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Cas Database |
| Name |
(Trimethylsilyl)methyllithium |
EINECS | N/A |
| CAS No. | 1822-00-0 | Density | 0.65 g/mL at 25 °C |
| PSA | 0.00000 | LogP | 1.83140 |
| Solubility | N/A | Melting Point |
112-117 °C (decomp) |
| Formula | C4H11LiSi | Boiling Point | 35-36 °C |
| Molecular Weight | 94.1578 | Flash Point | -49 °C |
| Transport Information | UN 3399 | Appearance | N/A |
| Safety | 16-26-33-36/37/39-43-45-61-62 | Risk Codes | 11-14-34-51/53-65-66-67 |
| Molecular Structure |
|
Hazard Symbols |
 F, C, N
|
| Synonyms |
Silane,tetramethyl-, lithium complex;(Lithiomethyl)trimethylsilane;[(Trimethylsilyl)methyl]lithium; |
Article Data | 13 |
(Trimethylsilyl)methyllithium Synthetic route
| Conditions | Yield |
|---|---|
| In pentane | 95% |
| In pentane | 95% |
| In pentane at 40℃; for 16h; Argon gasification; | 80% |
| Conditions | Yield |
|---|---|
| With tert.-butyl lithium In diethyl ether -78 deg C, 0.5-1h, warmed to 23 deg C in 0.5-1h; | 90 % Spectr. |
- 77425-85-5
(trimethylsilyl)(tributylstannyl)methane
- 1822-00-0
trimethylsilylmethyllithium
| Conditions | Yield |
|---|---|
| With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; |
| Conditions | Yield |
|---|---|
| With lithium In pentane for 10h; Heating; | 700 mg |
| With lithium In n-heptane at 55 - 60℃; for 5h; | |
| With lithium In hexane for 0.5 - 1.5h; Heating / reflux; |
| Conditions | Yield |
|---|---|
| In not given under N2 or Ar, at room temp. in either PhMe-d8 or THF-d8; not isolated; monitored by NMR; |
- 1822-00-0
trimethylsilylmethyllithium
- 218614-13-2
(-)-methyl (3S)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpentanoate
- 218614-14-3
(4S)-4,6-bis{[tert-butyl(dimethyl)silyl]oxy}-3,3-dimethylhexan-2-one
| Conditions | Yield |
|---|---|
| In pentane at 0℃; for 3.5h; | 100% |
| Stage #1: trimethylsilylmethyllithium; (-)-methyl (3S)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpentanoate In pentane at 0℃; for 4h; Stage #2: With methanol at 20℃; for 1h; Further stages.; | 97% |
| With methanol 1.) pentane, 0 deg C, 4 h; 2.) r.t., 1 h; Yield given. Multistep reaction; | |
| With methanol Substitution; |
- 1822-00-0
trimethylsilylmethyllithium
- 218614-13-2
(-)-methyl (3S)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpentanoate
| Conditions | Yield |
|---|---|
| Stage #1: trimethylsilylmethyllithium; (-)-methyl (3S)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpentanoate In pentane at 0℃; for 3.25h; Stage #2: With methanol In pentane at 0 - 20℃; for 5h; | 100% |
- 1822-00-0
trimethylsilylmethyllithium
| Conditions | Yield |
|---|---|
| Stage #1: 4,6,6-trimethyl-5,6,7,7a-tetrahydro-1,3-benzodioxol-5-one; trimethylsilylmethyllithium In tetrahydrofuran; pentane at -20 - 20℃; for 0.666667h; Argon gasification; Stage #2: With water In tetrahydrofuran; pentane | 100% |
| Conditions | Yield |
|---|---|
| In tetrahydrofuran; water; pentane | 100% |
(Trimethylsilyl)methyllithium Specification
The IUPAC name of (Trimethylsilyl)methyllithium is lithium methanidyl(trimethyl)silane. With the CAS registry number 1822-00-0, it is also named as Lithium,[(trimethylsilyl)methyl]-. The product's categories are Alkyl; Organolithium; Organometallic Reagents. Besides, it should be sealed in a cool and dark place at 2-8 °C. In addition, its molecular formula is C4H11LiSi and molecular weight is 94.16.
The other characteristics of this product can be summarized as: (1)H-Bond Donor: 0; (2)H-Bond Acceptor: 1; (3)Rotatable Bond Count: 0; (4)Exact Mass: 94.079006; (5)MonoIsotopic Mass: 94.079006; (6)Topological Polar Surface Area: 0; (7)Heavy Atom Count: 6; (8)Complexity: 29; (9)Flash Point: -49 °C; (10)Boiling Point: 35-36 °C; (11)Density: 0.65 g/mL at 25 °C; (12)Concentration: 1.4 M in cyclohexane.
Uses of (Trimethylsilyl)methyllithium: it can react with cyclohex-2-enone to get 1-trimethylsilylmethyl-2-cyclohexen-1-ol.
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This reaction needs diethyl ether at temperature of 25 °C for 15 min. The yield is 93 %.
When you are using this chemical, please be cautious about it as the following: it is highly flammable that may cause burns. Please keep away from sources of ignition. It also reacts violently with water. Moreover, it is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. You should avoid release to the environment, and refer to special instructions / safety data sheets. It is harmful that may cause lung damage if swallowed. If swallowed, please do not induce vomitting; seek medical advice immediately and show this container or label. And it may cause skin dryness or cracking if repeated exposure. Its vapours may cause drowsiness and dizziness. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Additionally, please take precautionary measures against static discharges. And you should wear suitable protective clothing, gloves and eye/face protection. Furthermore, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: [Li+].C[Si](C)(C)[CH2-]
(2)InChI: InChI=1S/C4H11Si.Li/c1-5(2,3)4;/h1H2,2-4H3;/q-1;+1
(3)InChIKey: KVWLUDFGXDFFON-UHFFFAOYSA-N
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