Conditions | Yield |
---|---|
With trichloroisocyanuric acid In dichloromethane Heating; | 95.5% |
With copper(l) iodide; copper dichloride In diethyl ether at 20℃; for 3h; Inert atmosphere; | 94.2% |
With tellurium tetrachloride In benzene for 4.5h; Heating; | 90% |
With hydrogenchloride; ether adduct of tris(pentafluorophenyl)boron In toluene at 20℃; for 16h; Schlenk technique; Inert atmosphere; Cooling with liquid nitrogen; | 99 %Spectr. |
With dichloromethane; eosin y at 20℃; for 8h; Reagent/catalyst; Sealed tube; Inert atmosphere; Irradiation; Green chemistry; | 99 %Spectr. |
Conditions | Yield |
---|---|
With benzene In neat (no solvent) CH3SiHCl2 and C6H6 with a silylboron acid ester as catalyst at 200-210°C;; | 46% |
With C6H6; tris(trimethylsilyl)borate In neat (no solvent) (CH3)SiHCl2 and benzene at 200°C;; | 46% |
With benzene; tris(trimethylsilyl)borate In neat (no solvent) (CH3)SiHCl2 and benzene at 200°C;; | 46% |
Conditions | Yield |
---|---|
aluminium trichloride at 120℃; for 3h; in autoclave; | 25% |
tetramethylsilane
Phenyltrichlorosilane
A
chloro-trimethyl-silane
B
dichloromethylphenylsilane
Conditions | Yield |
---|---|
aluminium trichloride at 120℃; for 3h; Product distribution; in autoclave; | A 25% B 25% |
Conditions | Yield |
---|---|
With zirconium(IV) chloride |
Conditions | Yield |
---|---|
With diethyl ether | |
In tetrahydrofuran at 20℃; Kinetics; Further Variations:; Solvents; Reaction partners; | |
In tetrahydrofuran at 20℃; Kinetics; Further Variations:; Reaction partners; |
Conditions | Yield |
---|---|
at 400℃; unter Druck; | |
at 20 - 540℃; under 750.075 Torr; for 0.00138889h; Product distribution / selectivity; Gas phase; | |
With cleavable disilane at 540 - 590℃; under 750.075 Torr; for 0.00138889h; Product distribution / selectivity; Gas phase; | |
With dicumene at 590℃; under 750.075 Torr; for 0.00138889h; Product distribution / selectivity; Gas phase; |
bromobenzene
Methyltrichlorosilane
A
chloromethyldiphenylsilane
B
dichloromethylphenylsilane
Conditions | Yield |
---|---|
With magnesium 1) ether, 2) ether; Multistep reaction; |
Dichloromethylsilane
triphenylphosphine
A
phenylphosphane
B
diphenylphosphane
C
dichloromethylphenylsilane
Conditions | Yield |
---|---|
nickel Heating; | A n/a B n/a C 1.6 mol |
A
pentaphenylbenzene
B
dichloromethylphenylsilane
Conditions | Yield |
---|---|
In tetrachloromethane for 1.66667h; Irradiation; |
chloro(methyl)phenylsilane
A
methylphenylsilane
B
dichloromethylphenylsilane
Conditions | Yield |
---|---|
With tetrabutylammomium bromide at 120℃; for 24h; Equilibrium constant; Further Variations:; Temperatures; Disproportionation; |
Dichloromethylsilane
metaboric acid
benzene
A
Phenyltrichlorosilane
B
dichloromethylphenylsilane
Conditions | Yield |
---|---|
at 250℃; under 58840.6 Torr; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; Kinetics; Further Variations:; Solvents; Reaction partners; | |
In diethyl ether | |
In diethyl ether; toluene |
Methyltrichlorosilane
phenylmagnesium chloride
chlorobenzene
A
chloromethyldiphenylsilane
B
dichloromethylphenylsilane
Conditions | Yield |
---|---|
In diethyl ether at 64℃; for 0.166667h; Product distribution / selectivity; Grignard Reaction; |
Methyltrichlorosilane
phenylmagnesium chloride
A
diphenylsilyl chloride
B
dichloromethylphenylsilane
Conditions | Yield |
---|---|
In diethyl ether; toluene at 58℃; for 0.225h; Product distribution / selectivity; Grignard Reaction; | A 17.5 %Chromat. B 5.7 %Chromat. |
chloro-trimethyl-silane
diethyl ether
phenylmagnesium chloride
A
dichloro(ethyl)methylsilane
B
biphenyl
C
ethoxy(methyl)dichlorosilane
D
methyldiphenylsilane
E
chloro(methyl)phenylsilane
F
chloromethyldiphenylsilane
G
chlorobenzene
H
benzene
I
dichloromethylphenylsilane
Conditions | Yield |
---|---|
In toluene at 61 - 62℃; for 0.316667 - 0.35h; Product distribution / selectivity; |
chloro-trimethyl-silane
diethyl ether
phenylmagnesium chloride
A
biphenyl
B
methyldiphenylsilane
C
chloro(methyl)phenylsilane
D
chloromethyldiphenylsilane
E
chlorobenzene
F
toluene
G
benzene
H
dichloromethylphenylsilane
Conditions | Yield |
---|---|
In n-heptane at 58 - 59℃; for 0.35 - 0.366667h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With chlorobenzene In neat (no solvent) (CH3)SiHCl2 and C6H5Cl at 450°C;; | |
With chlorobenzene In neat (no solvent) (CH3)SiHCl2 and C6H5Cl at 450°C;; |
methyl pentachlorodisilane
A
Phenyltrichlorosilane
B
dichloromethylphenylsilane
Conditions | Yield |
---|---|
With chlorobenzene In neat (no solvent) passing (CH3)Cl2SiSiCl3 and C6H5Cl through a tube at 520°C;; |
Conditions | Yield |
---|---|
With methylene chloride; benzene; copper In neat (no solvent) Si-Cu and a mixt. of CH3Cl and C6H6 at 350°C;; | |
With methylene chloride; benzene; copper In neat (no solvent) Si-Cu and a mixt. of CH3Cl and C6H6 at 350°C;; |
Conditions | Yield |
---|---|
aluminium trichloride In neat (no solvent) (CH3)3SiCl and (C6H5)SiCl3 at 325°C;; | |
aluminium trichloride In neat (no solvent) (CH3)3SiCl and (C6H5)SiCl3 at 325°C;; |
tetrachlorosilane
dichloromethylphenylsilane
Conditions | Yield |
---|---|
With CH3MgBr; C6H5MgBr In not given |
bromobenzene
1,1,2,2-tetrachloro-1,2-dimethyldisilane
A
chloromethyldiphenylsilane
B
diphenylsilyl dichloride
C
dichloromethylphenylsilane
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) at 160℃; for 24h; Inert atmosphere; neat (no solvent); |
1,1,2,2-tetrachloro-1,2-dimethyldisilane
chlorobenzene
A
chloromethyldiphenylsilane
B
diphenylsilyl dichloride
C
dichloromethylphenylsilane
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) at 160℃; for 24h; Inert atmosphere; neat (no solvent); |
Dichloromethylsilane
benzene
A
Methyltrichlorosilane
B
dichloromethylphenylsilane
Conditions | Yield |
---|---|
With 20percent Boria / 80percent Alumina - Graphite Binder at 250℃; under 77.5728 Torr; for 4h; Pressure; Reagent/catalyst; Time; Sealed tube; | A 6.74 %Chromat. B 25.44 %Chromat. |
phenyl(chloromethyl)dihydrosilane
dichloromethylphenylsilane
Conditions | Yield |
---|---|
With dichloromethane; eosin y at 20℃; for 4h; Reagent/catalyst; Inert atmosphere; Green chemistry; | 99 %Spectr. |
Conditions | Yield |
---|---|
Stage #1: bromobenzene With magnesium In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; Stage #2: Methyltrichlorosilane In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere; Schlenk technique; |
Conditions | Yield |
---|---|
With potassium hydroxide; palladium on activated charcoal In water at 100℃; | 100% |
With potassium hydroxide; palladium on activated charcoal In water Heating; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide; palladium on activated charcoal In water Heating; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide; palladium on activated charcoal In water Heating; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide; palladium on activated charcoal In water Heating; | 100% |
2-hydroxybromobenzene
1-bromo-2-(phenylethenyl)benzene
dichloromethylphenylsilane
Conditions | Yield |
---|---|
Stage #1: 1-bromo-2-(phenylethenyl)benzene With tert.-butyl lithium In tetrahydrofuran; pentane at -70℃; for 0.416667h; Schlenk technique; Inert atmosphere; Stage #2: dichloromethylphenylsilane In tetrahydrofuran; pentane at -70 - 20℃; for 7.58333h; Schlenk technique; Inert atmosphere; Stage #3: 2-hydroxybromobenzene In tetrahydrofuran; pentane at 35℃; for 48h; Schlenk technique; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; | 99% |
In hexane for 12h; Inert atmosphere; | 94.2% |
n-octyne
dichloromethylphenylsilane
methyldi(oct-1-yn-1-yl)(phenyl)silane
Conditions | Yield |
---|---|
Stage #1: n-octyne With n-butyllithium In tetrahydrofuran-d8 at -78℃; for 0.5h; Inert atmosphere; Stage #2: dichloromethylphenylsilane In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: allyl bromide With indium In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: dichloromethylphenylsilane In N,N-dimethyl-formamide at 20℃; for 3h; | 98% |
With zinc In tetrahydrofuran for 0.166667h; Inert atmosphere; Sonication; | 78% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 19h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 110℃; for 1.5h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With pyridine In diethyl ether for 8h; Heating; | 97% |
5-bromo-1-methyl-1H-pyrrole-2-carboxylic acid
dichloromethylphenylsilane
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; Silylation; Electrochemical reaction; | 97% |
ethyl cinnamate
dichloromethylphenylsilane
3,3-diphenyl-propionic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: dichloromethylphenylsilane With potassium carbonate In toluene at 20℃; for 2h; Stage #2: ethyl cinnamate With water; [Rh(OH)(cod)]2 In toluene at 120℃; for 41h; | 97% |
allylsamarium bromide
dichloromethylphenylsilane
diallyl(methyl)(phenyl)silane
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 2h; | 97% |
3-Bromo-but-1-yne
dichloromethylphenylsilane
di-(buta-1,2-dienyl)methylphenylsilane
Conditions | Yield |
---|---|
Stage #1: 3-Bromo-but-1-yne With indium In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: dichloromethylphenylsilane In N,N-dimethyl-formamide at 20℃; for 3h; | 97% |
propargyl bromide
dichloromethylphenylsilane
diallenylmethylphenylsilane
Conditions | Yield |
---|---|
Stage #1: propargyl bromide With indium In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: dichloromethylphenylsilane In N,N-dimethyl-formamide at 20℃; for 3h; | 97% |
1-Heptyne
dichloromethylphenylsilane
di(hept-1-yn-1-yl)(methyl)(phenyl)silane
Conditions | Yield |
---|---|
Stage #1: 1-Heptyne With n-butyllithium In tetrahydrofuran-d8 at -78℃; for 0.5h; Inert atmosphere; Stage #2: dichloromethylphenylsilane In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; | 97% |
dichloromethylphenylsilane
Conditions | Yield |
---|---|
In methanol; benzene Heating; | 96% |
1,3-diallyl-4-(trimethylsilyloxy)-2,6-dioxo-1,3,5-triazine
dichloromethylphenylsilane
Conditions | Yield |
---|---|
at 120 - 160℃; | 95% |
phenylacetylene
dichloromethylphenylsilane
bis(phenylethynylene)methylphenylsilane
Conditions | Yield |
---|---|
With [{Ir(μ-Cl)(CO)2}2]; N-ethyl-N,N-diisopropylamine; lithium iodide at 90℃; for 24h; Schlenk technique; Inert atmosphere; | 95% |
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran-d8 at -78℃; for 0.5h; Inert atmosphere; Stage #2: dichloromethylphenylsilane In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; | 85% |
In various solvent(s) electrolysis; | 56% |
Stage #1: phenylacetylene With n-butyllithium Stage #2: dichloromethylphenylsilane | |
With n-butyllithium In tetrahydrofuran at -78℃; |
Conditions | Yield |
---|---|
With air; sodium fluoride; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate at 100℃; for 12h; | 95% |
Stage #1: dichloromethylphenylsilane With potassium carbonate In toluene at 20℃; for 2h; Stage #2: cyclohexenone With water; [Rh(OH)(cod)]2 In toluene at 120℃; for 24h; | 70% |
allylsamarium bromide
dichloromethylphenylsilane
allylchloro(methyl)phenylsilane
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 1h; | 95% |
trimethylsilylacetylene
dichloromethylphenylsilane
bis(trimethylsilylethynyl)phenyl(methyl)silane
Conditions | Yield |
---|---|
With [{Ir(μ-Cl)(CO)2}2]; N-ethyl-N,N-diisopropylamine; lithium iodide at 90℃; for 24h; Schlenk technique; Inert atmosphere; | 95% |
Methyltrichlorosilane
phenylmagnesium chloride
chlorobenzene
dichloromethylphenylsilane
chloromethyldiphenylsilane
Conditions | Yield |
---|---|
In diethyl ether at 67℃; for 0.166667h; Product distribution / selectivity; Grignard Reaction; | 94.11% |
Conditions | Yield |
---|---|
With sodium tetrafluoroborate In various solvent(s) for 0.75h; Heating; | 94% |
With zinc(II) fluoride | |
With potassium hydrogen bifluoride |
dichloromethylphenylsilane
Conditions | Yield |
---|---|
In methanol; benzene Heating; | 94% |
2-bromofuran
dichloromethylphenylsilane
di(2-furyl)(methyl)phenylsilane
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide 2:1 substrate/PhMeSiCl2 ratio, electrochemical conditions (Mg anode, 2.2 F.mol-1); | 94% |
1-Bromo-2-butyne
dichloromethylphenylsilane
di-(1-methylallenyl)methylphenylsilane
Conditions | Yield |
---|---|
Stage #1: 1-Bromo-2-butyne With indium In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: dichloromethylphenylsilane In N,N-dimethyl-formamide at 20℃; for 3h; | 94% |
2-bromo-1-(trimethylsilylethynyl)benzene
allylmagnesium bromide
dichloromethylphenylsilane
Conditions | Yield |
---|---|
Stage #1: 2-bromo-1-(trimethylsilylethynyl)benzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: dichloromethylphenylsilane In tetrahydrofuran at -78 - 50℃; for 6h; Stage #3: allylmagnesium bromide Further stages; | 94% |
Reported in EPA TSCA Inventory. EPA Extremely Hazardous Substances List.
DOT Classification: 8; Label: Corrosive
The Dichloromethylphenylsilane, with the CAS registry number 149-74-6, is also known as Phenylmethyldichlorosilane. It belongs to the product categories of Organosilicon Reagents; Dichlorosilanes; Dichlorosilanes (for Polysilanes); Functional Materials; Reagent for High-Performance Polymer Research; Si (Classes of Silicon Compounds); Si-Cl Compounds. Its EINECS registry number is 205-746-2. Its IUPAC name is called dichloro-methyl-phenylsilane. This chemical is clear colourless liquid which should be sealed in a dry cool place. Its classification code is Organometallic. What's more, it can be used in the synthesis of organic silicon and is one of important monomer in organic silicon synthesis .
Physical properties of Dichloromethylphenylsilane: (1)ACD/LogP: 4.94; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.94; (4)ACD/LogD (pH 7.4): 4.94; (5)ACD/BCF (pH 5.5): 3316.78; (6)ACD/BCF (pH 7.4): 3316.78; (7)ACD/KOC (pH 5.5): 11527.18; (8)ACD/KOC (pH 7.4): 11527.18; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.514; (13)Molar Refractivity: 49.8 cm3; (14)Molar Volume: 165.2 cm3; (15)Surface Tension: 28.4 dyne/cm; (16)Density: 1.15 g/cm3; (17)Flash Point: 73.2 °C; (18)Enthalpy of Vaporization: 42.32 kJ/mol; (19)Boiling Point: 205 °C at 760 mmHg; (20)Vapour Pressure: 0.366 mmHg at 25°C.
Uses of Dichloromethylphenylsilane: it can be used to produce dimethoxy-methyl-phenyl-silane at temperature of 7-10 °C. This reaction will need reagent pyridine and solvent benzene. The yield is about 86%.
When you are using this chemical, please be cautious about it as the following:
This chemical may destroy living tissue on contact. It reacts violently with water. In addition, it also may cause burns. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C[Si](C1=CC=CC=C1)(Cl)Cl
(2)InChI: InChI=1S/C7H8Cl2Si/c1-10(8,9)7-5-3-2-4-6-7/h2-6H,1H3
(3)InChIKey: GNEPOXWQWFSSOU-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mammal (species unspecified) | LC50 | inhalation | 150mg/m3 (150mg/m3) | LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA LIVER: FATTY LIVER DEGERATION BLOOD: OTHER CHANGES | Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 3, Pg. 81, 1961. |
mouse | LCLo | inhalation | 30mg/m3/2H (30mg/m3) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LIVER: FATTY LIVER DEGERATION BLOOD: CHANGES IN SPLEEN | Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 3, Pg. 61, 1961. |
mouse | LDLo | intraperitoneal | 100mg/kg (100mg/kg) | Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 3, Pg. 81, 1961. | |
mouse | LDLo | subcutaneous | 100mg/kg (100mg/kg) | Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 3, Pg. 81, 1961. | |
rat | LDLo | intraperitoneal | 100mg/kg (100mg/kg) | Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 3, Pg. 81, 1961. |
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