Conditions | Yield |
---|---|
In toluene at 65℃; for 4h; Solvent; Inert atmosphere; Glovebox; | A n/a B 86% |
methylmagnesium bromide
sodium bis(benzene-1,2-diolatophenyl)silicate
A
trimethylphenylsilane
B
Dimethylphenylsilane
C
phenylsilane
D
methylphenylsilane
Conditions | Yield |
---|---|
In diethyl ether at 35℃; for 2h; | A 3% B 85% C 6% D 6% |
In diethyl ether at 35℃; for 2h; Product distribution; other organometallic compound; var. ratios; | A 3% B 85% C 6% D 6% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether | 84% |
With lithium aluminium tetrahydride Reduction; | 74% |
With lithium aluminium tetrahydride; diethyl ether |
methyllithium
sodium bis(benzene-1,2-diolatophenyl)silicate
A
trimethylphenylsilane
B
Dimethylphenylsilane
C
phenylsilane
D
methylphenylsilane
Conditions | Yield |
---|---|
In diethyl ether at 35℃; for 2h; | A 4% B 81% C 12% D 4% |
In tetrahydrofuran at 60℃; for 2h; | A 32% B 49% C 9% D 10% |
methylmagnesium bromide
sodium bis(benzene-1,2-diolatophenyl)silicate
A
Dimethylphenylsilane
B
phenylsilane
C
methylphenylsilane
Conditions | Yield |
---|---|
In diethyl ether at 0℃; for 2.5h; | A 12% B 79% C 9% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 2h; | 72% |
With lithium aluminium tetrahydride Yield given; |
Conditions | Yield |
---|---|
In not given | 69% |
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; ethyl bromide; tetraoctyl ammonium bromide In benzene-d6 at 20℃; for 24h; | 49% |
With Y(3+)*2C12H21Si(1-)*H(1-)*C4H8O; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene-d6 at 80℃; for 12h; | 8% |
phenylchlorosilane
A
1,2-diphenyldisilane
B
1,2,3-triphenyltrisilane
C
phenylsilane
D
diphenylsilane
Conditions | Yield |
---|---|
With Mg-anode; stainless steel cathode In tetrahydrofuran for 29h; Electrolysis; | A 38% B n/a C n/a D n/a |
Phenyltrichlorosilane
A
dichlorophenylsilane
B
phenylsilane
C
phenylchlorosilane
Conditions | Yield |
---|---|
With sodium hydride; lithium chloride In diethylene glycol dimethyl ether at 160℃; for 14h; Inert atmosphere; | A 33% B 19% C 38% |
With diisobutylaluminium hydride In toluene Solvent; |
phenylchlorosilane
A
1,2-diphenyldisilane
B
phenylsilane
C
diphenylsilane
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran; hexane at 20℃; for 2h; | A 30% B n/a C n/a |
Conditions | Yield |
---|---|
With dihydrogen hexachloroplatinate |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether Heating; | |
With lithium aluminium tetrahydride In diethyl ether | |
With lithium aluminium tetrahydride In diethyl ether at 20℃; |
Conditions | Yield |
---|---|
beim Erhitzen; |
Conditions | Yield |
---|---|
beim Erhitzen; |
Trimethylsilanol
tris(2-pyridylthio)methyl zinc hydride
phenylsilane
dmap
[[MeC(N(2,6-iPr2C6H3))CHC(Me)(NCH2CH2NMe)]Sc(H)(N(2,6-iPr2C6H3)(SiH2Ph))]
A
[[MeC(N(2,6-iPr2C6H3))CHC(Me)(NCH2CH2NMe)]Sc=N(2,6-iPr2C6H3)(DMAP)]
B
phenylsilane
Conditions | Yield |
---|---|
In benzene-d6 at 25℃; for 1h; Equilibrium constant; Inert atmosphere; |
Conditions | Yield |
---|---|
With diisobutylaluminium hydride |
Conditions | Yield |
---|---|
In benzene-d6 at 25℃; for 24h; Thermodynamic data; Equilibrium constant; Temperature; Inert atmosphere; | A n/a B 48.5 %Spectr. |
Conditions | Yield |
---|---|
In benzene-d6 at 25℃; for 20h; Thermodynamic data; Equilibrium constant; Temperature; Inert atmosphere; |
phenylsilane
Conditions | Yield |
---|---|
With tris(pentafluorophenyl)borate In dichloromethane-d2 at 20℃; for 19h; Catalytic behavior; Glovebox; Sealed tube; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: bis(tri-t-butylphosphine)palladium(0); diisopropylamine / benzene / 24 h / 20 °C / Glovebox; Sealed tube 2: tris(pentafluorophenyl)borate / dichloromethane-d2 / 19 h / 20 °C / Glovebox; Sealed tube View Scheme |
dimethoxy(diphenyl)silane
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
A
phenylsilane
B
diphenylsilane
Conditions | Yield |
---|---|
With (η5-C5Me4SiMe3)2YH(thf) In benzene-d6 at 100℃; for 24h; Inert atmosphere; | A 12 %Spectr. B 40 %Spectr. |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: magnesium / tetrahydrofuran / Reflux 2: lithium aluminium tetrahydride / diethyl ether / 0 °C View Scheme |
Conditions | Yield |
---|---|
In benzene at 22.84℃; under 760.051 Torr; for 18h; Equilibrium constant; Kinetics; Temperature; Inert atmosphere; |
Conditions | Yield |
---|---|
With Et2OFe(catecholate-porous organic polymer) In benzene-d6 at 23℃; for 0.0833333h; | 100% |
Conditions | Yield |
---|---|
With Et2OFe(catecholate-porous organic polymer) In benzene-d6 at 23℃; for 0.0333333h; | 100% |
Wilkinson's catalyst | |
Rh catalyst |
Conditions | Yield |
---|---|
With <(CH3)5>2YCH3*THF In cyclohexane for 1h; Mechanism; Ambient temperature; other dienes; other silanes; | 100% |
With (C5Me5)2YCH3*THF In cyclohexane for 1h; Ambient temperature; | 100% |
With <(CpTMS)2YMe>2 In cyclohexane for 4h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With C16H11BrMnN3O3 In tetrahydrofuran at 100℃; for 3h; Reagent/catalyst; Solvent; Time; Inert atmosphere; Sealed tube; Heating; chemoselective reaction; | 100% |
bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (S,S)-2,2''-bis{(R)-1-(di-n-butylphosphino)ethyl}-1,1''-biferrocene In tetrahydrofuran at -40℃; for 48h; hydrosilylation; | |
With C16H25AlBN6(1+)*C19H3BF15(1-) In chloroform-d1 at 75℃; for 1.5h; |
Conditions | Yield |
---|---|
for 0.166667h; Substitution; | 100% |
Conditions | Yield |
---|---|
With Et2OFe(catecholate-porous organic polymer) In benzene-d6 at 23℃; for 0.0333333h; | 100% |
With [{(DIPP-nacnac)CaH(thf)}2] In benzene-d6 at 50℃; for 34h; chemoselective reaction; | 95 %Chromat. |
With [N,N'-(2,6-pyridinediyldiethylidyne)bis[3-(diphenylphosphino)-1-propanamine]]MnH under 760.051 Torr; for 0.0666667h; Glovebox; Inert atmosphere; | |
With tris(2-pyridylthio)methyl zinc hydride In benzene-d6 at 20℃; for 0.75h; Catalytic behavior; Inert atmosphere; |
Conditions | Yield |
---|---|
With Et2OFe(catecholate-porous organic polymer) In benzene-d6 at 23℃; for 0.0333333h; Concentration; Time; | 100% |
With C29H30N5PZn In benzene-d6 at 25℃; for 6h; Inert atmosphere; |
Conditions | Yield |
---|---|
With MesPDI; cobalt(II) stearate In tetrahydrofuran at 60℃; for 5h; Reagent/catalyst; | 100% |
With C22H31Cl2CoN2P In neat (no solvent) at 60℃; for 24h; Reagent/catalyst; Temperature; Sealed tube; Inert atmosphere; regioselective reaction; | 92% |
With 2,6-bis[1-(2,4,6-trimethylimino)ethyl]pyridine; C10H14CoO5 In toluene at 60℃; for 24h; Reagent/catalyst; Temperature; regioselective reaction; | 91% |
With 2,6-bis[1-(2,4,6-trimethylimino)ethyl]pyridine; cobalt(II) tetrafluoroborate hexahydrate In tetrahydrofuran at 20℃; for 4h; Catalytic behavior; Reagent/catalyst; regioselective reaction; | 72 %Spectr. |
Conditions | Yield |
---|---|
In tetrahydrofuran for 17h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With barium hexamethyldisilazide tetrahydrofuranate In benzene-d6 at 60℃; for 10h; Kinetics; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube; chemoselective reaction; | 100% |
Conditions | Yield |
---|---|
With C22H28N2; cobalt(II) acetate In tetrahydrofuran at 30℃; for 3h; Catalytic behavior; Temperature; Inert atmosphere; | 100% |
With lithium triethylborohydride; C12H12Cl2CoN6 In tetrahydrofuran at 40℃; for 20h; Schlenk technique; Inert atmosphere; regioselective reaction; | 99% |
With ethylmagnesium bromide; C84H104Cl2FeN2 In tetrahydrofuran at 0℃; for 3h; Glovebox; Inert atmosphere; Schlenk technique; regioselective reaction; | 92% |
Conditions | Yield |
---|---|
In benzene-d6 at 60℃; for 96h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With dichloromethane; eosin y at 30℃; Flow reactor; Inert atmosphere; Irradiation; Green chemistry; | 99% |
With hydrogenchloride In diethyl ether at 80℃; for 35.25h; Temperature; Solvent; | 97% |
With copper(l) iodide; copper dichloride In diethyl ether at 20℃; for 2h; Inert atmosphere; | 91.7% |
Conditions | Yield |
---|---|
With dichloromethane; eosin y at 50℃; Reagent/catalyst; Temperature; Flow reactor; Inert atmosphere; Irradiation; Green chemistry; | 99% |
With trichloroisocyanuric acid In dichloromethane for 5h; Heating; | 97.5% |
With copper(l) iodide; copper dichloride In diethyl ether at 20℃; for 4h; Inert atmosphere; | 92.9% |
With tellurium tetrachloride In benzene for 6h; Heating; | 75% |
Conditions | Yield |
---|---|
With C66H106N4O6Sm2 In toluene at 60℃; for 1h; Catalytic behavior; Solvent; Temperature; Inert atmosphere; Glovebox; Schlenk technique; regioselective reaction; | 99% |
With Me2SiCp''2CH(SiMe3)2 In benzene for 48h; Ambient temperature; | 96% |
With C18H19N3Ni(1+)*C32H12BF24(1-) In 1,2-dichloro-ethane at 60℃; for 4h; Inert atmosphere; | 96.7% |
Conditions | Yield |
---|---|
With tris((4,4-dimethyl-2-oxazolinyl)phenylborate) MgMe In benzene at 20℃; for 24h; Inert atmosphere; | 99% |
With [(Et2N)3U][BPh4] In benzene for 10h; Substitution; Heating; | 86.5% |
With C18H54LaN3Si6*2C4H8O In benzene-d6 at 25℃; for 0.166667h; Inert atmosphere; | 85 %Spectr. |
Conditions | Yield |
---|---|
With tris((4,4-dimethyl-2-oxazolinyl)phenylborate) MgMe In benzene at 20℃; for 24h; Inert atmosphere; | 99% |
With C36H70N8O2Si4Y2 In toluene at 20℃; for 0.25h; Glovebox; Schlenk technique; | 92% |
at 20℃; for 56h; Substitution; |
Conditions | Yield |
---|---|
With C31H52N2PSi4Y In benzene-d6 at 25℃; for 1h; Reagent/catalyst; Glovebox; Inert atmosphere; | 99% |
With C36H70N8O2Si4Y2 In toluene at 20℃; for 0.25h; Glovebox; Schlenk technique; | 96% |
With [(Et2N)3U][BPh4] In benzene for 7h; Substitution; | 94.8% |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran | 99% |
With n-butyllithium In tetrahydrofuran | 0.304g (1.55 mmol, 80%) |
dimethylbis(η5-pentamethylcyclopentadienyl)thorium
3-methyl-but-1-yne
phenylsilane
((CH3)5C5)2Th(CCCH(CH3)2)[C(C6H5SiH2)CH(CH(CH3)2)]
Conditions | Yield |
---|---|
In benzene stirring (room temp., 12 h), PhSiH3 addn., stirring (6 h); elem. anal.; | 99% |
dimethylbis(η5-pentamethylcyclopentadienyl)uranium
3-methyl-but-1-yne
phenylsilane
((CH3)5C5)2U(CCCH(CH3)2)(C((C6H5)SiH2)C(H)CH(CH3)2)
Conditions | Yield |
---|---|
In benzene stirring (4 h), PhSiH3 addn., stirring (6 h); elem. anal.; | 99% |
Conditions | Yield |
---|---|
In toluene under N2; to a stirred soln. of Ta-contg. compd. (0.350 mmol) in toluenewas added phenylsilane (0.350 mmol) in the same solvent; stirring for 2 4 h at -40°C; solvent was removed under vac.; the residue was triturated under hexanesand left overnight; the ppt. was recovered on a glass frit; elem. anal.; | 99% |
[(phenyl)B(CH2P(iPr)2)3(methyl)iron(II)]
phenylsilane
[iron(II)(phenyl)B(CH2P(iPr)2)3(hydride)(η3-H2Si(methylphenyl))]
Conditions | Yield |
---|---|
In benzene reactn. of Fe compex with C6H5SiH3 at room temp. for 30 min; detd. by (1)H NMR; | 99% |
Conditions | Yield |
---|---|
In diethyl ether for several weeks at -20°C; | 99% |
Conditions | Yield |
---|---|
In not given byproducts: CH4, C6H5SiH2CH3; at -20°C for 4 h; | 99% |
Conditions | Yield |
---|---|
With [Fe(nacnac)dippCH2SiMe3] In benzene-d6 at 20℃; for 48h; | 99% |
With tris((4,4-dimethyl-2-oxazolinyl)phenylborate) MgMe In benzene at 20℃; for 24h; Inert atmosphere; | 97% |
With [IMesMg(2,4,6-Me3C6H2){N(SiMe3)2}] In benzene at 20℃; for 15h; Inert atmosphere; Schlenk technique; Glovebox; |
phenylsilane
1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene
1-phenyl-2,5-bis-(2,6-diisopropylphenyl)-3,4-dehydro-2,5-diazasilinane
Conditions | Yield |
---|---|
at 160℃; for 5h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With C27H36Cl2N2Zn at 100℃; for 20h; | 99% |
phenylsilane
tert-butyl(hex-5-enyloxy)diphenylsilane
Conditions | Yield |
---|---|
With (tBuPNNiPr)FeCl2; sodium triethylborohydride In toluene at -34 - 20℃; for 8h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In neat liquid at 30℃; for 1h; Catalytic behavior; Kinetics; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; chemoselective reaction; | 99% |
With silver at 20℃; for 2h; | 97% |
With palladium In tetrahydrofuran at 20℃; for 4h; | 95% |
Product Name: Phenylsilane
Molecular Structure:
Molecular Formula : C6H5SiH3
Molecular Weight: 108.21
CAS NO: 694-53-1
EINECS : 211-772-5
Density: 0.877
Boiling point: 120 ºC
Melting point: -64 to -68°C
Flash point: 8 ºC
Enthalpy of Vaporization: 34.27 kJ/mol
Boiling Point: 119.3 °C at 760 mmHg
Vapour Pressure: 19.2 mmHg at 25°C
Refractive index n20/D 1.510(lit.)
Storage temp: Flammables area
Sensitive: Air & Moisture Sensitive
Appearance: Silylbenzene (CAS NO. 694-53-1) is clear colorless liquid
Silylbenzene (CAS NO. 694-53-1) is used as organic reagents and pharmaceutical intermediates.
1. | orl-mus LD50:700 mg/kg | 85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,1227. | ||
2. | ihl-mus LC50:14,500 mg/m3/2H | 85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,1227. |
Reported in EPA TSCA Inventory.
Hazard CodesF ,Xn
Risk Statements 11-14-15-20/22-36/37/38
R11:Highly flammable.
R14 :Reacts violently with water.
R15:Contact with water liberates extremely flammable gases.
R20/22:Harmful by inhalation and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 16-43
S16:Keep away from sources of ignition.
S43:In case of fire use ... (there follows the type of fire-fighting equipment to be used.)
RIDADR UN 3399 4.3/PG 2
WGK Germany 1
RTECS VV4825000
F 10-21
TSCA Yes
HazardClass 4.3
PackingGroup II
1.General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Vapors can travel to a source of ignition and flash back. Will burn if involved in a fire. Water Reactive. Material will react with water and may release a flammable and/or toxic gas. Flammable liquid and vapor.
2.Extinguishing Media: Use foam, dry chemical, or carbon dioxide. DO NOT USE WATER!
3.Handling: Use spark-proof tools and explosion proof equipment. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
4.Storage: Keep Silylbenzene (CAS NO. 694-53-1) away from heat, sparks, and flame. Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container. Keep under a nitrogen blanket. Flammables-area.
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