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chloro-trimethyl-silane
dichloromethane
A
bis(trimethylsilyl)methane
B
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
With N,N,N,N-tetraethylammonium tetrafluoroborate In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 18.4167h; electroreduction, anode: Al, cathode: stainless steel; | A 10% B 90% |
Conditions | Yield |
---|---|
With methylmagnesium bromide In not given | 90% |
With CH3MgBr In not given | 90% |
chloro-trimethyl-silane
dichloromethane
A
bis(trimethylsilyl)methane
B
1,2-bis(trimethylsilyl)ethane
C
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
With N,N,N,N-tetraethylammonium tetrafluoroborate In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 33.5h; electroreduction, anode: Al, cathode: stainless steel; | A 88% B 6% C 6% |
Conditions | Yield |
---|---|
In neat (no solvent, gas phase) vapor phase chlorination at temp. of boiling benzene;; | 74% |
In tetrachloromethane Irradiation (UV/VIS); introduction of gaseous Cl2 into a soln. of Si(CH3)4 in CCl4 under irradiation with sunlight in presence of some PCl5;; | 33% |
Chloro(chloromethyl)dimethylsilane
methylmagnesium bromide
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
42% | |
With diethyl ether |
tetramethylsilane
Chloro(chloromethyl)dimethylsilane
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
aluminium trichloride In tetrachloromethane for 6h; Heating; atmospheric pressure; | 33% |
tetramethylsilane
Chloro(chloromethyl)dimethylsilane
A
chloro-trimethyl-silane
B
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
aluminium trichloride In neat (no solvent) at 30 - 40℃; for 19h; Product distribution; atmospheric pressure; other time and solvents, different ratio of the starting materials; | A n/a B 32% |
tetramethylsilane
A
methanesulfonyl trimethylsilyl chloride
B
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
With yttrium(III) chloride; sulfuryl dichloride for 8h; Irradiation; | A 20% B 20% |
methyl magnesium iodide
(chloromethyl)trichlorosilane
A
iodo(trimethylsilyl)methane
B
Chloromethyltrimethylsilane
diethyl ether
Chloro(chloromethyl)dimethylsilane
methylmagnesium chloride
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
With tetrachloromethane; phosphorus pentachloride; chlorine unter Belichtung; | |
With tetrachloromethane; potassium carbonate; acetonitrile; bis(triphenylphosphine)platinum(II) dichloride at 120℃; for 16h; | 2.4 % Chromat. |
n-Butyl chloride
(bromomethyl)trimethylsilane
A
1-bromo-butane
B
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
With triisooctyl amine Equilibrium constant; |
n-Butyl chloride
iodo(trimethylsilyl)methane
A
1-iodo-butane
B
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
With triisooctyl amine Equilibrium constant; |
trichloromethyltrimethylsilane
Dilithium N,N'-bis(trimethylsilyl)hydrazide tetramer
A
chloro-trimethyl-silane
B
(dichloromethyl)trimethylsilane
C
N,N'-bis(trimethylsilyl)hydrazine
D
tris(trimethylsilyl)hydrazine
E
1,1,1,3,3,3-hexamethyl-disilazane
F
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
In diethyl ether at -78℃; Product distribution; var.: reagent; |
tetrachloromethane
tetramethylsilane
phosphorus pentachloride
chlorine
Chloromethyltrimethylsilane
bis(chloromethyl)dimethylsilane
A
tetramethylsilane
B
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
With Zn In ethanol; water react. of (CH3)2Si(CH2Cl)2 and Zn powder in aq. ethanol in presence of NaI and Na2CO3;; |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78℃; |
(dichloromethyl)trimethylsilane
A
chloro-trimethyl-silane
B
tetramethylsilane
C
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
With hydrogen at 200℃; under 760.051 Torr; for 1h; Kinetics; Flow reactor; | |
With hydrogen at 200℃; under 760.051 Torr; for 1h; Kinetics; Flow reactor; |
(dichloromethyl)trimethylsilane
A
chloro-trimethyl-silane
B
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
With hydrogen at 200℃; under 760.051 Torr; for 1h; Kinetics; Flow reactor; |
benzylamine
Chloromethyltrimethylsilane
N-benzyl-1-(trimethylsilyl)-N-((trimethylsilyl)methyl)methanamine
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile Heating; | 100% |
With potassium carbonate In acetonitrile for 68h; Heating; | 76% |
trimethylsilylmethyllithium
Chloromethyltrimethylsilane
lithium hydride
Conditions | Yield |
---|---|
In tetrahydrofuran; water; pentane | 100% |
3-fluorosalicylaldehyde
Chloromethyltrimethylsilane
3-fluoro-2-((trimethylsilyl)methoxy)benzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 65℃; for 12h; Inert atmosphere; | 100% |
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 65℃; | 98% |
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 65℃; |
furfural
Chloromethyltrimethylsilane
1-(2'-furyl)-2-trimethylsilanylethan-1-ol
Conditions | Yield |
---|---|
Stage #1: Chloromethyltrimethylsilane With magnesium In diethyl ether at 20℃; for 1h; Stage #2: furfural In diethyl ether at 0 - 20℃; for 1h; | 99% |
With magnesium In diethyl ether at 0 - 20℃; for 12h; Grignard reaction; | 90% |
Stage #1: Chloromethyltrimethylsilane With magnesium In diethyl ether for 1h; Grignard reaction; Heating; Stage #2: furfural In diethyl ether at 0 - 20℃; for 12h; Addition; Further stages.; | 90% |
Stage #1: Chloromethyltrimethylsilane With magnesium In diethyl ether for 1h; Heating; Stage #2: furfural In diethyl ether for 12h; Grignard reaction; Further stages.; | 90% |
Stage #1: Chloromethyltrimethylsilane With 1,1-Dibromoethane; magnesium In diethyl ether for 18h; Heating; Stage #2: furfural In diethyl ether at 0 - 23℃; for 18h; Grignard reaction; |
2-Mercaptopyridine
Chloromethyltrimethylsilane
2-(trimethylsilylmethylmercapto)pyridine
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In ethanol for 1h; Heating; | 98% |
Conditions | Yield |
---|---|
Stage #1: Chloromethyltrimethylsilane With magnesium In diethyl ether at 20℃; for 1h; Stage #2: thiophene-2-carbaldehyde In diethyl ether at 0 - 20℃; for 1h; | 98% |
Stage #1: Chloromethyltrimethylsilane With magnesium; ethylene dibromide In diethyl ether for 1h; Heating; Stage #2: thiophene-2-carbaldehyde In diethyl ether at 0 - 20℃; for 21h; | 94% |
2-bromo-4,5-dichloro-1 H-imidazole
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In N,N-dimethyl acetamide at 0 - 100℃; for 4h; | 98% |
Chloromethyltrimethylsilane
trimethylsilylmethyl azide
Conditions | Yield |
---|---|
With sodium azide In N,N-dimethyl-formamide at 80℃; for 44h; | 97% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide at 80℃; for 12h; | 95% |
With sodium azide In N,N-dimethyl-formamide at 80℃; for 40h; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
In neat (no solvent) at 70℃; for 2h; Inert atmosphere; | 97% |
In N,N-dimethyl-formamide at 100℃; for 20h; | 95% |
(+)-(S)-1-Phenyl-3,4,5,6-tetrahydro[1,2]thiazin-1-oxide
Chloromethyltrimethylsilane
(+)-(1S,6S)-6-(trimethylsilyl)methyl-1-phenyl-3,4,5,6-tetrahydro-1λ4-1,2-thiazine 1-oxide
Conditions | Yield |
---|---|
Stage #1: (+)-(S)-1-Phenyl-3,4,5,6-tetrahydro[1,2]thiazin-1-oxide With n-butyllithium In tetrahydrofuran; hexane at -50 - 20℃; Stage #2: Chloromethyltrimethylsilane In tetrahydrofuran; hexane at -78 - 20℃; for 18h; optical yield given as %de; diastereoselective reaction; | 97% |
Chloro(chloromethyl)dimethylsilane
Chloromethyltrimethylsilane
chloromethyl(dimethyl)(trimethylsilylmethyl)silane
Conditions | Yield |
---|---|
Stage #1: Chloromethyltrimethylsilane With magnesium; ethylene dibromide In tetrahydrofuran for 2h; Schlenk technique; Inert atmosphere; Reflux; Stage #2: Chloro(chloromethyl)dimethylsilane In tetrahydrofuran for 20h; Reflux; Schlenk technique; Inert atmosphere; | 97% |
tert-butylamine
Chloromethyltrimethylsilane
N-tert-butyl<(trimethylsilyl)metyl>amine
Conditions | Yield |
---|---|
Stage #1: tert-butylamine; Chloromethyltrimethylsilane at 200℃; for 18h; Stage #2: With sodium hydroxide In water | 96% |
at 200℃; for 18h; Product distribution / selectivity; Heating / reflux; | 96% |
Stage #1: tert-butylamine; Chloromethyltrimethylsilane at 200℃; for 18h; Stage #2: With sodium hydroxide In water at 20℃; for 1h; Product distribution / selectivity; | 96% |
methyltris(trimethylsilyl)silane
Chloromethyltrimethylsilane
2-[(trimethylsilyl)methyl]heptamethyltrisilane
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran Inert atmosphere; | 96% |
Chloromethyltrimethylsilane
1,4-bis(trimethylsilyl)dodecamethylbicyclo[2.2.2]octasilane
1-(trimethylsilyl)-4-[(trimethylsilyl)methyl]dodecamethylbicyclo[2.2.2]octasilane
Conditions | Yield |
---|---|
Stage #1: 1,4-bis(trimethylsilyl)dodecamethylbicyclo[2.2.2]octasilane With potassium tert-butylate In tetrahydrofuran Inert atmosphere; Stage #2: Chloromethyltrimethylsilane In tetrahydrofuran at 20℃; for 16.1667h; Cooling with ice; Inert atmosphere; | 96% |
thiophenol
Chloromethyltrimethylsilane
(phenylsulfanylmethyl)trimethylsilane
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 4h; Heating; | 95% |
benzylamine
Chloromethyltrimethylsilane
N-(trimethylsilylmethyl)benzylamine
Conditions | Yield |
---|---|
In dimethyl sulfoxide Heating; | 95% |
at 20 - 120℃; for 24h; | 93.3% |
In acetonitrile for 16h; Reflux; Inert atmosphere; | 93% |
p-Chlorothiophenol
Chloromethyltrimethylsilane
<(4-chlorophenylthio)methyl>trimethylsilane
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 4h; Heating; | 95% |
Chloromethyltrimethylsilane
1,1,1-trichloro-3,3-dimethyl-1,3-disilabutane
Conditions | Yield |
---|---|
With trichlorosilane; tetra-n-butylphosphonium chloride at 150℃; for 4h; | 95% |
With trichlorosilane; benzyltriphenylphosphonium chloride | 72% |
With trichlorosilane; benzyltriphenylphosphonium chloride | 72% |
With tetrachlorosilane; magnesium; methyl iodide 1.) THF, reflux, 0.5 h, 2.) THF, 80 deg C, 4 h; Yield given. Multistep reaction; |
2-mercaptobenzimidazole sodium salt
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
In benzene for 4h; Heating; | 95% |
(R)-1-phenyl-ethyl-amine
Chloromethyltrimethylsilane
(R)-(+)-N-1-phenylethyl-N-trimethylsilylmethylamine
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 90℃; for 18h; | 95% |
Heating; | 84% |
With potassium carbonate In acetonitrile for 4h; Heating; | 81% |
Conditions | Yield |
---|---|
Stage #1: Chloromethyltrimethylsilane With magnesium In diethyl ether Heating; Stage #2: furan-3-carboxaldehyde In diethyl ether at 0 - 20℃; for 12h; Further stages.; | 95% |
Stage #1: Chloromethyltrimethylsilane With 1,1-Dibromoethane; magnesium In diethyl ether for 19h; Heating; Stage #2: furan-3-carboxaldehyde In diethyl ether at 0 - 23℃; for 18h; Grignard reaction; |
1-methyl-4-((phenylsulfonyl)methyl)benzene
Chloromethyltrimethylsilane
Conditions | Yield |
---|---|
With lithium methylsulfinyl carbanion at 20℃; for 2h; Product distribution; Further Variations:; Reagents; Temperatures; | 95% |
Chloromethyltrimethylsilane
1-cyclopropyl-5,9-dimethyl-deca-4,8-dien-1-one
(E)-2-Cyclopropyl-6,10-dimethyl-1-trimethylsilanyl-undeca-5,9-dien-2-ol
Conditions | Yield |
---|---|
Stage #1: Chloromethyltrimethylsilane With magnesium In diethyl ether Stage #2: With cerium(III) chloride In tetrahydrofuran; diethyl ether at 0℃; Stage #3: 1-cyclopropyl-5,9-dimethyl-deca-4,8-dien-1-one In tetrahydrofuran; diethyl ether at 0 - 20℃; | 95% |
Conditions | Yield |
---|---|
In pentane | 95% |
In pentane | 95% |
In pentane at 40℃; for 16h; Argon gasification; | 80% |
ethyl cinnamate
Chloromethyltrimethylsilane
trimethyl[(3E)-2-methylene-4-phenylbut-3-en-1-yl]silane
Conditions | Yield |
---|---|
Stage #1: Chloromethyltrimethylsilane With magnesium In tetrahydrofuran at 20℃; for 3h; Stage #2: ethyl cinnamate With cerium(III) chloride In tetrahydrofuran at -78 - 20℃; Stage #3: With silica gel In dichloromethane at 20℃; for 3h; Further stages.; | 95% |
tributyltin chloride
magnesium
Chloromethyltrimethylsilane
(trimethylsilyl)(tributylstannyl)methane
Conditions | Yield |
---|---|
With iodine; ammonium chloride In diethyl ether N2-atmosphere; addn. of Me3SiCH2Cl to Mg (activated with I2), refluxing(1 h), addn. of Bu3SnCl, refluxing (18 h); addn. of satd. aq. NH4Cl, extn. of aq. layer (ether), washing of org. layer (satd. aq. NaCl), drying (Na2SO4), evapn. of ether, distn. (vac.); | 95% |
2-chloro-1-(2,4-dichlorophenyl)ethanone
(trimethylsilyl)methylmagnesium chloride
Chloromethyltrimethylsilane
1-(1-chloromethylethenyl)-2,4-difluorobenzene
Conditions | Yield |
---|---|
Stage #1: (trimethylsilyl)methylmagnesium chloride; Chloromethyltrimethylsilane With magnesium In tert-butyl methyl ether at 55℃; for 4h; Stage #2: 2-chloro-1-(2,4-dichlorophenyl)ethanone In tert-butyl methyl ether at -10 - 0℃; Stage #3: With sulfuric acid In tert-butyl methyl ether at 25 - 50℃; for 3h; | 95% |
(S)-1-phenyl-ethylamine
Chloromethyltrimethylsilane
N-(S)-α-methylbenzyl-N-((trimethylsilyl)methyl)amine
Conditions | Yield |
---|---|
In neat (no solvent) at 200℃; for 3h; Sealed tube; | 94% |
With triethylamine for 16h; Reflux; Inert atmosphere; | 76% |
With potassium carbonate In acetonitrile for 4h; Heating; | 75% |
(Z)-3-bromo-4-trimethylsilyl-3-buten-2-one
Chloromethyltrimethylsilane
(Z)-2-bromo-3-methyl-1-trimethylsilyl-1,3-butadiene
Conditions | Yield |
---|---|
Stage #1: Chloromethyltrimethylsilane With magnesium; ethylene dibromide In diethyl ether for 1h; Inert atmosphere; Reflux; Stage #2: (Z)-3-bromo-4-trimethylsilyl-3-buten-2-one In diethyl ether at 0℃; Peterson olefination; Inert atmosphere; Stage #3: With water; acetic acid at 50℃; for 6h; Peterson olefination; Inert atmosphere; | 94% |
Chloromethyltrimethylsilane
2-(trimethylsilyl)-2-[(trimethylsilyl)methyl]hexamethyltrisilane
Conditions | Yield |
---|---|
In benzene at 0℃; for 2h; | 94% |
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