Conditions | Yield |
---|---|
With amorphous silicon In hexane at 20℃; Temperature; Solvent; Inert atmosphere; Schlenk technique; Cooling with ice; | 98% |
With nickel(II) sulphate; tetrachlorosilane; trichlorosilane In tetrachloromethane at 55 - 60℃; for 3h; Large scale; | 96.8% |
Stage #1: methanol With iodine; silicon tetrafluoride; aluminium at 37℃; for 2.5h; Stage #2: at 40℃; for 2.5h; Reflux; | 86% |
methanol
silicon tetrafluoride
magnesium
B
tetramethylorthosilicate
Conditions | Yield |
---|---|
Stage #1: methanol; magnesium With iodine at 20℃; for 1.5h; Inert atmosphere; Reflux; Stage #2: silicon tetrafluoride Inert atmosphere; Stage #3: at 300℃; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; Calcination; | A 98% B 85% |
Stage #1: methanol; magnesium at 20℃; for 3h; Stage #2: silicon tetrafluoride at 20℃; for 0.5h; Temperature; |
Conditions | Yield |
---|---|
With CH3OH; NH3 In methanol introduction of NH3 into CH3OH in absence of air; introduction of SiF4;; filtration; distn. of the filtrate;; | A n/a B 95% |
With methanol; ammonia In methanol introduction of NH3 into CH3OH in absence of air; introduction of SiF4;; filtration; distn. of the filtrate;; | A n/a B 95% |
(morpholinomethyl)hydrosilane
methanol
A
4-methyl-morpholine
B
tetramethylorthosilicate
C
α-morpholine methyltrimethoxysilane
Conditions | Yield |
---|---|
In neat (no solvent) at 0 - 5℃; for 5h; Mechanism; Inert atmosphere; | A 5.5% B 5.5% C 90% |
Conditions | Yield |
---|---|
SiCl4 and a small excess of methylnitrite in absence of moisture under cooling; slow heating at about 120°C;; | 80% |
tetrachlorosilane
tetramethylorthosilicate
Conditions | Yield |
---|---|
With methanol In methanol fast addn. of SiCl4 to a small excess of CH3OH (ice bath);; fractional distn.;; | 80% |
With CH3OH SiCl4 and CH3OH in presence of CH3COONa;; | 80% |
With CH3OH In methanol fast addn. of SiCl4 to a small excess of CH3OH (ice bath);; fractional distn.;; | 80% |
Conditions | Yield |
---|---|
Stage #1: methanol With Hexafluoropropene oxide at 20℃; Stage #2: triethanolamine In methanol for 1h; | A n/a B 71% |
Conditions | Yield |
---|---|
With copper(l) chloride; silicon at 250℃; under 159611 Torr; for 3h; Temperature; Pressure; Autoclave; | A 70% B n/a |
Conditions | Yield |
---|---|
With methanol In neat (no solvent) heating of Si at 1050°C in H2-atm. for 2 h in presence of Cu-oxide, Cu-halide or Cu-nitrate; dropwise addn. of CH3OH at 300°C;; | 50% |
With methanol; copper In neat (no solvent) heating of Cu and Si at 1050°C in H2-atm. for 2 h; dropwise addn. of CH3OH at 300°C;; | 50% |
With CH3OH; copper In neat (no solvent) heating of Cu and Si at 1050°C in H2-atm. for 2 h; dropwise addn. of CH3OH at 300°C;; | 50% |
Conditions | Yield |
---|---|
With hydrogenchloride | 38% |
Conditions | Yield |
---|---|
With amorphous silicon In paraffin oil at 300℃; for 6h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique; | A 24% B 21% |
With copper; silicon at 259.9℃; under 742.6 Torr; for 5h; Product distribution; preheating at 623 K for 3 h; other reaction times, temperatures, and partial pressures; | |
With copper(l) chloride; silicon at 219.9℃; under 442.5 Torr; Kinetics; temperature- and pressure dependence; |
methanol
A
trimethoxysilane
B
tetramethylorthosilicate
C
dimethoxysilane
D
(dimethoxy)methylsilane
Conditions | Yield |
---|---|
With thiophene; silicon grains; copper(l) chloride at 379.85℃; under 315.025 Torr; | A n/a B n/a C n/a D 10% |
With thiophene; silicon grains; copper(l) chloride at 379.85 - 449.85℃; under 315.025 Torr; for 3h; |
methanol
tetraisocyanatosilane
A
tetramethylorthosilicate
B
silicon dimethoxy diisocyanate
C
silicon trimethoxy isocyanate
D
silicon methoxy triisocyanate
Conditions | Yield |
---|---|
at 25℃; |
Conditions | Yield |
---|---|
With tetrachlorosilane dann Erhitzen auf 120grad; |
phosphoric acid dimethyl ester-trimethoxysilanyl ester
tetramethylorthosilicate
Conditions | Yield |
---|---|
beim Erwaermen im Hochvakuum; |
(vinyl)trimethoxylsilane
(dimethoxymethyl)trimethoxysilane
A
tetramethylorthosilicate
Conditions | Yield |
---|---|
at 125℃; |
(Z)-2-Butene
(dimethoxymethyl)trimethoxysilane
A
tetramethylorthosilicate
B
r-1-methoxy-c-2,c-3-dimethylcyclopropane
C
r-1-methoxy-t-2,-t-3-dimethylcyclopropane
Conditions | Yield |
---|---|
at 125℃; |
2,3-Dimethyl-2-butene
(dimethoxymethyl)trimethoxysilane
A
tetramethylorthosilicate
B
ether, methyl 2,2,3,3-tetramethylcyclopropyl
Conditions | Yield |
---|---|
at 125℃; |
trans-2-Butene
(dimethoxymethyl)trimethoxysilane
A
tetramethylorthosilicate
r-1-methoxy-c-2,t-3-dimethylcyclopropane
Conditions | Yield |
---|---|
at 125℃; |
(dimethoxymethyl)trimethoxysilane
A
tetramethylorthosilicate
B
trimethoxy(methoxymethyl)silane
Conditions | Yield |
---|---|
With trimethoxysilane at 125℃; |
(dimethoxymethyl)trimethoxysilane
cyclohexene
A
tetramethylorthosilicate
B
exo-7-Methoxynorcaran
Conditions | Yield |
---|---|
at 125℃; |
methanol
trimethyl orthoformate
A
tetramethylorthosilicate
B
(dimethoxymethyl)trimethoxysilane
C
Bis--methoxy-methan
Conditions | Yield |
---|---|
With hexachlorodisilane |
(acetoxy)tri(methoxy)silane
A
tetramethylorthosilicate
B
(diacetoxy)(dimethoxy)silane
Conditions | Yield |
---|---|
Product distribution; Ambient temperature; prolonged storage; also heating; |
A
tetramethylorthosilicate
B
4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on
Conditions | Yield |
---|---|
With methanol; sodium hydroxide for 12h; Ambient temperature; Yield given; |
Conditions | Yield |
---|---|
With potassium hydroxide; silica gel at 226.9 - 326.9℃; under 720.06 Torr; Mechanism; | |
With potassium hydroxide; silica gel at 426.9℃; under 720.06 Torr; for 4.5h; |
sodium methylate
3-Chloropropyltrimethoxysilan
A
tetramethylorthosilicate
B
allyltrimethoxysilane
Conditions | Yield |
---|---|
at 190℃; Product distribution; other methoxides, var. temperature; substitution versus elimination products; |
methanol
ethene
A
trimethoxysilane
B
tetramethylorthosilicate
C
ethyltrimethoxysilane
D
ethyl dimethoxy silane
Conditions | Yield |
---|---|
With copper(l) chloride; silicon In toluene at 159.9℃; under 3040 Torr; for 3h; Product distribution; Mechanism; also ethanol; other solvents; effect of the amount of methanol on the silicon conversion and selectivity for organomethoxysilanes; var. pressures, times and temperatures; |
Conditions | Yield |
---|---|
byproducts: SiF(OCH3)3; | 100% |
L-enterobactin
tetramethylorthosilicate
Conditions | Yield |
---|---|
In methanol at 20℃; for 24h; | 100% |
tetramethylorthosilicate
1-amino-3-methylbenzene
benzoic acid
A
benzoic acid methyl ester
B
3'-methylbenzanilide
Conditions | Yield |
---|---|
In toluene at 110℃; for 24h; Molecular sieve; Inert atmosphere; | A 27% B 100% |
tetramethylorthosilicate
C30H27N3O14
Conditions | Yield |
---|---|
In methanol at 20℃; for 24h; | 100% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 24h; | 100% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride at 80℃; for 0.5h; | 99% |
Conditions | Yield |
---|---|
Stage #1: 7-Azaindole With n-butyllithium In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Cooling with ice; Stage #2: tetramethylorthosilicate In tetrahydrofuran at 0 - 20℃; for 8h; Inert atmosphere; | 98% |
tetramethylorthosilicate
carbon dioxide
aniline
N-phenyl methyl carbamate
Conditions | Yield |
---|---|
With di(n-butyl)tin oxide In toluene at 135℃; under 52505.3 Torr; for 5.1h; Reagent/catalyst; Glovebox; Autoclave; | 98% |
With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate In acetonitrile at 150℃; under 37503.8 Torr; for 24h; Catalytic behavior; Mechanism; Reagent/catalyst; Temperature; Pressure; Autoclave; Inert atmosphere; Ionic liquid; Green chemistry; chemoselective reaction; | 92% |
With 1,10-Phenanthroline; zinc diacetate In acetonitrile at 150℃; under 37503.8 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Autoclave; Green chemistry; chemoselective reaction; | 84 %Chromat. |
With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate In acetonitrile at 150℃; under 37503.8 Torr; for 24h; Reagent/catalyst; Temperature; Pressure; Solvent; Autoclave; Sealed tube; | 96 %Chromat. |
tetramethylorthosilicate
Conditions | Yield |
---|---|
Stage #1: 1-isopropyldecahydro quinoxaline With n-butyllithium In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Cooling with ice; Stage #2: tetramethylorthosilicate In tetrahydrofuran at 0 - 20℃; for 8h; Inert atmosphere; | 97.7% |
Conditions | Yield |
---|---|
Stage #1: C15H28N2 With n-butyllithium In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Cooling with ice; Stage #2: tetramethylorthosilicate In tetrahydrofuran at 0 - 20℃; for 6h; Inert atmosphere; | 97.5% |
Conditions | Yield |
---|---|
Stage #1: C15H16N2 With n-butyllithium In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Cooling with ice; Stage #2: tetramethylorthosilicate In tetrahydrofuran at 0 - 20℃; for 6h; Inert atmosphere; | 97.1% |
tetramethylorthosilicate
4-nitrobenzaldehdye
4-nitrobenzoic acid methyl ester
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; (t-Bu2POH)2PdCl2 In acetonitrile at 50℃; for 24h; | 97% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; (t-Bu2POH)2PdCl2 In acetonitrile at 50℃; for 24h; | 97% |
tetramethylorthosilicate
carbon dioxide
cyclohexylamine
cyclohexyl-carbamic acid methyl ester
Conditions | Yield |
---|---|
With di(n-butyl)tin oxide In toluene at 135℃; under 52505.3 Torr; Glovebox; Autoclave; | 97% |
With 1,10-Phenanthroline; zinc diacetate In acetonitrile at 150℃; under 37503.8 Torr; for 24h; Inert atmosphere; Autoclave; Green chemistry; chemoselective reaction; | 80% |
With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate In acetonitrile at 150℃; under 37503.8 Torr; for 24h; Autoclave; Inert atmosphere; Ionic liquid; Green chemistry; chemoselective reaction; | 76% |
tetramethylorthosilicate
carbon dioxide
4-methoxy-aniline
methyl N-(4-methoxyphenyl)carbamate
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; zinc diacetate In acetonitrile at 150℃; under 37503.8 Torr; for 24h; Inert atmosphere; Autoclave; Green chemistry; chemoselective reaction; | 96% |
With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate In acetonitrile at 150℃; under 37503.8 Torr; for 24h; Autoclave; Inert atmosphere; Ionic liquid; Green chemistry; chemoselective reaction; | 96% |
With potassium carbonate In acetonitrile at 150℃; under 37503.8 Torr; for 24h; Autoclave; Sealed tube; | 91% |
With di(n-butyl)tin oxide In toluene at 135℃; under 52505.3 Torr; for 5.1h; Glovebox; Autoclave; | 71% |
tetramethylorthosilicate
Hexamethyldisiloxane
A
1,1,1,5,5,5-hexamethyl-3-trimethylsiloxy-3-hydroxytrisiloxane
B
1,1,1,5,5,5-hexamethyl-3,3-bis(trimethylsiloxy)trisiloxane
C
1,1,1,5,5,5-hexamethyl-3-trimethylsiloxy-3-methoxytrisiloxane
Conditions | Yield |
---|---|
Stage #1: Hexamethyldisiloxane With methanol; sulfuric acid at 5 - 10℃; for 1h; Stage #2: tetramethylorthosilicate at 5 - 10℃; for 1.5h; Stage #3: With sulfuric acid; water more than 3 stages; | A n/a B 94.5% C n/a |
tetramethylorthosilicate
hexanal
allyl-trimethyl-silane
4-methoxy-1-nonene
Conditions | Yield |
---|---|
trimethylsilyl iodide In dichloromethane 1.) -78 deg C, 15 min, 2.) 0 deg C, 3 h; | 94% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride at 80℃; for 2h; | 94% |
tetramethylorthosilicate
2,4-Difluoronitrobenzene
2,4-dimethoxynitrobenzene
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride at 80℃; for 2h; | 94% |
Conditions | Yield |
---|---|
With 1-bromo-butane; magnesium for 5h; Inert atmosphere; Reflux; | 93.43% |
IUPAC Name: Tetramethyl silicate
Empirical Formula: C4H12O4Si
Molecular Weight: 152.2212
Canonical SMILES: CO[Si](OC)(OC)OC
InChI: InChI=1S/C4H12O4Si/c1-5-9(6-2,7-3)8-4/h1-4H3
InChIKey: LFQCEHFDDXELDD-UHFFFAOYSA-N
EINECS: 211-656-4
Product Categories: Silicate; Organics; Si (Classes of Silicon Compounds); Si-O Compounds; Tetraalkoxysilanes; Crosslinkers; Crosslinking Agents; Orthosilicate
Appearance: colourless liquid
Melting point: 4-5 °C
Solubility in water: organic solvents
storage temp.: Flammables area
Sensitive: Moisture Sensitive
Index of Refraction: 1.382
Molar Refractivity: 36.27 cm3
Molar Volume: 155.7 cm3
Surface Tension: 19.9 dyne/cm
Density: 0.977 g/cm3
Flash Point: 28.9 °C
Enthalpy of Vaporization: 34.44 kJ/mol
Boiling Point: 121.2 °C at 760 mmHg
Vapour Pressure of Methyl silicate (CAS NO.681-84-5): 17.7 mmHg at 25 °C
In organic synthesis, Methyl silicate (CAS NO.681-84-5) has been used to convert ketones and aldehydes to the corresponding ketals and acetals, respectively.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mammal (species unspecified) | LD50 | oral | 1gm/kg (1000mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974. | |
mouse | LCLo | inhalation | 1gm/m3/10M (1000mg/m3) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE MUSCULOSKELETAL: OTHER CHANGES | National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. NDCrc-132, Pg. MAY1942, |
mouse | LD50 | intraperitoneal | 250mg/kg (250mg/kg) | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 2, Pg. 56, 1950. | |
rabbit | LD50 | skin | 17mL/kg (17mL/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951. | |
rabbit | LDLo | intravenous | 100mg/kg (100mg/kg) | LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | "Dangerous Properties of Industrial Materials," Sax, N.I., New York, Van Nostrand Reinhold, 1980Vol. 3, Pg. 935, 1968. |
rat | LCLo | inhalation | 250ppm/4H (250ppm) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951. | |
rat | LD50 | intraperitoneal | 100mg/kg (100mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1222, 1986. | |
rat | LDLo | oral | 700mg/kg (700mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | "Dangerous Properties of Industrial Materials," Sax, N.I., New York, Van Nostrand Reinhold, 1980Vol. 3, Pg. 935, 1968. |
Reported in EPA TSCA Inventory.
Poison by intraperitoneal route. Moderately toxic by inhalation. Mildly toxic by skin contact. A severe eye irritant. This material can cause extensive necrosis (experimentally), keratoconus, and opaque cornea. It also causes severe human eye injuries, as well as necrosis of corneal cells, which progresses long after exposure has ceased. It is destructive and its effects resist treatment. Permanent blindness is possible from exposure to it. The kidney seems to be most subject to injury regardless of the mode of exposure. Pulmonary edema has also occurred. This material is more toxic than either ethyl silicate or silicic acid, although it has been thought that the injury caused is largely due to the action of the silicic acid. Flammable when exposed to heat or flame; can react vigorously with oxidizing materials. Potentially violent reaction with metal hexafluorides (e.g., rhenium, molybdenum, tungsten). When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: T+
Risk Statements: 10-26-37/38-41
R10:Flammable.
R26:Very toxic by inhalation.
R37/38:Irritating to respiratory system and skin.
R41:Risk of serious damage to the eyes.
Safety Statements: 16-26-36/37/39-45-28A
S16:Keep away from sources of ignition.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S28:After contact with skin, wash immediately with plenty of soap-suds.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2606 6.1/PG 1
WGK Germany: 3
RTECS: VV9800000
F: 10-21
TSCA: Yes
HazardClass: 6.1
PackingGroup: I
OSHA PEL: TWA 1 ppm
ACGIH TLV: TWA 1 ppm
DOT Classification: 3; Label: Flammable Liquid, Poison
Methyl silicate (CAS NO.681-84-5), its Synonyms are Tetramethoxysilane ; Tetramethyl silicate ; Methyl Silicate 39 ; Methyl orthosilicate ; Silane, tetramethoxy- ; Silicic acid, methyl ester of ortho- ; Silicic acid, tetramethyl ester ; Tetra-methyl orthosilicate .
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