(Trimethylsilyl)methyllithium supplier

Name
(TRIMETHYLSILYL)METHYLLITHIUM
EINECS
CAS No. 1822-00-0
Article Data13
CAS DataBase
Density 0.65 g/mL at 25 °C
Solubility
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
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;
PSA 0.00000
LogP 1.83140

Synthetic route

: 7439-93-2
lithium

: 2344-80-1
Chloromethyltrimethylsilane

: 1822-00-0
trimethylsilylmethyllithium

Conditions

Conditions	Yield
In pentane	95%
In pentane	95%
In pentane at 40℃; for 16h; Argon gasification;	80%

: 4206-67-1
iodo(trimethylsilyl)methane

: 1822-00-0
trimethylsilylmethyllithium

Conditions

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

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h;

: 2344-80-1
Chloromethyltrimethylsilane

: 1822-00-0
trimethylsilylmethyllithium

Conditions

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;

: 2344-80-1
Chloromethyltrimethylsilane

: 109-66-0
pentane

lithium: lithium

: 1822-00-0
trimethylsilylmethyllithium

...Expand

: C8H12*Rh(1+)*2(CH3)3SiCH2(1-)*Li(1+)=(C8H12)Rh(CH2Si(CH3)3)2Li

: 7412-67-1
neopentyl lithium

A: C8H12*Rh(1+)*2(CH3)3CCH2(1-)*Li(1+)=(C8H12)Rh(CH2C(CH3)3)2Li

B: 1822-00-0
trimethylsilylmethyllithium

Conditions

Conditions	Yield
In not given under N2 or Ar, at room temp. in either PhMe-d8 or THF-d8; not isolated; monitored by NMR;

...Expand

: 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

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

: 4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-1-trimethylsilanyl-hexan-2-one

Conditions

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%

: 4,6,6-trimethyl-5,6,7,7a-tetrahydro-1,3-benzodioxol-5-one

: 1822-00-0
trimethylsilylmethyllithium

: 4,6,6-trimethyl-5,6,7,7a-tetrahydro-5-trimethylsilylmethyl-1,3-benzodioxol-5-ol

Conditions

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%

: 4,6,6-trimethyl-5,6,7,7a-tetrahydro-1,3-benzodioxol-5-one

: 1822-00-0
trimethylsilylmethyllithium

: 2344-80-1
Chloromethyltrimethylsilane

: 7580-67-8
lithium hydride

: 4,6,6-trimethyl-5,6,7,7a-tetrahydro-5-trimethylsilylmethyl-1,3-benzodioxol-5-ol

Conditions

Conditions	Yield
In tetrahydrofuran; water; pentane	100%

...Expand

: 181037-28-5
Ti(N(C(CD3)2CH3)C6H3(CH3)2)(OC6H3(CH(CH3)2)2)I2

: 1822-00-0
trimethylsilylmethyllithium

: Ti(N(C(CD3)2CH3)C6H3(CH3)2)(OC6H3(CH(CH3)2)2)(CH2Si(CH3)3)I

Conditions

Conditions	Yield
In hexane stirring (-35°C, 20 min); filtering, pptn. on concg.;	100%

: 17599-61-0
N-benzylidene-1,1,1-trimethylsilanamine

: 1822-00-0
trimethylsilylmethyllithium

: 71354-69-3
1-phenyl-2-(trimethylsilyl)ethanamine

Conditions

Conditions	Yield
Stage #1: N-benzylidene-1,1,1-trimethylsilanamine; trimethylsilylmethyllithium In tetrahydrofuran; pentane at 0℃; for 2.16667h; Inert atmosphere; Stage #2: With hydrogenchloride; water In tetrahydrofuran; pentane	100%

: 1822-00-0
trimethylsilylmethyllithium

: 53127-81-4
[(trimethylsilyl)methyl]sodium

Conditions

Conditions	Yield
With sodium t-butanolate In pentane at -35 - 20℃; for 2h;	100%
With sodium t-butanolate In hexane; pentane at 20℃; Inert atmosphere;	86.4%
With sodium t-butanolate In hexane; pentane at 0 - 20℃; Schlenk technique;	82%

: C44H45ClN4Ni

: 1822-00-0
trimethylsilylmethyllithium

: C48H56N4NiSi

Conditions

Conditions	Yield
In pentane; benzene at 20℃; for 0.5h; Cooling;	100%

: 75833-45-3
2,5-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one

: 1822-00-0
trimethylsilylmethyllithium

: 1-trimethylsilylmethyl-3,6-dimethoxybenzocyclobuten-1-ol

Conditions

Conditions	Yield
In tetrahydrofuran; pentane at -78℃; for 0.0833333h;	99%

: 1822-00-0
trimethylsilylmethyllithium

: 175883-01-9
2-<<4-bromo-2-<(tert-butyldimethylsilyl)oxy>-5-methoxyphenyl>methyl>-5,5-dimethylcyclohexan-1-one

: 2-[4-Bromo-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-benzyl]-3,3-dimethyl-1-trimethylsilanylmethyl-cyclohexanol

Conditions

Conditions	Yield
In tetrahydrofuran; pentane at -78℃;	99%

: 1822-00-0
trimethylsilylmethyllithium

: 749888-12-8
1-adamantan-1-yl-2-ethoxy-propenone

: 749888-28-6
2-adamantan-1-yl-3-ethoxy-1-trimethylsilanyl-but-3-en-2-ol

Conditions

Conditions	Yield
Stage #1: trimethylsilylmethyllithium With cerium(III) chloride In toluene; pentane at -78℃; for 1h; Stage #2: 1-adamantan-1-yl-2-ethoxy-propenone In toluene; pentane at -78℃; for 2h;	99%

: bis(n-butylcyclopentadienyl)hafnium dichloride

: 1822-00-0
trimethylsilylmethyllithium

: (n-BuCp)2Hf(CH2SiMe3)2

Conditions

Conditions	Yield
In toluene at 0 - 20℃; for 5.01667h;	99%

: 392292-96-5
[bis(2,6-diisopropylphenylimino-κN,N'-ethyl)pyridine-κN]CoCl

: 1822-00-0
trimethylsilylmethyllithium

: 404876-80-8
2,6-[2,6-(iPr)2C6H3NCMe]2C5H3NCoCH2SiMe3

Conditions

Conditions	Yield
In toluene N2, standard Schlenk techniques, mixed, stirred for 10 min room temp.; filtered over celite, evapd. to dryness in vac., elem. anal.;	99%

: 182256-01-5
[TaCl3(2,3,5,6-tetraphenylphenoxide)2]

: 1822-00-0
trimethylsilylmethyllithium

: Ta(OC6H(C6H5)4)2(CH2Si(CH3)3)3

Conditions

Conditions	Yield
In benzene 25°C;	99%

: 389123-76-6
[(η(5)-C5H4(CH2)2P(H)(2,4,6-trimethylphenyl)-κP)ZrCl3(tetrahydrothiophene)]

: 1822-00-0
trimethylsilylmethyllithium

: 502966-58-7
[(η(5)-C5H4(CH2)2P(H)(2,4,6-trimethylphenyl))Zr(CH2SiMe3)3]

Conditions

Conditions	Yield
In not given	99%

: 526199-98-4
Sc(C5H4NCCH3(CH2NSi(CH3)3)2)Cl(C4H8O)

: 1822-00-0
trimethylsilylmethyllithium

: 526200-01-1
Sc(C5H4NCCH3(CH2NSi(CH3)3)2)CH2Si(CH3)3(C4H8O)

Conditions

Conditions	Yield
In benzene-d6 the soln. of complex and Li-compound in C6D6 were mixed in NMR tube, 30 min (inert atm.); not sepd., detected by NMR spectra;	99%

: [η(2),η(1)-Me3SiNC(Ph)N(CH2)3NMe]TiCl2

: 1822-00-0
trimethylsilylmethyllithium

: [η(2),η(1)-Me3SiNC(Ph)N(CH2)3NMe]Ti(CH2SiMe3)2

Conditions

Conditions	Yield
In pentane all manipulations under purified N2; pentane condensed into vessel containing solid mixt. of Ti and Li compds., frozen in liq. N2, allowed to warm to -15°C, stirred for 2 h; filtered, extd. with pentane, volatiles removed in vac., recrystd., elem. anal.;	99%

: 314733-86-3
RhCl[2,6-bis(1-(2,6-diisopropylphenyl)iminoethyl)pyridine]

: 1822-00-0
trimethylsilylmethyllithium

: 756876-44-5
[Rh(CH2Si(CH3)3)(C5H3N(C(CH3)N(C6H3(CH(CH3)2)2))2)]

Conditions

Conditions	Yield
In toluene; pentane under inert atm. mixt. Rh complex and Me3SiCH2Li in toluene-pentane was stirred for 24 h; soln. was filtered and dried in vacuo, residue was extd. with hexane, solvent was removed in vacuo;	99%
In toluene; pentane under Ar, Schlenk setup, pentane/toluene soln. of ligand added to metalcompd. (2:1), stirred for 1 d; filtered, evapd.;

: 182256-06-0
TaCl3(OC6H(CH3)2(C6H5)2)2

: 1822-00-0
trimethylsilylmethyllithium

: Ta(CH2Si(CH3)3)3(OC6H(CH3)2(C6H5)2)2

Conditions

Conditions	Yield
In benzene 25°C;	99%

: 116642-99-0
Ta(2,6-diphenylphenoxide)2Cl3

: 1822-00-0
trimethylsilylmethyllithium

: Ta(CH2Si(CH3)3)3(OC6H3(C6H5)2)2

Conditions

Conditions	Yield
In benzene 25°C;	99%

: (N-[2-P(CHMe2)2-4-methylphenyl]2(1-))Ti=CH(t)Bu(triflate)

: 1822-00-0
trimethylsilylmethyllithium

: 871558-40-6
(N-[2-P(CHMe2)2-4-methylphenyl]2(1-))Ti=CDSiMe3(C6D5)

Conditions

Conditions	Yield
In benzene-d6 byproducts: CH3Bu-t; at 40°C for 24 h;	99%

: 1001195-98-7
[ZrCl3(κ3-N2P-(tert-butyl)NSiMe2N(CH2CH2P(i-Pr)2)2)]

: 1822-00-0
trimethylsilylmethyllithium

: [Zr(CH2SiMe3)3((tert-butyl)NSiMe2N(CH2CH2P(i-Pr)2)2)]

Conditions

Conditions	Yield
In toluene byproducts: LiCl; using Schlenk techniques; addn. soln. of LiCH2SiMe3 (3 equiv.) to soln. of ZrCl3((t-Bu)NSiMe2N(CH2CH2P(i-Pr)2)2) in toluene at -40°C; warming to room temp.; stirring for 3 h; removal of volatile material under vac., extn. with pentane; removal of solvent under vac.;	99%

: (E)-2-(2-methoxyethenyl)naphthalene

: 1822-00-0
trimethylsilylmethyllithium

: 623582-16-1
2-[(1E)-3-(trimethylsilyl)-1-propen-1-yl]naphthalene

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0) In toluene; pentane at 60℃; for 2h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Sealed tube; stereospecific reaction;	99%

: 1822-00-0
trimethylsilylmethyllithium

: 52119-18-3
1-(2-naphthalenyl)-1-(trimethylsilyloxy)ethylene

: [2-(naphthalene-2-yl)allyl]trimethylsilane

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0) In toluene; pentane at 60℃; for 2h; Inert atmosphere; Sealed tube; stereospecific reaction;	99%

: 53317-83-2, 14782-78-6
[scandium(III)(chloride)3(tetrahydrofuran)3]

: C11H19BN(1-)*Li(1+)

: 1822-00-0
trimethylsilylmethyllithium

: C23H49BNOScSi2

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.25h;	99%

...Expand

: 93-04-9
2-Methoxynaphthalene

: 1822-00-0
trimethylsilylmethyllithium

: 27016-35-9
trimethyl(naphthalen-2-ylmethyl)silane

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0) In toluene; pentane at 50℃; for 2h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique; Sealed tube;	99%
With bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate; tricyclohexylphosphine In toluene at 80℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox;	76%

: 18410-39-4
(6-methoxynaphthalen-2-yl)trimethylsilane

: 1822-00-0
trimethylsilylmethyllithium

: trimethyl(6-((trimethylsilyl)methyl)naphthalen-2-yl)silane

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0) In toluene; pentane at 50℃; for 2h; Inert atmosphere; Schlenk technique; Sealed tube;	99%

: 59115-45-6
2-(4-methoxyphenyl)naphthalene

: 1822-00-0
trimethylsilylmethyllithium

: trimethyl(4-(naphthalen-2-yl)benzyl)silane

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0) In toluene; pentane at 80℃; for 2h; Inert atmosphere; Schlenk technique; Sealed tube;	99%

: 613-37-6
4-methoxylbiphenyl

: 1822-00-0
trimethylsilylmethyllithium

: 81309-60-6
([1,1'-biphenyl]-4-ylmethyl)trimethylsilane

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0) In toluene; pentane at 80℃; for 2h; Inert atmosphere; Schlenk technique; Sealed tube;	99%

: 28396-55-6
2-(4-chlorophenyl)naphthalene

: 1822-00-0
trimethylsilylmethyllithium

: trimethyl(4-(naphthalen-2-yl)benzyl)silane

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(diphenylphosphino)ethane In toluene; pentane at 80℃; for 2h; Sealed tube; Inert atmosphere;	99%

(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.

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

Product Name

(TRIMETHYLSILYL)METHYLLITHIUM

Synthetic route

(Trimethylsilyl)methyllithium Specification

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