Home Cart 0 Sign in  

[ CAS No. 778-24-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 778-24-5
Chemical Structure| 778-24-5
Structure of 778-24-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 778-24-5 ]

Related Doc. of [ 778-24-5 ]

Alternatived Products of [ 778-24-5 ]

Product Details of [ 778-24-5 ]

CAS No. :778-24-5 MDL No. :MFCD00041326
Formula : C14H16Si Boiling Point : -
Linear Structure Formula :- InChI Key :WJKVFIFBAASZJX-UHFFFAOYSA-N
M.W : 212.36 Pubchem ID :136618
Synonyms :

Calculated chemistry of [ 778-24-5 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 69.63
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.9
Log Po/w (XLOGP3) : 4.85
Log Po/w (WLOGP) : 2.51
Log Po/w (MLOGP) : 4.41
Log Po/w (SILICOS-IT) : 2.77
Consensus Log Po/w : 3.49

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.67
Solubility : 0.00452 mg/ml ; 0.0000213 mol/l
Class : Moderately soluble
Log S (Ali) : -4.58
Solubility : 0.00553 mg/ml ; 0.0000261 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.8
Solubility : 0.000337 mg/ml ; 0.00000159 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.75

Safety of [ 778-24-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 778-24-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 778-24-5 ]

[ 778-24-5 ] Synthesis Path-Downstream   1~87

  • 1
  • [ 778-24-5 ]
  • [ 4095-10-7 ]
YieldReaction ConditionsOperation in experiment
With bromine
  • 3
  • [ 778-24-5 ]
  • [ 18408-63-4 ]
YieldReaction ConditionsOperation in experiment
With nickel; methyl cyclohexane Hydrogenation;
  • 6
  • [ 75-78-5 ]
  • [ 108-90-7 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: chlorobenzene With gallium(III) trichloride; magnesium Stage #2: dimethylsilicon dichloride In chlorobenzene at 70℃; for 8.5h; Further stages.;
With sodium
  • 7
  • [ 78-62-6 ]
  • [ 108-90-7 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
With sodium
  • 8
  • [ 917-64-6 ]
  • [ 80-10-4 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether Erhitzen des Reaktionsprodukts auf 150grad;
  • 9
  • [ 4353-77-9 ]
  • [ 778-24-5 ]
  • Dimethylsilyl-bis-benzolsulfonat [ No CAS ]
  • 11
  • [ 1145-98-8 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
With dimethyl sulfoxide In 1,4-dioxane at 5℃; Irradiation;
  • 12
  • [ 67-56-1 ]
  • [ 37865-47-7 ]
  • [ 17881-88-8 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
1: 14% 2: 54% In cyclohexane for 1h; Ambient temperature; Irradiation;
  • 13
  • [ 1066-35-9 ]
  • phenylmagnesium chloride [ No CAS ]
  • [ 766-77-8 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
1: 11.5% 2: 83.4% In tetrahydrofuran at 90℃; for 1h;
  • 14
  • [ 1493-13-6 ]
  • [ 778-24-5 ]
  • [ 99542-59-3 ]
YieldReaction ConditionsOperation in experiment
In chloroform-d1
  • 15
  • [ 766-77-8 ]
  • phenylmagnesium chloride [ No CAS ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
3.9% In tetrahydrofuran at 50℃; for 2h;
  • 16
  • [ 62383-81-7 ]
  • [ 778-24-5 ]
  • [ 124081-20-5 ]
  • [ 124081-31-8 ]
YieldReaction ConditionsOperation in experiment
With tin(IV) chloride; nickel 1.) CH2Cl2, RT, 30 min; Multistep reaction. Title compound not separated from byproducts;
  • 17
  • [ 62383-81-7 ]
  • [ 778-24-5 ]
  • [ 124081-19-2 ]
  • [ 124081-17-0 ]
YieldReaction ConditionsOperation in experiment
With tin(IV) chloride In dichloromethane for 0.5h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
  • 18
  • [ 778-24-5 ]
  • [ 768-33-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In dichloromethane
  • 19
  • [ 37865-47-7 ]
  • [ 17881-88-8 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
1: 54% 2: 14% With methanol In cyclohexane for 1h; Ambient temperature; Irradiation;
  • 20
  • phenylmagnesium bromide [ No CAS ]
  • [ 79035-76-0 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
50 % Chromat. In tetrahydrofuran 1.) -78 deg C, 30 min, 2.) RT, 1 h;
  • 21
  • [ 100-42-5 ]
  • [ 661-68-7 ]
  • [ 591-51-5 ]
  • [ 62257-76-5 ]
  • [ 778-24-5 ]
  • [ 128756-74-1 ]
  • [ 129165-25-9 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine)platinum In benzene at 150℃; for 22h; other alkene;
  • 22
  • [ 591-51-5 ]
  • [ 90185-40-3 ]
  • [ 766-77-8 ]
  • [ 778-24-5 ]
  • [ 128756-77-4 ]
  • [ 82877-25-6 ]
YieldReaction ConditionsOperation in experiment
1: 34 % Chromat. 2: 19 % Chromat. 3: 3 % Chromat. 4: 13 % Chromat. In tetrahydrofuran; hexane at -30 - 25℃; for 1h;
1: 34 % Chromat. 2: 19 % Chromat. 3: 21 % Chromat. 4: 3 % Chromat. In tetrahydrofuran; hexane at -30 - 25℃; for 1h;
  • 23
  • [ 591-51-5 ]
  • [ 82877-25-6 ]
  • [ 778-24-5 ]
  • [ 128756-77-4 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; hexane at -30 - 25℃; for 1h;
  • 24
  • [ 113800-12-7 ]
  • [ 778-24-5 ]
  • [ 103-29-7 ]
YieldReaction ConditionsOperation in experiment
1: 12 % Chromat. 2: 16 % Chromat. With acetophenone In benzene at 20℃; Irradiation;
  • 26
  • [ 87938-59-8 ]
  • [ 13688-68-1 ]
  • [ 778-24-5 ]
  • 27
  • [ 778-24-5 ]
  • [ 13247-99-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide
  • 28
  • [ 1145-98-8 ]
  • [ 622-29-7 ]
  • [ 766-77-8 ]
  • [ 778-24-5 ]
  • [1-[2-(Dimethyl-phenyl-silanyl)-phenyl]-meth-(E)-ylidene]-methyl-amine [ No CAS ]
  • [1-[2,6-Bis-(dimethyl-phenyl-silanyl)-phenyl]-meth-(E)-ylidene]-methyl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 15% 2: 15% In toluene at 160℃; for 120h; Further byproducts given. Yields of byproduct given;
  • 29
  • [ 375-73-5 ]
  • [ 778-24-5 ]
  • [ 142294-81-3 ]
YieldReaction ConditionsOperation in experiment
90.5% at 0℃; for 0.5h;
  • 30
  • [ 1145-98-8 ]
  • [ 3839-31-4 ]
  • [ 778-24-5 ]
  • [ 4098-97-9 ]
  • [ 18753-27-0 ]
YieldReaction ConditionsOperation in experiment
1: 10 % Spectr. 2: 25 % Spectr. 3: 10 % Spectr. In tetrahydrofuran at 4℃; for 192h;
  • 31
  • [ 3839-31-4 ]
  • [ 766-77-8 ]
  • [ 5272-18-4 ]
  • [ 778-24-5 ]
  • [ 1145-98-8 ]
YieldReaction ConditionsOperation in experiment
1: 26 % Chromat. 2: 38 % Chromat. 3: 6 % Chromat. 4: 2.5 % Chromat. With oxygen In tetrahydrofuran at 0℃; for 0.0166667h; Further byproducts given. Title compound not separated from byproducts;
  • 32
  • [ 3839-31-4 ]
  • [ 5272-18-4 ]
  • [ 778-24-5 ]
  • [ 1145-98-8 ]
  • [ 56-33-7 ]
YieldReaction ConditionsOperation in experiment
1: 26 % Chromat. 2: 38 % Chromat. 3: 6 % Chromat. 4: 0.3 % Chromat. With oxygen In tetrahydrofuran at 0℃; for 0.0166667h; Title compound not separated from byproducts;
  • 33
  • [ 768-32-1 ]
  • [ 75-76-3 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
at 40℃;
at 60℃;
  • 34
  • [ 778-24-5 ]
  • [ 71-43-2 ]
YieldReaction ConditionsOperation in experiment
100 % Chromat. With ammonia; iron(III) chloride; sodium amide at 20℃; for 0.05h;
98 %Chromat. With potassium trimethylsilonate In dimethyl sulfoxide at 70℃; for 6h; Sealed tube; Schlenk technique;
  • 35
  • phenylmagnesium bromide [ No CAS ]
  • [ 768-33-2 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
In diethyl ether at 20℃; for 15h;
  • 36
  • [ 766-77-8 ]
  • [ 71-43-2 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
71% With (hydridotris(3,5-dimethylpyrazolyl)borate)PtMe2H at 200℃; for 24h;
61% With norbornene; [Ir(hydride)2(1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene)(pyridine)3][BF4] In tetrahydrofuran at 110℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique;
  • 37
  • [ 13029-09-9 ]
  • [ 768-33-2 ]
  • [ 13688-68-1 ]
  • [ 778-24-5 ]
  • 5-methyl-5-phenyl-5H-dibenzo[b,d]silole [ No CAS ]
  • 38
  • [ 766-77-8 ]
  • [ 1111-74-6 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
With carbon dioxide; [(1,3-bis(3-tBu-5-Me-2-oxy-benzyl)-4-Me-MeOC6H2]Zr(CH2Ph)2; tris(pentafluorophenyl)borate In benzene-d6 at 20℃; for 0.25h; Title compound not separated from byproducts;
  • 39
  • [ 778-24-5 ]
  • [ 1626-24-0 ]
  • [ 1074-29-9 ]
  • [ 1613-66-7 ]
YieldReaction ConditionsOperation in experiment
1: 6 % Chromat. 2: 6 % Chromat. 3: 11 % Chromat. With aluminium trichloride at 110 - 120℃; for 3h;
  • 40
  • [ 56-33-7 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran; various solvent(s) / 6 h / 0 °C 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C
  • 41
  • [ 3839-31-4 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 74 percent / tetrahydrofuran; benzene-d6 / 16 h / Ambient temperature 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C
Multi-step reaction with 2 steps 1: 38 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C
Multi-step reaction with 2 steps 1: 38 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C
Multi-step reaction with 3 steps 1: 0.3 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C 2: tetrahydrofuran; various solvent(s) / 6 h / 0 °C 3: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C
Multi-step reaction with 2 steps 1: 45 percent Spectr. / 1,2-dibromoethane / tetrahydrofuran; diethyl ether / 0 °C 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C
Multi-step reaction with 3 steps 1: 35 percent / tetrahydrofuran / 1 h 2: 74 percent / N-bromosuccinimide / CCl4 / 48 h / Heating 3: 50 percent Chromat. / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) RT, 1 h

  • 42
  • [ 768-33-2 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 74 percent / tetrahydrofuran; benzene-d6 / 16 h / Ambient temperature 3: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C
Multi-step reaction with 2 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C
Multi-step reaction with 3 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 38 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C 3: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C
Multi-step reaction with 2 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 6 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C
Multi-step reaction with 3 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 38 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C 3: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C
Multi-step reaction with 4 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 0.3 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C 3: tetrahydrofuran; various solvent(s) / 6 h / 0 °C 4: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C
Multi-step reaction with 2 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 6 percent Chromat. / O2 / tetrahydrofuran / 0.02 h / 0 °C
Multi-step reaction with 3 steps 1: Li / tetrahydrofuran / 6 h / 0 °C 2: 45 percent Spectr. / 1,2-dibromoethane / tetrahydrofuran; diethyl ether / 0 °C 3: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C
Multi-step reaction with 2 steps 1: 59 percent / Li / tetrahydrofuran / 4 h 2: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C
Multi-step reaction with 3 steps 1: 89 percent / NaHCO3, H2O / acetone / 1 h / 0 °C 2: tetrahydrofuran; various solvent(s) / 6 h / 0 °C 3: 10 percent Spectr. / tetrahydrofuran / 192 h / 4 °C

  • 43
  • [ 778-24-5 ]
  • 1,3-bis(dimethylphenylsiloxy)-2,4-bis(dimethylphenylsilyl)-1,3-dioxo-1λ6,3λ6-dithiete [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90.5 percent / 0.5 h / 0 °C 2: 1.6 M nBuLi / tetrahydrofuran; hexane / 1) -40 deg C, 60 min, 2) to r.t., 60 min
  • 44
  • [ 79035-77-1 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 74 percent / N-bromosuccinimide / CCl4 / 48 h / Heating 2: 50 percent Chromat. / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) RT, 1 h
  • 45
  • phenylmagnesium chloride [ No CAS ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 83.4 percent / tetrahydrofuran / 1 h / 90 °C 2: 3.9 percent / tetrahydrofuran / 2 h / 50 °C
  • 46
  • [ 24964-64-5 ]
  • [ 778-24-5 ]
  • [ 403-42-9 ]
  • 3-[3-(4-fluorophenyl)-3-oxo-1-propenyl]-benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine In dichloromethane 17.A Step A: Step A: Preparation of 3-[3-(4-Fluorophenyl)-3-oxo-1-propenyl]-benzonitrile Triflic acid (3.2 g, 21 mmol) is added portionwise to diphenyldimethylsilane (2.22 g, 10.5 mmol) in 20 mL of dichloromethane and stirred for 1 hour. After cooling to -78° C., diisopropylethylamine (1.42 g, 11 mmol) and 4'-fluoroacetophenone (1.38 g, 10 mmol) are added and the reaction mixture stirred for another hour before adding 3-cyanobenzaldehyde (1.0 g, 7.62 mmol). After the reaction mixture is stirred 18 hours, it is diluted with 100 mL of dichloromethane and stirred 1 hour with a saturated solution of sodium bicarbonate. The organic layer is separated, dried (MgSO4), concentrated and columned over SiO2 eluding with dichloromethane to provide 0.8 g of the title compound; mp 170°-172° C.
  • 47
  • cis-bis(phenyldimethylsilyl)bis(triethylphosphine)platinum(II) [ No CAS ]
  • [ 768-32-1 ]
  • [ 778-24-5 ]
  • [ 1145-98-8 ]
YieldReaction ConditionsOperation in experiment
1: 24.1% 2: 13.5% 3: 42.4% In benzene-d6 heating in benzene-d6 soln. in a sealed NMR tube (80°C, 40 h); further product: polymers;
  • 48
  • cis-bis(dimethylphenylsilyl)bis(methyldiphenylphosphine)platinum [ No CAS ]
  • [ 67-64-1 ]
  • [ 768-32-1 ]
  • [ 778-24-5 ]
  • [ 1145-98-8 ]
YieldReaction ConditionsOperation in experiment
1: 27% 2: 13.3% 3: 34.1% 80°C, 31 h;
  • 50
  • [ 931-53-3 ]
  • cis-bis(dimethylphenylsilyl)bis(methyldiphenylphosphine)platinum [ No CAS ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
17.5% 100°C, 15 h;
  • 52
  • cis-{PdMe2(PMePh2)2} [ No CAS ]
  • [ 776-76-1 ]
  • [ 778-24-5 ]
  • [ 7440-05-3 ]
YieldReaction ConditionsOperation in experiment
In benzene (N2), dried solvents, room temp., gas evolution, Pd separates; SiMe2Ph2detected by GC, Si2Me2Ph4 is not formed;
  • 54
  • [ 33085-81-3 ]
  • [ 778-24-5 ]
  • [ 108008-86-2 ]
  • [ 108008-82-8 ]
  • (Si(CH3)2(C6H5)2)2Cr2(C10H8) [ No CAS ]
YieldReaction ConditionsOperation in experiment
0% In tetrahydrofuran byproducts: naphthalene; sealed glass ampule with (C10H8)2Cr, Ph2SiMe2 and dried THF was heated in a boiling water bath for 1 h with occasional agitation; under rigorous exclusion of the atmosphere; evapd., naphthalene and byproducts were removed by vac. sublimation, final residue was carefully sublimed yielding the mixt. of the products, total yield 16%; high-resolution mass spectral anals.;
  • 55
  • [ 768-32-1 ]
  • [ 1450-14-2 ]
  • [ 75-76-3 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In neat (no solvent) byproducts: benzene; High Pressure; heating of (CH3)3Si(C6H5) at 300°C and 100 atm H2 pressure;;
With H2 In neat (no solvent) byproducts: benzene; High Pressure; heating of (CH3)3Si(C6H5) at 300°C and 100 atm H2 pressure;;
  • 56
  • cis-bis(dimethylphenylsilyl)bis(methyldiphenylphosphine)platinum [ No CAS ]
  • [ 768-32-1 ]
  • [ 778-24-5 ]
  • [ 1145-98-8 ]
YieldReaction ConditionsOperation in experiment
1: 82.9% 2: 0% 3: 0% With P(C6H5)2CH3 In benzene-d6 heating in benzene-d6 soln. in a sealed NMR tube (80°C, 40 h) with addn. of diphenylmethylphosphine (8 equiv. per Pt-complex); further products: polymers; detn. by GLC;
1: 81.3% 2: 0% 3: 0% With P(C6H5)2CH3 In benzene-d6 heating in benzene-d6 soln. in a sealed NMR tube (80°C, 40 h) with addn. of diphenylmethylphosphine (2 equiv. per Pt-complex); further products: polymers; detn. by GLC;
1: 65.6% 2: 12.6% 3: 5.2% With P(C6H5)2CH3 In benzene-d6 heating in benzene-d6 soln. in a sealed NMR tube (80°C, 40 h) with addn. of diphenylmethylphosphine (0.5 equiv. per Pt-complex); further products: polymers; detn. by GLC;
1: 50.3% 2: 27.2% 3: 12% With P(C5H6)2CH3 In benzene-d6 heating in benzene-d6 soln. in a sealed NMR tube (80°C, 40 h); further products: polymers; detn. by GLC;
1: 48.7% 2: 28.6% 3: 19.1% In benzene-d6 heating in benzene-d6 soln. in a sealed NMR tube (80°C, 40 h); further products: polymers; detn. by 1H-NMR;

  • 57
  • [ 37865-47-7 ]
  • [ 136266-28-9 ]
  • [ 766-77-8 ]
  • [ 17881-88-8 ]
  • [ 778-24-5 ]
  • [ 1449-63-4 ]
YieldReaction ConditionsOperation in experiment
1: 3% 2: 4% 3: 14% 4: 54% With methanol In benzene Irradiation (UV/VIS); irradiation of catenate in benzene containing an excess of methanol with a 110 W low pressure Hg arc lamp at room temp. under Ar for 1-4 h; identification by GC and GC-MS;
  • 58
  • [ 15279-31-9 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
87% With C6H5MgBr In not given
  • 59
  • [ 96647-88-0 ]
  • [ 778-24-5 ]
  • [ 75061-54-0 ]
  • [ 75061-50-6 ]
YieldReaction ConditionsOperation in experiment
1: 42% 2: 5% In 1,4-dioxane refluxing for 6.5 h (N2), evapn.; trituration, extn., filtered, pptn. of mono complex on cooling of filtrate, working up of residue from extn. gave bis complex; elem. anal.;
1: 26% 2: 7% In 1,4-dioxane Ar-atmosphere; refluxing for 6 h; evapn. (vac.), chromy. (Al2O3, CH2Cl2/petroleum ether), recrystn. (hexane); elem. anal.;
  • 60
  • [ 778-24-5 ]
  • [ 13007-92-6 ]
  • [ 75061-54-0 ]
YieldReaction ConditionsOperation in experiment
44% In tetrahydrofuran; diethylene glycol dimethyl ether heating at 150°C for 61 h (N2), chromy on silica gel (benzene), concn., pptn. with hexane, filtration, washing with hexane, drying in vac.; sepn. of mono complex by sublimation, chromy. on silica gel (benzene), concn., pptn. with hexane, washing with hexane, drying in vac., soln. in hot CHCl3, crystn. on addn. of petroleum ether and cooling; elem. anal.;
  • 61
  • dicobalt octacarbonyl [ No CAS ]
  • [ 778-24-5 ]
  • dimethyldiphenylsilane nonacarbonyltetracobalt [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% In hexane; n-heptane Ar-atmosphere; stoich. amts., refluxing in hexane/heptane=2:1 v/v for 24h; chromy. (Al2O3, CH2Cl2/petroleum ether), recrystn. (hexane); elem. anal.;
In hexane Ar-atmosphere; stoich. amts., refluxing;
  • 62
  • [ 3839-31-4 ]
  • [ 583-55-1 ]
  • [ 544-97-8 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: dimethyl(phenyl)silyl lithium; dimethyl zinc(II) In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: 1-Bromo-2-iodobenzene In tetrahydrofuran; hexane at 20℃; for 16h; Further stages.;
  • 63
  • [ 1120-90-7 ]
  • [ 778-24-5 ]
  • 3-(dimethylphenylsilanyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With pyridine; palladium diacetate; lithium chloride at 20℃; for 24h;
  • 64
  • [ 636-98-6 ]
  • [ 778-24-5 ]
  • [ 1032070-14-6 ]
  • [ 98-95-3 ]
YieldReaction ConditionsOperation in experiment
45% With pyridine; palladium diacetate; lithium chloride at 20℃; for 24h;
  • 65
  • [ 13329-40-3 ]
  • [ 778-24-5 ]
  • [ 98-86-2 ]
  • 1-(4-(dimethyl(phenyl)silyl)phenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With pyridine; palladium diacetate; lithium chloride at 20℃; for 24h;
  • 66
  • [ 3058-39-7 ]
  • [ 778-24-5 ]
  • 4-(dimethylphenylsilanyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With pyridine; palladium diacetate; lithium chloride at 20℃; for 24h;
  • 67
  • [ 619-44-3 ]
  • [ 778-24-5 ]
  • [ 93-58-3 ]
  • 4-(dimethylphenylsilanyl)benzoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With pyridine; palladium diacetate; lithium chloride at 20℃; for 24h;
  • 68
  • dicarbonyl(cyclopentadienyl)methyliron(II) [ No CAS ]
  • FpSiMePh2 [ No CAS ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
In benzene-d6 for 20h; UV-irradiation; Inert atmosphere;
  • 69
  • [ 768-92-3 ]
  • [ 768-32-1 ]
  • [ 780-68-7 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
With C14H19Si2(1+)*C24BF20(1-) at -10 - 20℃;
  • 70
  • [ 101-84-8 ]
  • [ 778-24-5 ]
  • [ 18733-65-8 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: diphenylether With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at 20℃; for 16h; Inert atmosphere; Stage #2: Dimethyldiphenylsilane In tetrahydrofuran; diethyl ether; hexane at 20℃; for 16.67h; Inert atmosphere;
  • 71
  • [ 591-51-5 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diethyl ether 2: H2 / neat (no solvent)
  • 72
  • [ 108-86-1 ]
  • [ 185990-03-8 ]
  • [ 778-24-5 ]
  • [ 24388-23-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane With potassium methanolate In 1,2-dimethoxyethane at 30℃; for 0.166667h; Inert atmosphere; Stage #2: bromobenzene In 1,2-dimethoxyethane at 30℃;
Stage #1: bromobenzene With potassium methanolate; chlorobenzene In 1,2-dimethoxyethane at 30℃; for 0.0833333h; Inert atmosphere; Glovebox; Sealed tube; Stage #2: dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane In 1,2-dimethoxyethane at 30℃; for 0.0166667h; Inert atmosphere; Glovebox; Sealed tube;
  • 73
  • [ 1493-13-6 ]
  • [ 778-24-5 ]
  • [ 27607-78-9 ]
YieldReaction ConditionsOperation in experiment
96% at 0 - 20℃; for 0.5h; Inert atmosphere; Schlenk technique;
  • 74
  • [ 676-58-4 ]
  • [ 80-10-4 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
82% In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
  • 75
  • [ 2386-64-3 ]
  • [ 80-10-4 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
99% In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
  • 76
  • C70H92K4Li2O7 [ No CAS ]
  • [ 768-33-2 ]
  • [ 108-88-3 ]
  • [ 778-24-5 ]
  • [ 17938-20-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C70H92K4Li2O7; toluene In tetrahydrofuran at -78 - -40℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: phenyldimethylsilyl chloride In tetrahydrofuran at -40 - 20℃; Inert atmosphere; Schlenk technique;
  • 77
  • bromobis(triphenylphosphine)phenylpalladium(II) [ No CAS ]
  • [ 185990-03-8 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
90% In toluene at 80℃; for 12h; Sealed tube;
  • 78
  • [ 108-86-1 ]
  • [ 185990-03-8 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
88% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 80℃; for 12h; Sealed tube;
  • 79
  • [ 18666-25-6 ]
  • [ 917-54-4 ]
  • C20H19(2)HSi [ No CAS ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: benzyl methyl diphenylsilane; methyllithium In tetrahydrofuran; diethyl ether at -78 - -30℃; for 20h; Stage #2: With deuteromethanol In tetrahydrofuran; diethyl ether
  • 80
  • [ 108-86-1 ]
  • [ 3839-31-4 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
69 %Chromat. In tetrahydrofuran at 30℃; for 1h; Inert atmosphere; Typical Procedure for Silyl Substitution Reaction with SilyllithiumReagent General procedure: vial with a screw cap and a silicon-coated rubber septum wasconnected to a vacuum/nitrogen manifold through a needle,and it was evacuated and refilled with nitrogen three times. Dimethylphenylsilyllithium (0.4 M in THF, 2.5 mL, 2.0 equiv)was added to the vial under nitrogen atmosphere. 1-Bromo-3,5-dimethylbenzene (93.5 mg, 0.51 mmol) was added to the vial,then stirred at 30 °C. After 1 h, the reaction mixture was analyzedby GC to check completeness of the reaction. When thereaction was complete, H2O was added and the mixture wasextracted three times with Et2O. The organic layer was washedwith water and the combined organic layer was then dried overMgSO4 followed by filtration and evaporation. The crudeproduct was purified by silica-gel column chromatography with hexane eluent, then further purified by gel permeation chromatographyto give 3da in 63% isolated yield (76.5 mg, 0.318mmol).
  • 81
  • [ 108-86-1 ]
  • [ 3839-31-4 ]
  • [ 92-52-4 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
1: 48% 2: 8% In tetrahydrofuran at 30℃; for 1h; Inert atmosphere; Typical Procedure for Silyl Substitution Reaction with SilyllithiumReagent General procedure: vial with a screw cap and a silicon-coated rubber septum wasconnected to a vacuum/nitrogen manifold through a needle,and it was evacuated and refilled with nitrogen three times. Dimethylphenylsilyllithium (0.4 M in THF, 2.5 mL, 2.0 equiv)was added to the vial under nitrogen atmosphere. 1-Bromo-3,5-dimethylbenzene (93.5 mg, 0.51 mmol) was added to the vial,then stirred at 30 °C. After 1 h, the reaction mixture was analyzedby GC to check completeness of the reaction. When thereaction was complete, H2O was added and the mixture wasextracted three times with Et2O. The organic layer was washedwith water and the combined organic layer was then dried overMgSO4 followed by filtration and evaporation. The crudeproduct was purified by silica-gel column chromatography with hexane eluent, then further purified by gel permeation chromatographyto give 3da in 63% isolated yield (76.5 mg, 0.318mmol).
  • 82
  • [ 778-24-5 ]
  • [ 92-52-4 ]
YieldReaction ConditionsOperation in experiment
67% With tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); o-tetrachloroquinone In chloroform at 60℃; for 10h; Inert atmosphere; 3. General procedure for homocoupling reaction by Pd/o-chloranil catalysis General procedure: To a screw-capped glass tube containing a magnetic stirrer bar were addedaryltrimethylsilane 1 (0.30 mmol, 1.0 equiv), Pd(CH3CN)4(BF4)2 (3.3 mg, 0.075 mmol, 2.5mol%), CHCl3 (1.5 mL) or CHCl3/1,2-dichloroethane (1:4, 1.5 mL) and o-chloranil (55.9 mg, 0.225 mmol, 0.75 equiv) under a stream of nitrogen. After stirring at 60 °C for 10 hours, thereaction mixture was cooled to room temperature, and then passed through a short pad of silicagel (eluent: CHCl3). After the organic solvent was removed under reduced pressure, the residuewas purified by flash column chromatography on silica gel to yield biaryl 2. The reactions wereconducted in 0.50 mmol scale for 1a in 2.5 mL of CHCl3, 0.30 mmol scale for 1b-1t in 1.5 mLof the indicated solvent, and 0.20 mmol scale for 1w in the indicated solvent, respectively.
  • 83
  • [ 100-58-3 ]
  • [ 768-33-2 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
97% With (DrewPhos)<SUB>2</SUB>PdI<SUB>2</SUB> In diethyl ether at 20℃; for 24h;
  • 84
  • [ 462-06-6 ]
  • [ 768-33-2 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: phenyldimethylsilyl chloride With lithium In tetrahydrofuran at 0℃; for 6h; Inert atmosphere; Stage #2: fluorobenzene In tetrahydrofuran at -25℃; for 20h; Inert atmosphere; Schlenk technique; Sealed tube; regioselective reaction;
  • 85
  • [ 462-06-6 ]
  • [ 185990-03-8 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
58% With sodium t-butanolate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
  • 86
  • [ 591-50-4 ]
  • [ 766-77-8 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
75% With lithium acetate In N,N-dimethyl acetamide at 100℃; for 16h; Inert atmosphere;
  • 87
  • [ 17909-51-2 ]
  • [ 778-24-5 ]
YieldReaction ConditionsOperation in experiment
89% With bis(1,5-cyclooctadiene)nickel(0); 1,10-Phenanthroline In toluene at 160℃; for 18h; Glovebox; Inert atmosphere; Sealed tube;
83% With bis(1,5-cyclooctadiene)nickel (0); tributylphosphine; zinc In toluene for 36h; Inert atmosphere; Sealed tube; Heating;
Same Skeleton Products
Historical Records