tris(trimethylsilylmethyl)gallium
trimethylamine hydrochloride
A
tetramethylsilane
B
Ga(3+)*2CH2Si(CH3)3(1-)*Cl(1-)*N(CH3)3=Ga(CH2Si(CH3)3)2Cl*N(CH3)3
Conditions | Yield |
---|---|
In benzene under N2 or Ar mixt. in stoich. quantity stirred at room temp. for 2 h; volatile components removed by vac. distn., crude product sublimed at 32°C; elem. anal.; | A 100% B 98.5% |
tris(trimethylsilylmethyl)gallium
A
tetramethylsilane
Conditions | Yield |
---|---|
With HCl under inert gas at 25°C for 12 h with 1:2 GaR3:HCl; vac. sublimation at 50°C; elem. anal.; | A 99.6% B 91% |
tris(trimethylsilylmethyl)gallium
A
tetramethylsilane
Conditions | Yield |
---|---|
With HBr under inert gas at 25°C for 12 h with 1:2 GaR3:HBr; extn. with benzene; | A 99.5% B 94.2% |
tris(trimethylsilylmethyl)gallium
A
tetramethylsilane
B
[Ga(CH2Si(CH3)3)2Br]2
Conditions | Yield |
---|---|
With HBr under inert gas at 25°C for 12 h with 1:1 GaR3:HBr; recrystn. from benzene; | A 99.2% B 94% |
tris(trimethylsilylmethyl)gallium
A
((trimethylsilyl)methyl)gallium(III) chloride
B
tetramethylsilane
Conditions | Yield |
---|---|
With HCl In benzene HCl added in three equimolar portions by vac. distn. at -196°C, after each addn. mixt. warmed to room temp. and stirred for 1 h; volatile products fractionally distd., nonvolatile products extd. with n-pentane, insol. component collected, identified as Ga(CH2SiMe3)2Cl (elem. anal.), sol. fraction mixt. of Ga(CH2SiMe3)Cl2 and Ga(CH2SiMe3)3; | A 50.5% B 99.2% C n/a |
diphenylphosphane
diisopropyl-carbodiimide
A
N,N′-diisopropyl-1,1-diphenylphosphanecarboximidamide
B
tetramethylsilane
Conditions | Yield |
---|---|
With C35H66Si3Y(1-)*C14H30LiO4(1+) In tetrahydrofuran at 80℃; for 1h; Mechanism; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; | A 97% B n/a |
tris{(trimethylsilyl)methyl}indium
diphenylphosphane
A
tetramethylsilane
Conditions | Yield |
---|---|
In pentane byproducts: SiMe4; The reagents in benzene were combined in a reaction tube, evacuated and heated at 55°C for 7 d;; mixt. was cooled to -78°C, filtered, washed with benzene, recrystd. from pentane at -78°C; elem. anal.;; | A 95% B 93% |
In pentane The reagents were combined in a reaction tube, evacuated and heated at 55°C for 3 d;; mixt. was cooled to -78°C, filtered, washed with pentane at -20°C; elem. anal.;; | A n/a B 94% |
Conditions | Yield |
---|---|
With iodine; (3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid Heating; | 92% |
With iodine; (3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid Mechanism; Heating; other permethyloligosiloxanes; | 92% |
Conditions | Yield |
---|---|
In toluene In inert atmosphere, heating of Ru-complex with HSiEt3 (90°C, 9 h).; Evapn. in vac., recrystn. (toluene), elem. anal.; | A n/a B 92% |
(η5-C5Me5)(PMe3)2Ru(CH2SiMe3)
Triethoxysilane
A
tetramethylsilane
C
trimethylphosphane
Conditions | Yield |
---|---|
In inert atmosphere, heating of Ru-complex with HSi(OEt)3 (80°C, 12 h, closed vessel), briefly pumping to remove PMe3, continued heating (80°C, 6 h).; Evapn. in vac. gives a waxy solid, recrystn. (acetone), elem. anal.; | A n/a B 92% C n/a |
Conditions | Yield |
---|---|
With iodine; (3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid Heating; | 90% |
methyltrimethicone
tetramethylsilane
Conditions | Yield |
---|---|
With iodine; (3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid Heating; | 90% |
Conditions | Yield |
---|---|
With iodine; (3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid Heating; | 90% |
Conditions | Yield |
---|---|
With To(M)Rh(CO)2 In benzene at 20℃; for 36h; Inert atmosphere; Irradiation; | 87% |
chloro(trimethylsilyl)methyl lithium
[diphenylmanganese]
A
biphenyl
B
tetramethylsilane
C
benzyltrimethylsilane
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran mixing of MnPh2 with Li-salt in THF (molar ratio 1:2, -78°C, 1 h), rise of temp. to 25°C (over 1 h); gas liquid chromy. after quenching with 2 N HCl; | A 4% B n/a C 82% |
tris{(trimethylsilyl)methyl}indium
A
tetramethylsilane
B
K(1+)*In(CH2Si(CH3)3)3H(1-)=KIn(CH2Si(CH3)3)3H
C
hydrogen
Conditions | Yield |
---|---|
In pentane under N2, pentane added to KH, In-compd. (molar ratio 1:3) added, frozen to -196°C, evacuated, warmed to room temp., stirred for 3 d, opened; filtered, washed with pentane, solvent removed, benzene added, warmed to room temp., filtered, solvent removed by vac. distn.; | A 0% B 80.9% C 0% |
tetra-n-butylammonium nitridotetrakis(trimethylsilylmethyl)ruthenium(VI)
cis-tetra-n-butylammonium nitridodochlorobis(trimethylsilylmethyl)ruthenium(VI)
B
tetramethylsilane
Conditions | Yield |
---|---|
With HCl In toluene bubbling of HCl(g) to the Ru compd. in toluene at room temp. for 1 h; evapn. (vacuum), washing with hexane and recrystn. from toluene-hexane at -30°C; elem. anal.; | A 79% B n/a |
With HCl In diethyl ether addn. of excess of HCl(g) to the Ru compd. in ether under N2 at -78°C, warming to room temp. and stirring for 40-60 min; evapn. (vacuum), washing with hexane and recrystn. from toluene-hexane at -30°C; elem. anal.; | A 71% B n/a |
(η5-C5Me5)(PMe3)2Ru(CH2SiMe3)
diphenylsilyl chloride
A
tetramethylsilane
C
trimethylphosphane
Conditions | Yield |
---|---|
In inert atmosphere, heating of Ru-complex with HSi(Ph2Cl)3 (110°C, 16 h, closed vessel, stirring), periodic pumping to remove PMe3.; Cooling to room temp., addn. of pentane, cooling (-78°C, 6 h), filtn. of pale yellow crystals, washing (pentane, -78°C), drying in vac, elem. anal.; | A n/a B 78% C n/a |
Conditions | Yield |
---|---|
In toluene In inert atmosphere, heating of Ru-complex with HSiEt3 (100°C, 6 h).; Cooling (6 h, -50°C), filtn., drying in vac., elem. anal.; | A n/a B 78% |
chloro(trimethylsilyl)methyl lithium
Dibenzol-chrom(II)
A
biphenyl
B
tetramethylsilane
C
benzyltrimethylsilane
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran mixing of CrPh2 with Li-salt in THF (molar ratio 1:1.5, -78°C, 1 h), rise of temp. to 25°C (over 1 h); gas liquid chromy. after quenching with 2 N HCl; | A n/a B n/a C 76% |
A
tetramethylsilane
Conditions | Yield |
---|---|
In benzene kept at room temp. for 7 d; removal of solvent, dissoln. in pentane and cooled to -10°C; | A n/a B 76% |
chloro(trimethylsilyl)methyl lithium
Diphenylkobalt
A
biphenyl
B
tetramethylsilane
C
benzyltrimethylsilane
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran mixing of CoPh2 with Li-salt in THF (molar ratio 1:1.5, -78°C, 1 h), rise of temp. to 25°C (over 1 h); gas liquid chromy. after quenching with 2 N HCl; | A 70% B n/a C 12% |
chloro(trimethylsilyl)methyl lithium
A
tetramethylsilane
B
(4,4'-dimethyl-1,1'-biphenyl)
C
1-((trimethylsilyl)methyl)-4-methylbenzene
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran mixing of Zr-complex with Li-salt in THF (molar ratio 1:1, -78°C, 1 h), rise of temp. to 25°C (over 1 h); gas liquid chromy. after quenching with 2 N HCl; | A n/a B n/a C 70% |
{(C5H5)2Nb(CH2Si(CH3)3)Cl}(1+)*PF6(1-)={(C5H5)2Nb(CH2Si(CH3)3)Cl}PF6
A
tetramethylsilane
B
Hexamethyldisiloxane
Conditions | Yield |
---|---|
With H2O In [(2)H6]acetone 1 equiv. of H2O in acetone-d6; not isolated; detected by NMR and GC; | A <5 B 70% |
Conditions | Yield |
---|---|
In further solvent(s) In inert atmosphere, refluxing of Ru-complex in HSiEt3 (5 h).; Evapn. of yellow soln. to dryness, dissolving (pentane), concg., cooling (-40°C), elem. anal.; | A n/a B 68% |
chloro(trimethylsilyl)methyl lithium
A
biphenyl
B
tetramethylsilane
C
benzyltrimethylsilane
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran mixing of Hf-complex with Li-salt in THF (molar ratio 1:1.3, -78°C, 1 h), rise of temp. to 25°C (over 1 h); gas liquid chromy. after quenching with 2 N HCl; | A 2% B n/a C 65% |
chloro(trimethylsilyl)methyl lithium
A
biphenyl
B
tetramethylsilane
C
benzyltrimethylsilane
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran mixing of (Et3P)2NiPh2 with Li-salt in THF (molar ratio 1:1.5, -78°C, 1 h), rise of temp. to 25°C (over 1 h); gas liquid chromy. after quenching with 2 N HCl; | A 65% B n/a C 9% |
octamethylcyclotetrasiloxane
A
tetramethylsilane
B
trimethylsilyl iodide
C
Hexamethyldisiloxane
D
tetradecamethylhexasiloxane
Conditions | Yield |
---|---|
With gallium(III) iodide at 140 - 170℃; for 5h; Yields of byproduct given; | A 61% B n/a C n/a D n/a |
With gallium(III) iodide at 140 - 170℃; for 5h; Title compound not separated from byproducts; | A 61% B n/a C n/a D n/a |
With gallium(III) iodide at 140 - 170℃; for 5h; Yield given; Title compound not separated from byproducts; | A 61% B n/a C n/a D n/a |
octamethylcyclotetrasiloxane
A
tetramethylsilane
B
trimethylsilyl iodide
C
Hexamethyldisiloxane
D
dodecamethyl-cyclohexasiloxane
Conditions | Yield |
---|---|
With gallium(III) iodide at 140 - 170℃; for 5h; Yield given; Title compound not separated from byproducts; | A 61% B n/a C n/a D n/a |
octamethylcyclotetrasiloxane
A
tetramethylsilane
B
trimethylsilyl iodide
C
Hexamethyldisiloxane
D
hexadecamethylheptasiloxane
Conditions | Yield |
---|---|
With gallium(III) iodide at 140 - 170℃; for 5h; Yield given; Title compound not separated from byproducts; | A 61% B n/a C n/a D n/a |
Conditions | Yield |
---|---|
With 1,2-dichloro-ethane; aluminium trichloride at 130℃; for 17h; | 100% |
With hydrogenchloride; aluminium trichloride | |
With chlorine; iodine In tetrachloromethane at 30℃; | |
With hydrogenchloride |
tetramethylsilane
germaniumtetrachloride
A
chloro-trimethyl-silane
B
chlorotrimethylgermane
C
tetramethylgermane
Conditions | Yield |
---|---|
aluminium bromide In neat (no solvent) molar ratio Me4Si/GeCl4 = 2/1, at 180°C for 2.75 h, cooled; NMR, mass spectra, chromy.; | A 100% B 18% C 82% |
aluminium bromide In neat (no solvent) molar ratio Me4Si/GeCl4 = 2/1, at 180°C for 4.5 h, cooled; NMR, mass spectra, chromy.; | A 100% B 23% C 77% |
aluminium bromide In neat (no solvent) molar ratio Me4Si/GeCl4 = 2/1, at 200°C for 3.5 h, cooled; NMR, mass spectra, chromy.; | A 100% B 13% C 87% |
tetramethylsilane
germaniumtetrachloride
A
chloro-trimethyl-silane
B
chlorotrimethylgermane
C
dimethylsilicon dichloride
Conditions | Yield |
---|---|
aluminium bromide In neat (no solvent) molar ratio Me4Si/GeCl4 = 2/1, at 200°C for 15 h, cooled; NMR, mass spectra, chromy.; | A 50% B 100% C 50% |
tetramethylsilane
germaniumtetrachloride
A
methyltrichlorogermane
B
dimethylsilicon dichloride
C
dichlorodimethylgermanium
Conditions | Yield |
---|---|
aluminium bromide In neat (no solvent) molar ratio Me4Si/GeCl4 = 0.5/1, at 200°C for 28 h, cooled; NMR, mass spectra, chromy.; | A 64% B 100% C 36% |
tetramethylsilane
germaniumtetrachloride
A
chlorotrimethylgermane
B
dimethylsilicon dichloride
C
dichlorodimethylgermanium
Conditions | Yield |
---|---|
aluminium bromide In neat (no solvent) molar ratio Me4Si/GeCl4 = 1/1, at 200°C for 56 h, cooled; NMR, mass spectra, chromy.; | A 14% B 100% C 86% |
tetramethylsilane
trifluorormethanesulfonic acid
trimethylsilyl trifluoromethanesulfonate
Conditions | Yield |
---|---|
for 1h; Ambient temperature; | 99% |
Conditions | Yield |
---|---|
reaction at 70°C for 2 days; | 99% |
Conditions | Yield |
---|---|
With bis(chlorosulfonyl)amine In dichloromethane at 30℃; for 18h; Yields of byproduct given; | A n/a B 97% |
tetramethylsilane
Cyclopentane
carbon monoxide
1-cyclopentylethanone
Conditions | Yield |
---|---|
With aluminum tri-bromide; 1,2-dibromomethane In tetrachloromethane at 0℃; | 97% |
Conditions | Yield |
---|---|
In diethyl ether (inert gas); GaCl3 and SiMe4 is stirred under high vacuum, heated to 70-80°C, evapn. of the volatiles, residue is dissolved in Et2O, cooled to 0°C, dropwise addn. of the Li-salt in Et2O and after various steps addn. of the Co-complex; filtration, evapn. of the solvent, elem. anal.; | 96% |
tetramethylsilane
Conditions | Yield |
---|---|
at 85℃; for 9h; Sealed tube; Glovebox; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane for 4h; Ambient temperature; | 95% |
tetramethylsilane
germaniumtetrachloride
A
chloro-trimethyl-silane
B
chlorotrimethylgermane
C
methyltrichlorogermane
D
dimethylsilicon dichloride
E
dichlorodimethylgermanium
Conditions | Yield |
---|---|
aluminium bromide In neat (no solvent) molar ratio Me4Si/GeCl4 = 1/1, at 200°C for 22 h, cooled; NMR, mass spectra, chromy.; | A 6% B 30% C 15% D 94% E 56% |
aluminium bromide In neat (no solvent) molar ratio Me4Si/GeCl4 = 0.5/1, at 200°C for 6 h, cooled; NMR, mass spectra, chromy.; | A 26% B 33% C 30% D 74% E 37% |
aluminium bromide In neat (no solvent) molar ratio Me4Si/GeCl4 = 1/1, at 200°C for 6 h, cooled; NMR, mass spectra, chromy.; | A 60% B 54% C 11% D 40% E 35% |
Conditions | Yield |
---|---|
With hydrogenchloride; aluminium trichloride In dichloromethane at 20℃; for 1h; | 92% |
tetramethylsilane
perfluorobutanesulfonic acid
Nonafluorobutansulfonsaeure-trimethylsilylester
Conditions | Yield |
---|---|
10°C; | 92% |
tetramethylsilane
1,3,5-trisbromobenzene
3,5-dibromo-1-trimethylsilylbenzene
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 0.25h; Inert atmosphere; Stage #2: tetramethylsilane In tetrahydrofuran; hexane; toluene at -78 - 20℃; Inert atmosphere; | 92% |
tetramethylsilane
germaniumtetrachloride
A
chloro-trimethyl-silane
B
chlorotrimethylgermane
C
tetramethylgermane
D
dimethylsilicon dichloride
Conditions | Yield |
---|---|
aluminium bromide In neat (no solvent) molar ratio Me4Si/GeCl4 = 4/1, at 200°C for 8 h, cooled; NMR, mass spectra, chromy.; | A 91% B 60% C 40% D 9% |
aluminium bromide In neat (no solvent) molar ratio Me4Si/GeCl4 = 0.33/1, at 200°C for 5 h, cooled; NMR, mass spectra, chromy.; | A 89% B 74% C 26% D 11% |
aluminium bromide In neat (no solvent) molar ratio Me4Si/GeCl4 = 3/1, at 200°C for 21 h, cooled; NMR, mass spectra, chromy.; | A 80% B 80% C 20% D 20% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; calcium hydride at 55℃; for 5h; Inert atmosphere; | 90.6% |
The Tetramethylsilane, with the CAS registry number 75-76-3, is also known as Silane, tetramethyl-. It belongs to the product categories of Organics; Analytical Chemistry; NMR Spectrometry; Si (Classes of Silicon Compounds); Si-(C)4 Compounds; Standards for NMR; Alkyl Silanes; Organometallic Reagents; Organosilicon; Others Vapor Deposition Precursors; Precursors by Metal; NMR Reference Standards Alphabetic; NMR Stable Isotopes; NMR Organometallic Reagents; Analytical Standards; Others Alphabetic; Spectroscopy; TA - TE. Its EINECS registry number is 200-899-1. This chemical's molecular formula is C4H12Si and molecular weight is 88.22. Its IUPAC name is called tetramethylsilane. What's more, the product should be sealed and stored in cool, dry and well-ventilated place. TMS is a building block in organometallic chemistry but also finds use in diverse niche applications.
Physical properties of Tetramethylsilane: (1)ACD/LogP: 2.84; (2)ACD/LogD (pH 5.5): 2.84; (3)ACD/LogD (pH 7.4): 2.84; (4)ACD/BCF (pH 5.5): 84.26; (5)ACD/BCF (pH 7.4): 84.26; (6)ACD/KOC (pH 5.5): 831.72; (7)ACD/KOC (pH 7.4): 831.72; (8)Index of Refraction: 1.367; (9)Molar Refractivity: 29.29 cm3; (10)Molar Volume: 130.2 cm3; (11)Surface Tension: 13.6 dyne/cm; (12)Density: 0.677 g/cm3; (13)Enthalpy of Vaporization: 26.15 kJ/mol; (14)Boiling Point: 26.8 °C at 760 mmHg; (15)Vapour Pressure: 713 mmHg at 25°C.
Preparation of Tetramethylsilane: this chemical is a by-product of the production of methyl chlorosilanes, SiClx(CH3)4-x, via the direct process of reacting methyl chloride with silicon. The more useful products of this reaction are those for x = 1, 2, and 3.
Uses of Tetramethylsilane: it undergoes deprotonation upon treatment with butyllithium to give (H3C)3SiCH2Li. The latter, trimethylsilylmethyl lithium, is a relatively common alkylating agent. Tetramethylsilane is the accepted internal standard for calibrating chemical shift for 1H, 13C and 29Si NMR spectroscopy in organic solvents (where TMS is soluble). In water, where it is not soluble,sodium salts of DSS, 2,2-dimethyl-2-silapentane-5-sulfonate, is used instead. Because of its high volatility, TMS can easily be evaporated, which is convenient for recovery of samples analyzed by NMR spectroscopy.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. extremely flammable. It is harmful by inhalation and if swallowed. In addition, it is irritating to skin. You should keep it away from sources of ignition - No smoking. Whenever you will contact it, please wear suitable protective clothing. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C[Si](C)(C)C
(2)InChI: InChI=1S/C4H12Si/c1-5(2,3)4/h1-4H3
(3)InChIKey: CZDYPVPMEAXLPK-UHFFFAOYSA-N
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