1825-61-2

Usage

Uses

Used in Lab Ware:
Methoxytrimethylsilane is used as a quench agent for lab ware while handling hydrofluoric acid (HF) and pyridine.
Used in Organic Synthesis:
Methoxytrimethylsilane plays an important role in the synthesis of organic compounds and is used in the preparation of alfa-lithioalkoxysilanes by treating with tert-butyllithium.
Used in Water Repellent Applications:
Methoxytrimethylsilane is used as a water-repellent agent, providing a hydrophobic surface coating that repels water.
Used in Superhydrophobic Materials:
Superhydrophobic recycled polyethylene terephthalate (rPET) aerogels can be fabricated using rPET fibers and polyvinyl alcohol (PVA) and can be coated with MTMS. This coating provides a high water contact angle and low surface energy, making the material superhydrophobic.
Used in Weathering Resistance:
Methoxytrimethylsilane on diglycidyl bisphenol A resin (epoxy resin) shows weathering resistance on exposure to ultraviolet (UV) light by lowering the effect of color change by 45%. This makes it useful in applications where resistance to UV-induced degradation is important.

InChI:InChI=1/C4H12OSi/c1-4(2,3)5-6/h1-3,6H3

Synthetic route

4-(trimethylsilyl)morpholine (13368-42-8) + bromobutyric acid (2623-87-2) → Methoxytrimethylsilane (1825-61-2) + morpholinium hydrobromide (6377-82-8) + trimethylsilyl 4-morpholinobutyrate

Conditions	Yield
With methanol at 20℃; for 24h;	A n/a B 99.1% C 71%

methanol (67-56-1) + 1,2-Diphenyl-1,2-bis<1-(trimethylsiloxy)ethenyl>diphosphan (82340-08-7, 82340-09-8) → Methoxytrimethylsilane (1825-61-2) + acetic acid methyl ester (79-20-9) + 1,2-diphenyldiphosphane (34478-62-1)

Conditions	Yield
for 1h; Product distribution; Ambient temperature;	A n/a B n/a C 99%

1-cyclopropyl-1-methoxytetramethyldisilane (80631-66-9) → Methoxytrimethylsilane (1825-61-2) + 1,3-dimethyl-1,3-divinyl-1,3-disilacyclobutane (22053-38-9)

Conditions	Yield
at 680℃; under 4E-05 Torr;	A 99% B 42%

methanol (67-56-1) + 2,5-dimethyl-4-acetyl-5-trimethylsiloxy-1,3,4-oxadiazoline-2 (91482-61-0) → Methoxytrimethylsilane (1825-61-2) + trisacetylhydrazine (91482-60-9)

Conditions	Yield
In dichloromethane at 24℃; for 0.5h; Product distribution;	A n/a B 98%

(bromomethyl)trimethylsilane (18243-41-9) + sodium methylate (124-41-4) → Methoxytrimethylsilane (1825-61-2) + (methoxymethyl)trimethylsilane (14704-14-4)

Conditions	Yield
In methanol for 19h; Heating;	A 0.5% B 98%

Hexamethyldisiloxane (107-46-0) + carbonic acid dimethyl ester (616-38-6) → Methoxytrimethylsilane (1825-61-2)

Conditions	Yield
With methanol; aluminum oxide; potassium fluoride at 400℃;	98%

bis(trimethylsilyl)mercury (4656-04-6) + tributyltin methoxide (1067-52-3) → Methoxytrimethylsilane (1825-61-2) + bis(tri-n-butyltin) (813-19-4) + mercury

Conditions	Yield
In benzene 25°C; 0.1 h;	A 95% B 98% C 96%

methanol (67-56-1) + (2-Trimethylsilanyl-1-trimethylsilanyloxy-cyclopropyl)-phosphonic acid diethyl ester (80395-65-9) → Methoxytrimethylsilane (1825-61-2) + diethyl <1-hydroxy-2-(trimethylsilyl)cyclopropyl>phosphonate (80406-85-5)

Conditions	Yield
for 120h; Ambient temperature;	A 97% B 85%

(2-Trimethylsilanyl-1-trimethylsilanyloxy-cyclopropyl)-phosphonic acid diethyl ester (80395-65-9) → Methoxytrimethylsilane (1825-61-2) + diethyl <1-hydroxy-2-(trimethylsilyl)cyclopropyl>phosphonate (80406-85-5)

Conditions	Yield
With methanol for 120h; Ambient temperature;	A 97% B 85%

trimethylsilyl cyanide (7677-24-9) + potassium (pentafluoroethyl)trimethoxyborate → Methoxytrimethylsilane (1825-61-2) + potassium cyano-dimethoxypentafluoroethylborate

Conditions	Yield
In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;	A n/a B 97%

(bromomethyl)trimethylsilane (18243-41-9) + sodium methylate (124-41-4) → Methoxytrimethylsilane (1825-61-2) + (methoxymethyl)trimethylsilane (14704-14-4) + ethyl(methoxy)dimethylsilane (52686-75-6)

Conditions	Yield
In 1,4-dioxane; methanol for 21h; Product distribution; Mechanism; Heating; variation of solvents and reaction time;	A 1.2% B 96% C 0.3%
In 1,4-dioxane for 7h; Heating;	A 6% B 1% C 80%
In 1,4-dioxane; methanol for 18h; Heating;	A 9% B 24% C 60%

trimethylsilyl cyanide (7677-24-9) + tetraphenylphosphonium bromide (2751-90-8) + potassium trimethoxy(trifluoromethyl)boranuide → Methoxytrimethylsilane (1825-61-2) + tetraphenylphosphonium dicyanomethoxytrifluoromethylborate

Conditions	Yield
Stage #1: trimethylsilyl cyanide; potassium trimethoxy(trifluoromethyl)boranuide at 70℃; for 2.5h; Stage #2: tetraphenylphosphonium bromide In water	A n/a B 96%

methanol (67-56-1) + 3-(trimethylsilyl)-2-oxazolidinone (43112-38-5) → Methoxytrimethylsilane (1825-61-2)

Conditions	Yield
chloro-trimethyl-silane at 0℃; for 0.0166667h;	95%

sodium methylate (124-41-4) + bis(trimethylsilyl) [2-(2-furyl)-1-(trimethylsilyloxycarbonyl)ethyl]phosphonite (333361-87-8) → Methoxytrimethylsilane (1825-61-2) + sodium [2-(2-furyl)-1-(sodiooxycarbonyl)ethyl]phosphonite

Conditions	Yield
In methanol Heating;	A n/a B 95%

sodium methylate (124-41-4) + bis(trimethylsilyl) 2-(2-furyl)ethylphosphonite (333364-16-2) → Methoxytrimethylsilane (1825-61-2) + sodium 2-(2-furyl)ethylphosphonite

Conditions	Yield
In methanol Heating;	A n/a B 94%

sodium methylate (124-41-4) + bis(trimethylsilyl) 2,4-bis(2-furyl)butylphosphonite (333364-17-3) → Methoxytrimethylsilane (1825-61-2) + sodium 2,4-bis(2-furyl)butylphosphonite

Conditions	Yield
In methanol Heating;	A n/a B 93%

methanol (67-56-1) + N-Trimethylsilyl-trifluormethansulfonimidoyl-Ethylester → ethyl methyl ether (540-67-0) + Methoxytrimethylsilane (1825-61-2) + Trifluoromethanesulfonamide (421-85-2)

Conditions	Yield
Heating;	A n/a B n/a C 92%

trimethylsilyl cyanide (7677-24-9) + (E)-methyl cinnamyl carbonate (87802-71-9, 85217-69-2) → Methoxytrimethylsilane (1825-61-2) + (E)-4-phenyl-3-butenenitrile (20068-10-4)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 16h; Heating;	A n/a B 92%

trimethylsilyl cyanide (7677-24-9) + methyl mirtenyl carbonate → Methoxytrimethylsilane (1825-61-2) + (6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-acetonitrile

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 15h; Heating;	A n/a B 92%

C--N-(trimethylsilyl)nitrilimine (116889-36-2) → Methoxytrimethylsilane (1825-61-2) + (diazo)methane (113597-81-2)

Conditions	Yield
With methanol Yields of byproduct given;	A n/a B 92%

trimethylsilyl cyanide (7677-24-9) + sodium tetramethoxyborate (18024-69-6) → Methoxytrimethylsilane (1825-61-2) + C4H3BN3O(1-)*Na(1+)

Conditions	Yield
at 60℃; for 48h;	A n/a B 92%

trimethylsilyl cyanide (7677-24-9) + potassium (pentafluoroethyl)trimethoxyborate → Methoxytrimethylsilane (1825-61-2) + potassium dicyanomethoxypentafluoroethylborate

Conditions	Yield
Stage #1: trimethylsilyl cyanide; potassium (pentafluoroethyl)trimethoxyborate at 20℃; for 20h; Inert atmosphere; Stage #2: With dihydrogen peroxide; potassium carbonate In water at 20℃; for 2h;	A n/a B 92%

methanol (67-56-1) + trimethyl(phenanthren-9-ylmethyl)silane (114099-91-1) → Methoxytrimethylsilane (1825-61-2) + 9-(methoxymethyl)phenanthrene (57741-37-4)

Conditions	Yield
With copper(II) bis(tetrafluoroborate) In acetonitrile for 40h; Irradiation;	A n/a B 91%

methanol (67-56-1) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → Methoxytrimethylsilane (1825-61-2)

Conditions	Yield
Stage #1: 1,1,1,3,3,3-hexamethyl-disilazane With C12H24KO6(1+)*Br3H(1-) In acetonitrile at 20℃; for 0.0166667h; Stage #2: methanol In acetonitrile at 20℃; for 0.333333h;	90%

cis-Re(CO)4(PPh3)CH2OCH3 + trimethylsilyl iodide (16029-98-4) → cis-Re(CO)4(PPh3)(iodomethyl) + Methoxytrimethylsilane (1825-61-2)

Conditions	Yield
In dichloromethane under N2, addn. at -78°C, allowed to warm to room temp.; removal of solvent in vac., dissolved in CH2Cl2/hexane, cooled to -5°C, filtered; elem. anal.;	A 90% B n/a

1,1-dimethoxy-1-phenyl-2,2,2-trimethyldisilane (40633-36-1) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → Methoxytrimethylsilane (1825-61-2) + 1-methoxy-1-phenyl-3,4-dimethyl-1-silacyclopent-3-ene (145431-92-1)

Conditions	Yield
at 500℃; under 0.001 Torr;	A n/a B 89%

2-Diethylamino-4-phenyl-3-trimethylsilyl-1,3-butadien-1,1-dicarbonsaeuredimethylester → Methoxytrimethylsilane (1825-61-2) + (Z)-3-Benzyliden-2-diethylamino-4-oxo-1-cyclobuten-1-carbonsaeuremethylester

Conditions	Yield
at 200℃; under 0.1 Torr;	A n/a B 89%

methanol (67-56-1) + chloro-trimethyl-silane (75-77-4) → Methoxytrimethylsilane (1825-61-2)

Conditions	Yield
With urea at 20℃; for 4h;	88.1%
With triethylamine at 20℃; for 0.05h; Inert atmosphere;	85%
With aniline 1.) 20 deg C, 15 min, 2.) boiling water bath, 20 min;	23%

methanol (67-56-1) + 1-<(trimethylsilyl)methyl>naphthalene (18410-58-7) → Methoxytrimethylsilane (1825-61-2) + 1-(methoxymethyl)naphthalene (5903-23-1)

Conditions	Yield
With copper(II) bis(tetrafluoroborate) In acetonitrile for 43h; Irradiation;	A n/a B 88%

trimethylsilyl cyanide (7677-24-9) + cyclohex-2-enyl methyl carbonate (58329-99-0) → Methoxytrimethylsilane (1825-61-2) + cyclohex-2-enecarbonitrile (13048-17-4)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 18h; Heating;	A n/a B 88%

Methoxytrimethylsilane (1825-61-2) + 1-O-trimethylsilyl-2,3,5-tri-O-benzyl-D-ribofuranose → methyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside (64363-77-5, 79083-29-7, 79083-32-2, 79083-33-3, 79083-40-2, 79083-41-3, 79083-43-5, 79083-44-6, 85549-73-1, 85610-74-8, 89824-86-2, 131615-65-1, 131896-99-6, 135910-14-4, 135911-60-3, 55725-85-4) + (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran (79083-29-7)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; diphenyltin sulfide In dichloromethane for 2h; Ambient temperature;	A 99% B 1%
With trimethylsilyl trifluoromethanesulfonate; lithium perchlorate; diphenyltin sulfide In dichloromethane for 2h; Ambient temperature;	A 5% B 95%

Methoxytrimethylsilane (1825-61-2) + 2,3-Dimethoxy-4-[(triisopropylsilanyl)-ethynyl]-4-trimethylsilanyloxy-cyclobut-2-enone (210486-69-4) → 3,4,4-Trimethoxy-2-[(triisopropylsilanyl)-ethynyl]-cyclobut-2-enone (210486-72-9)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran at 25℃; for 0.5h;	99%

Methoxytrimethylsilane (1825-61-2) + trans-1,2-cyclohexandiol (1460-57-7) + benzil (134-81-6) → (2R,3R,4aS,8aS)-2,3-Dimethoxy-2,3-diphenyl-octahydro-benzo[1,4]dioxine

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 3h;	99%

Methoxytrimethylsilane (1825-61-2) + C15H17O2Pol + C18H27NO5 (1148107-24-7) → C35H48NO7Pol

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate at 0 - 20℃; solid phase reaction;	99%

Methoxytrimethylsilane (1825-61-2) + C15H17O2Pol + C20H45NO5Si3 (1148107-25-8) → C28H42NO7Pol

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate at 0 - 20℃; solid phase reaction;	99%

diethyl (2S,3S)-tartrate (13811-71-7) + Methoxytrimethylsilane (1825-61-2) + C15H17O2Pol → C25H35O8Pol

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate at 0 - 20℃; solid phase reaction;	99%

Methoxytrimethylsilane (1825-61-2) + C15H17O2Pol + trans-1,2-cyclohexandiol (1460-57-7) → C23H33O4Pol

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate at 0 - 20℃; solid phase reaction;	99%

Methoxytrimethylsilane (1825-61-2) + trimethylsilyl cyanide (7677-24-9) → trimethylsilyl fluoride (420-56-4) + C4H3BN3O(1-)*Li(1+)

Conditions	Yield
With lithium tetrafluoroborate at 20℃; for 48h; Product distribution / selectivity;	A n/a B 99%

Methoxytrimethylsilane (1825-61-2) + trimethylsilyl cyanide (7677-24-9) + ortho-bromobenzaldehyde (6630-33-7) → 2-(2-bromophenyl)-2-methoxyacetonitrile (1415388-63-4)

Conditions	Yield
Stage #1: Trimethylmethoxysilane; ortho-bromobenzaldehyde With iron(III) chloride at 0℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: trimethylsilyl cyanide at 0℃; for 1.33333h; Inert atmosphere; Schlenk technique;	99%
Stage #1: Trimethylmethoxysilane; ortho-bromobenzaldehyde With iron(III) chloride In neat (no solvent) at 0℃; for 2h; Inert atmosphere; Stage #2: trimethylsilyl cyanide In neat (no solvent) at 0℃; for 1.33333h; Inert atmosphere;	88%

2,3,5-tri-O-benzyl-D-ribofuranose (16838-89-4) + Methoxytrimethylsilane (1825-61-2) → methyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside (64363-77-5, 79083-29-7, 79083-32-2, 79083-33-3, 79083-40-2, 79083-41-3, 79083-43-5, 79083-44-6, 85549-73-1, 85610-74-8, 89824-86-2, 131615-65-1, 131896-99-6, 135910-14-4, 135911-60-3, 55725-85-4)

Conditions	Yield
With trifluoromethylsulfonic anhydride; diphenyltin sulfide; cesium fluoride In diethyl ether	98%

Methoxytrimethylsilane (1825-61-2) + 2''-(tert-Butyl-diphenyl-silanyloxymethyl)-[2,4';2',4'']teroxazole-4-carbaldehyde (194232-63-8) → 2''-(tert-Butyl-diphenyl-silanyloxymethyl)-4-dimethoxymethyl-[2,4';2',4'']teroxazole (213738-68-2)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -40℃;	98%

1,1'-bis(dibromoboryl)ferrocene + Methoxytrimethylsilane (1825-61-2) → [Fe(C5H4B(OCH3)Br)2] (934672-99-8)

Conditions	Yield
In pentane (N2); Schlenk technique; soln. of MeOSiMe3 in pentane was added to suspn. of Fe complex in pentane at -78°C; mixt. was slowly warmed to room temp.; stirred overnight; volatiles removed (vac.); recrystd. (hexane);	98%

Methoxytrimethylsilane (1825-61-2) + vanadium(V) oxychloride (7727-18-6) → VOCl(methoxide)2 (62449-99-4)

Conditions	Yield
In dichloromethane byproducts: (CH3)3SiCl; (N2); addn. of 5 equiv. of silane deriv. to CH2Cl2 soln. of vanadium compd. at room temp., stirring for 16 h at room temp.; evapn., elem. anal.;	98%

Methoxytrimethylsilane (1825-61-2) + 2,3,8-trioxocephalotaxane (114956-74-0) → 2-methoxy-3,8-dioxocephalotax-1-ene (114942-83-5)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane for 24h;	97%

2,3-Pentanedione (600-14-6) + Methoxytrimethylsilane (1825-61-2) + trans-1,2-cyclohexandiol (1460-57-7) → (2R,3R,4aS,8aS)-2-Ethyl-2,3-dimethoxy-3-methyl-octahydro-benzo[1,4]dioxine

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 3h;	97%

Methoxytrimethylsilane (1825-61-2) + trans-1,2-cyclohexandiol (1460-57-7) + dimethylglyoxal (431-03-8) → (2R,3R,4aS,8aS)-2,3-Dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 3h;	97%

Methoxytrimethylsilane (1825-61-2) + niobium pentachloride (10026-12-7) → trichlorodimethoxyniobium(V) (91846-25-2)

Conditions	Yield
In dichloromethane byproducts: trimethylchlorosilane; reaction at -78°C, then was allowed to warm to room temp., concentreting under reduced pressure, hexane was added to give a white crist. solid (all in an inert atmosphere); washing with hexane, dried under vac., elem.anal.;	97%

Methoxytrimethylsilane (1825-61-2) + (±)-demethylcephalotaxinone (38848-25-8) → (±)-cephalotaxinone (38750-57-1, 38848-26-9)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 0 - 40℃; Inert atmosphere;	97%

Methoxytrimethylsilane (1825-61-2) + 1-Trimethylsilanylmethyl-cyclododecanecarbaldehyde (118813-73-3) → 1-Methoxy-2-methylene-cyclotridecane (113541-76-7)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane Ambient temperature;	96%

Upstream product

• 110-86-1 pyridine 
• 67-56-1 methanol 
• 75-77-4 chloro-trimethyl-silane 
• 108-88-3 toluene 
• 107-46-0 Hexamethyldisiloxane 
• 141-62-8 decamethyltetrasiloxane 
• 3768-55-6 N-trimethylsilylaniline 
• 681-84-5 tetramethylorthosilicate 
• 676-58-4 methylmagnesium chloride 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 762-72-1 allyl-trimethyl-silane 
• 2295-12-7 1,1-dimethylsilacyclobutane 
• 2370-88-9 2,4,6,8-tetramethylcyclotetrasiloxane 
• 13368-42-8 4-(trimethylsilyl)morpholine 

Downstream Products

• 10497-05-9 Tris(trimethylsilyl) phosphate 
• 56859-42-8 C₇H₈F₃OP 
• 650-99-7 Phenylphosphonsaeure-methylester-fluorid 
• 79186-48-4 fluoro-1, methoxy-2, phenyl-2 ethane 
• 124646-81-7 1-(3-methoxy-5-methyloct-5-enyl)benzene 
• 51849-23-1 Methyl trimethylsilyl malonate 
• 1000-49-3 n-butyltrimethylsilane 
• 53963-25-0 [1-((Z)-2-Methoxy-vinyl)-butylsulfanyl]-benzene 
• 53963-24-9 [1-((E)-2-Methoxy-vinyl)-butylsulfanyl]-benzene 
• 1825-63-4 trimethyl(propoxy)silane 
• 19108-51-1 trimethyl-trideuteriomethoxy-silane 
• 67-56-1 methanol 
• 1825-62-3 ethyl trimethylsilyl ether 
• 353-88-8 O-methyl methanephosphonofluoridate 

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3-Oxo 2-propenoic acid methyl ester has been prepared by flash vacuum pyrolysis and characterized by mass spectrometry and chemical trapping.Its four-membered cyclic dimers have been isolated.

The use of phosphorus pentafluoride as a fluorinating agent in organosilicon chemistry. III. Synthesis and characterization of some new fluorosiloxanes

Although the silicon-oxygen bond of siloxanes and alkoxysilanes is readily cleaved by phosphorus pentafluoride, the silicon-hydrogen bond of hydrosiloxanes can be easily fluorinated at low temperatures by this reagent thus providing a convenient source of fluorosiloxanes. The synthesis and characterization of FSiH2OSiH3, (FSiH2)2O, F(CH3)HSiOSiH2CH3, and [F(CH3)HSi]2O are described.

Contributions to the chemistry of halosilane adducts XVIII. On the nature of compounds of trimethylhalosilanes with 1,1,3,3-tetramethylguanidine and 2-trimethylsilyl-1,1,3,3-tetramethylguanidine: preparation and characterization of mono- and bis-(2-trimet

1,1,3,3-Tetramethylguanidine (TMG) and 2-(trimethylsilyl)-1,1,3,3-tetramethyl-guanidine (TMSTMG) react with trimethylhalosilanes Me3SiHal in equimolar ratio with ionization of the Si-halogen bond to give the stable guanidinium salts Hal (