHS information provided by 178 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Lithium bis(trimethylsilyl)amide Use and Manufacturing
Non-nucleophilic strong base, can be used for the formation of enol reaction, the enol ester stereospecific Claisen rearrangement reaction, the conversion of aldehyde to silimide reaction, the formation of glycidyl ester reaction, β lactam Reaction, selective cleavage of aryl alkyl ethers.
Intermediates
All other basic organic chemical manufacturing|Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, lithium salt (1:1): ACTIVE
Computed Properties
Molecular Weight:167.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:167.11378108
Monoisotopic Mass:167.11378108
Topological Polar Surface Area:1
Heavy Atom Count:10
Complexity:80.9
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
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Lithium bis(trimethylsilyl)amide
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