1,1,2,2-tetrachloro-1,2-dimethyldisilane
A
Dichloromethylsilane
B
Methyltrichlorosilane
Conditions | Yield |
---|---|
silica gel; 3,5-Dimethyl-1-<(2-triethoxysilyl)ethyl>-1H-pyrazol Product distribution; Mechanism; Heating; var. of catalyst, also with HCl; | A 0.4% B 99.6% |
(chloromethyl)trichlorosilane
HSiPh3
A
Methyltrichlorosilane
B
Triphenylsilyl chloride
Conditions | Yield |
---|---|
at 165 - 250℃; for 12h; | A 87.3% B 95.8% |
at 165 - 210℃; for 12h; | A 95.8% B 87.3% |
(chloromethyl)trichlorosilane
methyldiphenylsilane
A
Methyltrichlorosilane
B
chloromethyldiphenylsilane
Conditions | Yield |
---|---|
at 125 - 210℃; for 12h; | A 90.2% B 95.6% |
at 125 - 210℃; for 12h; | A 95.6% B 90.2% |
(trichloromethyl)methyldichlorosilane
dimethylsilicon dichloride
A
Methyltrichlorosilane
B
(trichloromethyl)dimethylchlorosilane
Conditions | Yield |
---|---|
triphenylphosphine for 1h; Heating; | A n/a B 95% |
tetrachloromethane
1,1,2,2-tetrachloro-1,2-dimethyldisilane
A
Methyltrichlorosilane
B
(trichloromethyl)methyldichlorosilane
Conditions | Yield |
---|---|
dichlorotris(triphenylphosphine)ruthenium(II) for 3h; Heating; | A n/a B 94% |
triphenylphosphine for 2h; Heating; | A 62% B 62% |
With triphenylphosphine at 80℃; for 2h; | A n/a B 62% |
trichloro(dichloromethyl)silane
methyldiphenylsilane
A
Methyltrichlorosilane
B
(chloromethyl)trichlorosilane
C
chloromethyldiphenylsilane
Conditions | Yield |
---|---|
at 160 - 240℃; for 6h; | A 15.6% B 81.2% C 93.1% |
Dichloromethylsilane
3-chloroprop-1-ene
A
Methyltrichlorosilane
B
dichloromethylpropylsilane
C
dichloro(3-chloropropyl)methylsilane
Conditions | Yield |
---|---|
With hexachloroplatinic acid; tributyl-amine; acetic acid at 35 - 39℃; Autoclave; Inert atmosphere; Industrial scale; | A 64 kg B 70 kg C 92.8% |
at 65℃; for 12h; | A 21.4% B 16.6% C 62% |
platinum(IV) chloride In C12-olefin at 70 - 100℃; for 2h; Product distribution / selectivity; | |
bis(1,5-cyclooctadiene)diiridium(I) dichloride In chlorobenzene at 67.42 - 175.15℃; under 1500.15 - 1522.65 Torr; Product distribution / selectivity; Heating / reflux; | |
Stage #1: Dichloromethylsilane; 3-chloroprop-1-ene; platinum at -30 - 90℃; for 3h; Inert atmosphere; Stage #2: With triphenylphosphine In toluene at 20℃; Product distribution / selectivity; |
(chloromethyl)trichlorosilane
Dimethylphenylsilane
A
Methyltrichlorosilane
B
phenyldimethylsilyl chloride
Conditions | Yield |
---|---|
at 125 - 210℃; for 2h; | A 91.4% B 88.6% |
trimethylsilan
(chloromethyl)trichlorosilane
A
chloro-trimethyl-silane
B
Methyltrichlorosilane
Conditions | Yield |
---|---|
at 500℃; for 0.00833333h; | A 86.8% B 91.2% |
at 500℃; for 0.00833333h; | A 91.2% B 86.8% |
β-chlorovinyl(methyl)dichlorosilane
A
Methyltrichlorosilane
B
1,1-dichloroethane
C
chloroethylene
Conditions | Yield |
---|---|
With hydrogenchloride; iron(III) chloride at 25 - 31℃; for 4h; Product distribution; Further Variations:; Temperatures; reaction time, reagent concentration; Addition; elimination; | A n/a B n/a C n/a D 89% |
silicon
A
Methyltrichlorosilane
B
tetrachlorosilane
C
trichlorosilane
D
dimethylsilicon dichloride
Conditions | Yield |
---|---|
With methylene chloride; copper In neat (no solvent) mixt. of CH3Cl/N2 (2:5) and Si-Cu (9:1) at 300°C;; | A 4% B n/a C n/a D 86.5% |
With methylene chloride; copper In neat (no solvent) mixt. of CH3Cl/N2 (2:5) and Si-Cu (9:1) at 300°C;; | A 4% B n/a C n/a D 86.5% |
With methylene chloride; copper In neat (no solvent) CH3Cl and Si-Cu mixt. (8:2) at 350°C;; |
dimethylmonochlorosilane
(chloromethyl)trichlorosilane
A
Methyltrichlorosilane
B
dimethylsilicon dichloride
Conditions | Yield |
---|---|
at 500℃; for 0.00833333h; | A 79.1% B 85.6% |
methylene chloride
silicon
A
Dichloromethylsilane
B
Methyltrichlorosilane
C
dimethylsilicon dichloride
Conditions | Yield |
---|---|
tin; aluminum silicide; zinc(II) oxide; copper dichloride at 280 - 300℃; for 6h; Rochow reaction; | A 1.7% B n/a C 83.8% |
zinc(II) oxide; copper dichloride at 280 - 300℃; for 6h; Rochow reaction; | A 4.5% B n/a C 83.7% |
zinc(II) oxide; aluminium; copper dichloride at 280 - 300℃; for 6h; Rochow reaction; | A 2.8% B n/a C 82.1% |
With PdSi at 400℃; for 6h; |
Conditions | Yield |
---|---|
With palladium silicide at 400 - 500℃; for 7.5h; Product distribution / selectivity; Inert atmosphere; | 82.8% |
With aluminum oxide; trichlorosilane at 300℃; anschliessend Lieten ueber einen Kupfer-Silicium-Katalysator; | |
With Pd2Si at 400 - 500℃; for 7.5h; Inert atmosphere; | |
With amorphous silicon at 600 - 700℃; Inert atmosphere; Schlenk technique; | |
With hexachlorodisilane; tetrabutyl-ammonium chloride at -78 - 20℃; Inert atmosphere; Sealed tube; |
Conditions | Yield |
---|---|
With trichlorosilane at 500℃; for 0.00833333h; | 75.3% |
Conditions | Yield |
---|---|
With tetrachlorosilane; palladium silicide; hydrogen at 400 - 850℃; for 5h; Product distribution / selectivity; | A 74% B 24% |
With copper; silicon at 300 - 390℃; | |
With nitrogen; copper; silicon at 300 - 390℃; |
Conditions | Yield |
---|---|
With methylene chloride In neat (no solvent) Si and a mixt. of CH3Cl and HCl (3:1) at 350°C;; | A 72% B n/a |
Conditions | Yield |
---|---|
With methylene chloride; copper In neat (no solvent) Si-Cu and a mixt. of CH3Cl, H2 and Cl2 at 350°C;; | 70.1% |
With methylene chloride; iron(III) chloride In neat (no solvent) | |
With methylene chloride; copper In neat (no solvent) CH3Cl and unpurified Si;; | |
With methylene chloride; aluminium trichloride In neat (no solvent) | |
With methylene chloride; tin(IV) chloride In neat (no solvent) |
tetramethylsilane
germaniumtetrachloride
A
Methyltrichlorosilane
B
methyltrichlorogermane
C
dimethylsilicon dichloride
D
dichlorodimethylgermanium
Conditions | Yield |
---|---|
aluminium bromide In neat (no solvent) molar ratio Me4Si/GeCl4 = 0.3/1, at 200°C for 65 h, cooled; NMR, mass spectra, chromy.; | A 30% B 68% C 70% D 32% |
Conditions | Yield |
---|---|
With thionyl chloride; N,N-dimethyl-formamide at 55℃; under 760.051 Torr; for 2h; | 60% |
With thionyl chloride; N,N-dimethyl-formamide at 55℃; for 2h; Reflux; | 60 %Spectr. |
Conditions | Yield |
---|---|
With thionyl chloride; N,N-dimethyl-formamide at 55℃; under 760.051 Torr; for 7h; | 60% |
With thionyl chloride; N,N-dimethyl-formamide at 55℃; for 7h; Reflux; | 60 %Spectr. |
dimethylmonochlorosilane
dimethylsilicon dichloride
A
Dichloromethylsilane
B
chloro-trimethyl-silane
C
Methyltrichlorosilane
D
chloro-methyl-silane
Conditions | Yield |
---|---|
With aluminium trichloride at 140℃; for 15h; | A 0.092 mol B 59% C 0.01 mol D 0.055 mol |
triethenylsilane
(chloromethyl)trichlorosilane
A
Methyltrichlorosilane
B
chlorotrivinylsilane
Conditions | Yield |
---|---|
at 500℃; for 0.00833333h; | A 41.5% B n/a |
methylene chloride
A
Dichloromethylsilane
B
Methyltrichlorosilane
C
dimethylsilicon dichloride
Conditions | Yield |
---|---|
With silicon; zinc at 325℃; for 24h; Reagent/catalyst; Inert atmosphere; | A n/a B n/a C 41.1% |
With copper(II) oxide; silicon; zinc at 325℃; for 24h; Reagent/catalyst; Inert atmosphere; | A n/a B n/a C 17.5% |
With silicon; bronze; cesium chloride; copper(l) chloride at 200 - 360℃; for 8h; Product distribution / selectivity; |
chloroform
1,1,2,2-tetrachloro-1,2-dimethyldisilane
A
Methyltrichlorosilane
B
(dichloromethyl)methyldichlorosilane
Conditions | Yield |
---|---|
triphenylphosphine | A n/a B 35% |
With triphenylphosphine at 140℃; for 4h; | A 98 % Chromat. B 29% |
Dichloromethylsilane
A
Methyltrichlorosilane
B
dimethylmonochlorosilane
C
chloro-methyl-silane
Conditions | Yield |
---|---|
dihydrogen hexachloroplatinate at 150℃; for 4h; | A 25.1% B 3.5% C 2.9% |
dihydrogen hexachloroplatinate at 150℃; for 4h; | A 25.1% B 3.5% C 2.9% |
chloromethyl-methyl-diphenyl-silane
A
Methyltrichlorosilane
B
biphenyl
C
chloromethyldiphenylsilane
D
Phenyltrichlorosilane
E
1,2-dichloro-ethane
Conditions | Yield |
---|---|
iron(III) chloride at 70℃; for 0.5h; Product distribution; other conditions: other catalyst, other temperature; | A 8% B 10% C 17% D 14% E 22% |
1,1,1,2,2,2-hexamethyldisilane
pentamethylchlorodisilane
1,2-dichlorotetramethylsilane
1,1,2-trichloro-1,2,2-trimethyldisilane
1,1,2,2-tetrachloro-1,2-dimethyldisilane
1,1-dichlorotetramethyldisilane
A
Dichloromethylsilane
B
chloro-trimethyl-silane
C
Methyltrichlorosilane
D
dimethylmonochlorosilane
E
dimethylsilicon dichloride
Conditions | Yield |
---|---|
With hydrogenchloride at 430 - 750℃; for 72h; Conversion of starting material; | A 4 %Chromat. B 12 %Chromat. C 7 %Chromat. D 6 %Chromat. E 21% |
methyl pentachlorodisilane
A
Methyltrichlorosilane
B
1,1-Dichloro-1-methyl-disilane
C
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
With trimethylstannane; triphenylphosphine Ambient temperature; | A 20% B n/a C n/a |
Methyltrichlorosilane
bis-(diethylamino)methane
A
N,N-diethyl(methylene)ammonium chloride
B
(diethylamino)dichloromethylsilane
Conditions | Yield |
---|---|
In hexane for 5h; Ambient temperature; | A 100% B 59% |
Conditions | Yield |
---|---|
In dichloromethane | 100% |
Methyltrichlorosilane
2-[(trimethylsilyl)oxy]benzoic acid trimethylsilyl ester
A
chloro-trimethyl-silane
Conditions | Yield |
---|---|
at 20℃; for 24h; | A 100% B 95% |
Methyltrichlorosilane
Conditions | Yield |
---|---|
With water In toluene at 50 - 60℃; Polymerization; hydrolytic polycondensation; | 99.6% |
Methyltrichlorosilane
Methyltrimethoxysilan
chlorobenzene
dimethoxy(methyl)phenylsilane
Conditions | Yield |
---|---|
Stage #1: Methyltrimethoxysilan; chlorobenzene With magnesium In tetrahydrofuran for 1h; Reflux; Stage #2: Methyltrichlorosilane; Methyltrimethoxysilan; chlorobenzene In tetrahydrofuran for 6.5h; Concentration; Reflux; | 99.6% |
Methyltrichlorosilane
sodium tri-tert-butylsilanide
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; Substitution; supersilanidation; | 99% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 1.5h; | 99% |
Conditions | Yield |
---|---|
In ethanol for 3h; | 99% |
Conditions | Yield |
---|---|
With polyaniline at 50 - 55℃; for 5h; | 98.3% |
Conditions | Yield |
---|---|
With chlorine Irradiation; | 98% |
With chlorine at 65℃; for 6.5h; Irradiation; visible light; | 68% |
With chlorine im UV-Licht; |
Conditions | Yield |
---|---|
With triethylamine In benzene for 2h; Heating; | 98% |
Methyltrichlorosilane
Conditions | Yield |
---|---|
at 30 - 35℃; for 4.5h; | 98% |
Conditions | Yield |
---|---|
With pyridine In benzene heating of (CH3)3SiCl and HOC6H4I in benzene in presence of pyridine;; | 98% |
With pyridine In benzene heating of (CH3)3SiCl and HOC6H4I in benzene in presence of pyridine;; | 98% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Schlenk technique; | 98% |
Methyltrichlorosilane
Conditions | Yield |
---|---|
With quinoline In benzene at 80℃; for 5h; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
at 200℃; for 6h; Temperature; Molecular sieve; Large scale; | 98% |
With bismuth(III) chloride at 25℃; for 24h; Inert atmosphere; | 85% |
With bismuth(III) chloride at 20℃; for 24h; Schlenk technique; Inert atmosphere; | 50 mol |
Methyltrichlorosilane
trichloromethyltrichlorosilane
Conditions | Yield |
---|---|
With chlorine In tetrachloromethane Irradiation; | 97% |
With Cl2 In chloroform CH3SiCl3 and Cl2 in CHCl3 below 25°C;; sublimation under reduced pressure;; | 95% |
With chlorine In chloroform CH3SiCl3 and Cl2 in CHCl3 above 70°C;; | 55% |
Conditions | Yield |
---|---|
With pyridine In benzene 1.) RT, 12 h, 2.) reflux, 1 h; | 97% |
N,N'-dimethylbenzylamine
Methyltrichlorosilane
[2-(dimethylaminomethyl)phenyl]methyldichlorosilane
Conditions | Yield |
---|---|
With n-butyllithium; tetrachlorosilane In diethyl ether; hexane at 25℃; | 97% |
Conditions | Yield |
---|---|
With triethylamine In benzene | 97% |
Conditions | Yield |
---|---|
With triethylamine In benzene | 97% |
Conditions | Yield |
---|---|
With triethylamine In benzene for 2h; Heating; | 97% |
Conditions | Yield |
---|---|
With triethylamine In benzene for 2h; Heating; | 97% |
Methyltrichlorosilane
6-Dimethylsilanyl-hexan-2-ol
CH3Si(OCHCH3(CH2)4Si(CH3)2H)3
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 25℃; | 97% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 1.5h; | 97% |
Methyltrichlorosilane
N,N-dimethylamide O-SiMe3-(S)-lactic acid
Conditions | Yield |
---|---|
In hexane | 97% |
Methyltrichlorosilane
Conditions | Yield |
---|---|
With quinoline In benzene at 80℃; for 5h; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere; | 97% |
Methyltrichlorosilane
δ-chlorovaleronitrile
5-(dichloro-methyl-silanyl)-valeronitrile
Conditions | Yield |
---|---|
With magnesium; ethylene dibromide; manganese(ll) chloride In toluene at 70℃; for 4h; Solvent; Temperature; Inert atmosphere; | 96.7% |
3-Chloropropionitrile
Methyltrichlorosilane
dichloro(2-cyanoethyl)methylsilane
Conditions | Yield |
---|---|
With magnesium; ethylene dibromide; manganese(ll) chloride In tetrahydrofuran at 50℃; for 2h; Inert atmosphere; | 96.6% |
The Molecular Structure of Methyltrichlorosilane (CAS NO.75-79-6):
Empirical Formula: CH3Cl3Si
Molecular Weight: 149.479
IUPAC Name: trichloro(methyl)silane
Appearance: Colorless clear liquid
Nominal Mass: 148 Da
Average Mass: 149.479 Da
Monoisotopic Mass: 147.906959 Da
Index of Refraction: 1.434
Molar Refractivity: 29.94 cm3
Molar Volume: 114.9 cm3
Surface Tension: 21.1 dyne/cm
Density: 1.3 g/cm3
Enthalpy of Vaporization: 30.17 kJ/mol
Boiling Point: 73.5 °C at 760 mmHg
Vapour Pressure: 124 mmHg at 25°C
Storage temp: Flammables area
Water Solubility: REACTS
FreezingPoint: -77.8°C
Melting Point: -77°C
Flash Point: -13°C
Sensitive: Moisture Sensitive
Stability: Stable, but reacts violently with water. Highly flammable. Incompatible with moisture, water, strong bases, strong acids, strong oxidizing agents
InChI
InChI=1/CH3Cl3Si/c1-5(2,3)4/h1H3
Smiles
[Si](C)(Cl)(Cl)Cl
Synonyms: Methyl silicochloroform ; Methylsilicon trichloride ; Methylsilichloroform ; Methylsilyltrichloride
Product Categories: Chloro;Organics;Biochemistry;Functional Materials;Reagents for Oligosaccharide Synthesis;Si (Classes of Silicon Compounds);Si-Cl Compounds;Silane Coupling Agents;Silane Coupling Agents (Intermediates);Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Trichlorosilanes;Chloro Silanes
Methyltrichlorosilane (CAS NO.75-79-6) is mainly used a precursor for forming various cross-linked siloxane polymers. Methyltrichlorosilane (CAS NO.75-79-6) is mainly used to form polymers such as poly(methylsilyne). Esters and lactones can also be cleaved with methyltrichlorosilane and sodium iodide to give the corresponding carboxylic acids . Acetals convert to carbonyl compounds.Thus, Methyltrichlorosilane (CAS NO.75-79-6)can be used to remove acetal protecting groups from carbonyl compounds under mild conditions. Finally, Methyltrichlorosilane (CAS NO.75-79-6) and sodium iodide can be used as a means of converting alcohols to their corresponding iodides.
Methyltrichlorosilane (CAS NO.75-79-6) results from the "direct reaction" of chloromethane with elemental silicon in the presence of a copper catalyst, usually at a temperature of at least 250 °C.
3 CH3Cl + Si → CH3SiCl3 + C2H4 + H2
While this reaction is currently the standard in industrial silicone production and is nearly identical to the first direct synthesis of methyltrichlorosilane, the overall process is inefficient with respect to methyltrichlorosilane.
1. | skn-rbt 500 µL SEV | JACTDZ Journal of the American College of Toxicology. 12 (1993),571. | ||
2. | eye-rbt 5 mg/24H SEV | 85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,1219. | ||
3. | orl-rat LD50:1620 µL/kg | JACTDZ Journal of the American College of Toxicology. 12 (1993),571. | ||
4. | ihl-rat LC50:450 ppm/4H | 85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,1219. | ||
5. | ipr-rat LDLo:30 mg/kg | JIDHAN Journal of Industrial Hygiene. 30 (1948),332. | ||
6. | ihl-mus LC50:180 mg/m3/2H | TPKVAL Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Sciences. 3 (1961),23. | ||
7. | skn-rbt LD50:840 µL/kg | JACTDZ Journal of the American College of Toxicology. 12 (1993),571. |
Poison by inhalation and intraperitoneal routes. Moderately toxic by ingestion. A severe irritant to skin, eyes, and mucous membranes. Flammable when exposed to heat or flame; can react vigorously with oxidizing materials. When heated to decomposition it emits toxic fumes of Cl−. See also CHLOROSILANES.
Reported in EPA TSCA Inventory. EPA Extremely Hazardous Substances List.
Hazard Codes: FXi
Risk Statements: 11-14-36/37/38
R11: Highly flammable
R14: Reacts violently with water
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
Safety Statements: 26-39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S39: Wear eye / face protection
RIDADR: UN 1250 3/PG 1
WGK Germany: 1
RTECS: VV4550000
F: 10-21
F 10: Keep under argon
F 11: Keep under inert gas
HazardClass: 3
PackingGroup: I
DOT Classification: 3; Label: Flammable Liquid, Corrosive
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