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681-84-5

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681-84-5 Usage

Description

Tetramethyl orthosilicate is the chemical compound with the formula Si(OCH3)4. This molecule consists of four methoxy groups bonded to a silicon atom.Two common organic precursors are tetraethyl orthosilicate (TEOS) and tetramethyl orthosilicate (TMOS). The latter is more toxic than the former.Tetraethyl orthosilicate (TEOS), Si(OC2H5)4, is the first alkoxide of the series, followed by tetramethyl orthosilicate (TMOS), Si(OCH3)4, which is, however, less safe to handle and hydrolyzes faster than TEOS.The hydrolysis of TMOS is, in fact, around six times faster: in general, a lower hydrolysis rate is associated with an increase of the organic group size in the silicon alkoxide. The properties of the silicon alkoxides change according to the dimension of the alkoxy; larger groups produce an increase in molecular weight, viscosity, and boiling point and a decrease in density of the alkoxides.As a rule of thumb, a larger size of the alkoxy group is associated with a lower hydrolysis rate due to the steric hindrance. The reactivity follows the sequence, with tetramethyl orthosilicate the most reactive alkoxide:tetramethyl orthosilicate >tetraethyl orthosilicate>tetra-n-propylorthosilicate>tetrabutyl orthosilicate

Chemical Properties

Tetramethyl orthosilicate (TMOS), the methyl ester of orthosilicic acid, is a colorless, low-viscosity liquid. It is industrially the most important of the tetraalkyl silicates.

Uses

Different sources of media describe the Uses of 681-84-5 differently. You can refer to the following data:
1. Tetramethyl orthosilicate (TMOS) is popularly used in the sol-gel synthesis of silicates1 and chromium-doped silicates and in the formation of hexagonal mesoporous silica layers.
2. Coating screens of television picture tubes; mold binders; corrosion-resistant coatings; catalyst preparation; silicone intermediate
3. Tetramethyl Orthosilicate is a compound used in the research of the multifunctionality of silicified nanoshells and the efficiency at adsorbing cadmium ions at cell interfaces.

Production Methods

Silica aerogels are usually prepared by base-catalyzed reaction of tetramethoxysilane or tetraethoxysilane, mostly with ammonia as the catalyst. A modification of this procedure is to prehydrolyze Si(OR)4 with a small amount of water under acidic conditions.

General Description

A clear colorless liquid. Flash point below 125°F. Less dense than water and insoluble in water. Very toxic by ingestion and inhalation and very irritating to skin and eyes. Used to make paints and lacquers.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

Tetramethyl orthosilicate is incompatible with the following: Oxidizers; hexafluorides of rhenium, molybdenum & tungsten .

Hazard

Eye damage and upper respiratory tract irri-tant.

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Flammability and Explosibility

Flammable

Safety Profile

Poison by intraperitoneal route. Moderately toxic by inhalation. Midly 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.

Potential Exposure

Methyl silicate is used in coating screens of television picture tubes. It may be used in mold binders and in corrosion-resistant coatings; as well as in catalyst preparation and as a silicone intermediate.

Shipping

UN2606 Methyl orthosilicate, Hazard class: 6.1; Labels: 6.1-Poisonous materials, 3-Flammable liquid.

Purification Methods

Purification is as for tetraethoxysilane. It has a vapour pressure of 2.5mm at 0o. [IR: Sternbach & MacDiarmid J Am Chem Soc 81 5109 1959. Beilstein 1 IV 1266.]

Incompatibilities

Vapor may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, including alkaline earth metals, metals, strong acids, strong bases; water, moisture, steam decomposes releasing toxic, flammable gases. Violent reaction with metal hexafluorides of rhenium, molybdenum, and tungsten. Contact with metals may evolve flammable hydrogen gas.

Check Digit Verification of cas no

The CAS Registry Mumber 681-84-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,8 and 1 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 681-84:
(5*6)+(4*8)+(3*1)+(2*8)+(1*4)=85
85 % 10 = 5
So 681-84-5 is a valid CAS Registry Number.
InChI:InChI=1/C2H6O3Si/c1-4-6(3)5-2/h1-2H3

681-84-5 Well-known Company Product Price

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  • Alfa Aesar

  • (L09716)  Tetramethoxysilane, 98%   

  • 681-84-5

  • 25g

  • 134.0CNY

  • Detail
  • Alfa Aesar

  • (L09716)  Tetramethoxysilane, 98%   

  • 681-84-5

  • 100g

  • 372.0CNY

  • Detail
  • Alfa Aesar

  • (L09716)  Tetramethoxysilane, 98%   

  • 681-84-5

  • 500g

  • 1613.0CNY

  • Detail

681-84-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Tetramethyl orthosilicate

1.2 Other means of identification

Product number -
Other names tetramethoxy-silan

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:681-84-5 SDS

681-84-5Synthetic route

methanol
67-56-1

methanol

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
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
67-56-1

methanol

silicon tetrafluoride
7783-61-1

silicon tetrafluoride

magnesium
7439-95-4

magnesium

A

magnesium fluoride

magnesium fluoride

B

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
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;
silicon tetrafluoride
7783-61-1

silicon tetrafluoride

A

ammonium hexafluorosilicate

ammonium hexafluorosilicate

B

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
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
5625-96-7

(morpholinomethyl)hydrosilane

methanol
67-56-1

methanol

A

4-methyl-morpholine
109-02-4

4-methyl-morpholine

B

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

C

α-morpholine methyltrimethoxysilane
154206-90-3

α-morpholine methyltrimethoxysilane

Conditions
ConditionsYield
In neat (no solvent) at 0 - 5℃; for 5h; Mechanism; Inert atmosphere;A 5.5%
B 5.5%
C 90%
tetrachlorosilane
10026-04-7, 53609-55-5

tetrachlorosilane

methyl nitrite
624-91-9

methyl nitrite

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
SiCl4 and a small excess of methylnitrite in absence of moisture under cooling; slow heating at about 120°C;;80%
tetrachlorosilane
10026-04-7, 53609-55-5

tetrachlorosilane

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
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%
methanol
67-56-1

methanol

triethanolamine
102-71-6

triethanolamine

A

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

B

2C6H15NO3*F6Si(2-)*2H(1+)

2C6H15NO3*F6Si(2-)*2H(1+)

Conditions
ConditionsYield
Stage #1: methanol With Hexafluoropropene oxide at 20℃;
Stage #2: triethanolamine In methanol for 1h;
A n/a
B 71%
methanol
67-56-1

methanol

A

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

B

hexamethoxydisiloxane
4371-91-9

hexamethoxydisiloxane

Conditions
ConditionsYield
With copper(l) chloride; silicon at 250℃; under 159611 Torr; for 3h; Temperature; Pressure; Autoclave;A 70%
B n/a
silicon
7440-21-3

silicon

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
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%
methanol
67-56-1

methanol

tris(silatranyloxyethyl)amine
29167-65-5

tris(silatranyloxyethyl)amine

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
With hydrogenchloride38%
methanol
67-56-1

methanol

A

trimethoxysilane
2487-90-3

trimethoxysilane

B

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
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
67-56-1

methanol

A

trimethoxysilane
2487-90-3

trimethoxysilane

B

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

C

dimethoxysilane
5314-52-3

dimethoxysilane

D

(dimethoxy)methylsilane
16881-77-9

(dimethoxy)methylsilane

Conditions
ConditionsYield
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
67-56-1

methanol

tetraisocyanatosilane
3410-77-3

tetraisocyanatosilane

A

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

B

silicon dimethoxy diisocyanate
18147-89-2

silicon dimethoxy diisocyanate

C

silicon trimethoxy isocyanate
18169-84-1

silicon trimethoxy isocyanate

D

silicon methoxy triisocyanate
5578-37-0

silicon methoxy triisocyanate

Conditions
ConditionsYield
at 25℃;
methyl nitrite
624-91-9

methyl nitrite

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
With tetrachlorosilane dann Erhitzen auf 120grad;
phosphoric acid dimethyl ester-trimethoxysilanyl ester
18135-11-0

phosphoric acid dimethyl ester-trimethoxysilanyl ester

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
beim Erwaermen im Hochvakuum;
methanol
67-56-1

methanol

tetraacetoxysilane
562-90-3

tetraacetoxysilane

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

(vinyl)trimethoxylsilane
2768-02-7

(vinyl)trimethoxylsilane

(dimethoxymethyl)trimethoxysilane
22859-33-2

(dimethoxymethyl)trimethoxysilane

A

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

trans-1-Methoxy-2-(trimethoxysilyl)-cyclopropan

trans-1-Methoxy-2-(trimethoxysilyl)-cyclopropan

cis-1-Methoxy-2-(trimethoxysilyl)-cyclopropan

cis-1-Methoxy-2-(trimethoxysilyl)-cyclopropan

Conditions
ConditionsYield
at 125℃;
(Z)-2-Butene
590-18-1

(Z)-2-Butene

(dimethoxymethyl)trimethoxysilane
22859-33-2

(dimethoxymethyl)trimethoxysilane

A

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

B

r-1-methoxy-c-2,c-3-dimethylcyclopropane
2988-72-9

r-1-methoxy-c-2,c-3-dimethylcyclopropane

C

r-1-methoxy-t-2,-t-3-dimethylcyclopropane
2988-73-0

r-1-methoxy-t-2,-t-3-dimethylcyclopropane

Conditions
ConditionsYield
at 125℃;
2,3-Dimethyl-2-butene
563-79-1

2,3-Dimethyl-2-butene

(dimethoxymethyl)trimethoxysilane
22859-33-2

(dimethoxymethyl)trimethoxysilane

A

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

B

ether, methyl 2,2,3,3-tetramethylcyclopropyl
22859-35-4

ether, methyl 2,2,3,3-tetramethylcyclopropyl

Conditions
ConditionsYield
at 125℃;
trans-2-Butene
624-64-6

trans-2-Butene

(dimethoxymethyl)trimethoxysilane
22859-33-2

(dimethoxymethyl)trimethoxysilane

A

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

r-1-methoxy-c-2,t-3-dimethylcyclopropane
2799-30-6, 2988-72-9, 2988-73-0, 66791-94-4, 116405-11-9

r-1-methoxy-c-2,t-3-dimethylcyclopropane

Conditions
ConditionsYield
at 125℃;
(dimethoxymethyl)trimethoxysilane
22859-33-2

(dimethoxymethyl)trimethoxysilane

A

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

B

trimethoxy(methoxymethyl)silane
22859-36-5

trimethoxy(methoxymethyl)silane

Conditions
ConditionsYield
With trimethoxysilane at 125℃;
(dimethoxymethyl)trimethoxysilane
22859-33-2

(dimethoxymethyl)trimethoxysilane

cyclohexene
110-83-8

cyclohexene

A

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

B

exo-7-Methoxynorcaran
23865-95-4

exo-7-Methoxynorcaran

Conditions
ConditionsYield
at 125℃;
methanol
67-56-1

methanol

trimethyl orthoformate
149-73-5

trimethyl orthoformate

A

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

B

(dimethoxymethyl)trimethoxysilane
22859-33-2

(dimethoxymethyl)trimethoxysilane

C

Bis--methoxy-methan
22859-34-3

Bis--methoxy-methan

Conditions
ConditionsYield
With hexachlorodisilane
(acetoxy)tri(methoxy)silane
13170-06-4

(acetoxy)tri(methoxy)silane

A

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

B

(diacetoxy)(dimethoxy)silane
13170-07-5

(diacetoxy)(dimethoxy)silane

Conditions
ConditionsYield
Product distribution; Ambient temperature; prolonged storage; also heating;
C16H30O4Si

C16H30O4Si

A

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

B

4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on
17283-81-7

4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on

Conditions
ConditionsYield
With methanol; sodium hydroxide for 12h; Ambient temperature; Yield given;
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

Conditions
ConditionsYield
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
124-41-4

sodium methylate

3-Chloropropyltrimethoxysilan
2530-87-2

3-Chloropropyltrimethoxysilan

A

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

B

allyltrimethoxysilane
2551-83-9

allyltrimethoxysilane

C

(3-methoxypropyl)trimethoxysilane

(3-methoxypropyl)trimethoxysilane

D

propenyltrimethoxysilane

propenyltrimethoxysilane

Conditions
ConditionsYield
at 190℃; Product distribution; other methoxides, var. temperature; substitution versus elimination products;
methanol
67-56-1

methanol

ethene
74-85-1

ethene

A

trimethoxysilane
2487-90-3

trimethoxysilane

B

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

C

ethyltrimethoxysilane
5314-55-6

ethyltrimethoxysilane

D

ethyl dimethoxy silane
19753-84-5

ethyl dimethoxy silane

Conditions
ConditionsYield
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;
methanol
67-56-1

methanol

sis2

sis2

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

uranium hexafluoride
7783-81-5

uranium hexafluoride

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

uranium hexamethoxide

uranium hexamethoxide

Conditions
ConditionsYield
byproducts: SiF(OCH3)3;100%
L-enterobactin
28384-96-5

L-enterobactin

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

potassium hydroxide

potassium hydroxide

C30H21N3O15Si(2-)*2K(1+)

C30H21N3O15Si(2-)*2K(1+)

Conditions
ConditionsYield
In methanol at 20℃; for 24h;100%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

benzoic acid
65-85-0

benzoic acid

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

3'-methylbenzanilide
582-77-4

3'-methylbenzanilide

Conditions
ConditionsYield
In toluene at 110℃; for 24h; Molecular sieve; Inert atmosphere;A 27%
B 100%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

C30H27N3O14
1309672-95-4

C30H27N3O14

potassium hydroxide

potassium hydroxide

C30H22N3O14Si(1-)*K(1+)

C30H22N3O14Si(1-)*K(1+)

Conditions
ConditionsYield
In methanol at 20℃; for 24h;100%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

C30H27N3O14

C30H27N3O14

potassium hydroxide

potassium hydroxide

C30H22N3O14Si(1-)*K(1+)

C30H22N3O14Si(1-)*K(1+)

Conditions
ConditionsYield
In methanol at 20℃; for 24h;100%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

para-methoxynitrobenzene
100-17-4

para-methoxynitrobenzene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride at 80℃; for 0.5h;99%
7-Azaindole
271-63-6

7-Azaindole

tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

bis(7-azaindoledimethoxy)silane

bis(7-azaindoledimethoxy)silane

Conditions
ConditionsYield
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
681-84-5

tetramethylorthosilicate

carbon dioxide
124-38-9

carbon dioxide

aniline
62-53-3

aniline

N-phenyl methyl carbamate
2603-10-3

N-phenyl methyl carbamate

Conditions
ConditionsYield
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
681-84-5

tetramethylorthosilicate

1-isopropyldecahydro quinoxaline

1-isopropyldecahydro quinoxaline

bis(decahydroquinoxalinedimethoxy)silane

bis(decahydroquinoxalinedimethoxy)silane

Conditions
ConditionsYield
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%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

C15H28N2

C15H28N2

bis(5-isopropyltetradecahydrophenazinedimethoxy)silane

bis(5-isopropyltetradecahydrophenazinedimethoxy)silane

Conditions
ConditionsYield
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%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

C15H16N2

C15H16N2

bis(5-isopropylphenazine)dimethoxysilane

bis(5-isopropylphenazine)dimethoxysilane

Conditions
ConditionsYield
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
681-84-5

tetramethylorthosilicate

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; (t-Bu2POH)2PdCl2 In acetonitrile at 50℃; for 24h;97%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

benzaldehyde
100-52-7

benzaldehyde

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; (t-Bu2POH)2PdCl2 In acetonitrile at 50℃; for 24h;97%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

carbon dioxide
124-38-9

carbon dioxide

cyclohexylamine
108-91-8

cyclohexylamine

cyclohexyl-carbamic acid methyl ester
5817-68-5

cyclohexyl-carbamic acid methyl ester

Conditions
ConditionsYield
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
681-84-5

tetramethylorthosilicate

carbon dioxide
124-38-9

carbon dioxide

4-methoxy-aniline
104-94-9

4-methoxy-aniline

methyl N-(4-methoxyphenyl)carbamate
14803-72-6

methyl N-(4-methoxyphenyl)carbamate

Conditions
ConditionsYield
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
681-84-5

tetramethylorthosilicate

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

A

1,1,1,5,5,5-hexamethyl-3-trimethylsiloxy-3-hydroxytrisiloxane
17477-97-3

1,1,1,5,5,5-hexamethyl-3-trimethylsiloxy-3-hydroxytrisiloxane

B

1,1,1,5,5,5-hexamethyl-3,3-bis(trimethylsiloxy)trisiloxane
3555-47-3

1,1,1,5,5,5-hexamethyl-3,3-bis(trimethylsiloxy)trisiloxane

C

1,1,1,5,5,5-hexamethyl-3-trimethylsiloxy-3-methoxytrisiloxane
56120-91-3

1,1,1,5,5,5-hexamethyl-3-trimethylsiloxy-3-methoxytrisiloxane

Conditions
ConditionsYield
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
681-84-5

tetramethylorthosilicate

hexanal
66-25-1

hexanal

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

4-methoxy-1-nonene
90246-13-2

4-methoxy-1-nonene

Conditions
ConditionsYield
trimethylsilyl iodide In dichloromethane 1.) -78 deg C, 15 min, 2.) 0 deg C, 3 h;94%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

4-fluorobenzonitrile
1194-02-1

4-fluorobenzonitrile

4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride at 80℃; for 2h;94%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

2,4-Difluoronitrobenzene
446-35-5

2,4-Difluoronitrobenzene

2,4-dimethoxynitrobenzene
4920-84-7

2,4-dimethoxynitrobenzene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride at 80℃; for 2h;94%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

di(2-propenyl)dimethoxysilane

di(2-propenyl)dimethoxysilane

Conditions
ConditionsYield
With 1-bromo-butane; magnesium for 5h; Inert atmosphere; Reflux;93.43%

681-84-5Related news

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Silica aerogels with high optical transparency and ultra-low thermal conductivity are ideal candidates for energy-saving windows. Often such applications require rather exquisite control of microstructure (i.e., cluster size and cluster packing geometry). In this research, a series of silica aer...detailed

681-84-5Relevant articles and documents

Direct Transformation of Silica into Alkoxysilanes by Gas-Solid Reactions

Suzuki, Eiichi,Akiyama, Masanari,Ono, Yoshio

, p. 136 - 137 (1992)

Silica gel is conveniently and efficiently converted into tetramethoxysilane by treatment with gaseous dimethyl carbonate at 500-600 K in the presence of an alkali hydroxide catalyst supported on the reacting silica.

The study of an alcoholysis reaction of silicon tetrafluoride with alcohols and magnesium to prepare tetraalkoxysilanes and magnesium fluoride

Zhang, Zongfan,Huang, Zhong,Tian, Qiang,Li, Yuye,Li, Xia,Liang, Xuesong,Du, Lusha

, p. 567 - 573 (2015)

An efficient alcoholysis reaction of silicon tetrafluoride with alcohols in the presence of magnesium can directly prepare tetraalkoxysilane and magnesium fluoride. The reaction can afford tetraethoxysilane, tetramethoxysilane, and magnesium fluoride in good yields with the aid of a catalytic amount of iodine.

-

Rochow

, p. 2170 (1948)

-

Mechanochemistry-a new powerful green approach to the direct synthesis of alkoxysilanes

Temnikov, Maxim N.,Anisimov, Anton A.,Zhemchugov, Pavel V.,Kholodkov, Dmitry N.,Goloveshkin, Alexander S.,Naumkin, Alexander V.,Chistovalov, Sergey M.,Katsoulis, Dimitris,Muzafarov, Aziz M.

, p. 1962 - 1969 (2018)

The present work shows a new one-stage mechanochemical method for the direct synthesis of alkoxysilanes by silicon mechanoactivation followed by a reaction with an alcohol. Alkoxysilanes were obtained with nearly complete silicon and alcohol conversion. This method allows for a considerable simplification of the traditional multistage process by eliminating three stages that include silicon and catalyst preparation, and adapts it to green chemistry requirements. Vibration milling removed the oxide film, and the mechanoactivation of the large silicon fraction (1000-2000 μm) occurs in the reactor working space. Abrasion of the reactor walls and grinding bodies made of brass results in a developed catalytic surface on silicon, as it has been proven by a set of physical analytical methods such as scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), powder X-ray diffraction (PXRD), and X-ray photoelectron spectroscopy (XPS).

Method for preparing organosilane by utilizing organosilicone byproduct

-

Paragraph 0024, (2020/07/13)

The invention relates to the technical field of production of organic silicon by-products. The invention aims to solve the problems of high cost, more three wastes and continuous production of byproducts in the traditional organic silicon byproduct treatment process. The method comprises the following steps: adding the organic silicon by-product into a nitrogen-protected glass lining reaction kettle with a tower, adding a catalyst, dropwise adding alcohol to the bottom of the glass lining reaction kettle, carrying out a heating reaction under a stirring condition, neutralizing the obtained material, and rectifying the neutralized material to obtain the organic silane. According to the method, the multi-component organic silicon by-products trichlorosilane and silicon tetrachloride react and are converted into the same product, the high-purity product can be obtained only through simple rectification and purification, the process is simple, the treatment cost is low, and the product hasgood economic value.

Direct transformation of silica from natural resources to form tetramethoxysilane

Putro, Wahyu S.,Fukaya, Keisuke,Choi, Jun-Chul,Choi, Seong Jib,Horikoshi, Toshio,Sato, Kazuhiko,Fukaya, Norihisa

, p. 958 - 962 (2020/09/04)

A simple and practical method for direct synthesis of tetramethoxysilane (TMOS) from silica (SiO2) and methanol was achieved using a base catalyst and acetal as a dehydrant under carbon dioxide (CO2). The production of TMOS was strongly influenced by the kind of the acetal used, with 2,2-dimeth-oxypropane identified as the most effective dehydrant. We observed that the acetal used enabled the production of a high yield of dimethyl carbonate (DMC), which promoted the TMOS production. DMC is an intermediate product from the reaction of CO2 and methanol, which supported the SiO2 depolymerization process. When the reaction is conducted with 2,2-dimethoxypropane at 260 °C for 24 h, TMOS can be produced in up to 59percent yield. For practical applications, the TMOS synthesis has been developed on a 250 mL and 1 L-scale reaction with constant yield (>50percent) from various silica resources.

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